For clarity (and personal sanity), I’ve mapped the unspoken stages of the almost-relationship:

Changing his number to a name

Goodbye 10 digits, hello Josh Hinge. You’ve decided he’s going to be in your life long enough to warrant a contact name. It’s small, but it’s not nothing. Cheers for making it this far (administratively). Emotional implications pending.

The Couch Shift

At some point, you move from sitting upright at a dimly lit cocktail bar in tight jeans to lying horizontally on a couch in sweatpants. This is where real life starts. A cuddle may or may not be in order. You’ll watch a random movie like Night at the Museum.

The Day Date Spectrum

Not all day dates are created equal. A coffee walk? Casual. A planned Saturday afternoon together? Intentional. A full Sunday hang that starts with a Saturday sleepover? You’re in deep.

The phone call

Anyone can text a “haha.” Texting can cosplay intimacy pretty convincingly. But a phone call, on the other hand, requires effort, presence, and a baseline level of emotional availability. No disappearing behind the guise of ‘plans.’ No chatphishing. Just you two.

The first planned sleepover

Not the accidental “we both fell asleep after a night out.” There’s an overnight bag, a charger, and a designated toothbrush. There’s something strangely intimate about seeing what’s in his toiletry bag (so cutsie). Needless to say, this is where you learn things…and figure out how to get a good night’s sleep next to each other.

Cooking for each other

You’ve moved beyond restaurants into domesticity. Someone is arranging tomatoes, mozzarella, and basil into flower shapes on pre-made pizza crust. Che La Luna is playing in the background. *Respectfully, this is also wifey behavior. Proceed with discernment.

Meeting his friends

You’re no longer a standalone experience. You’re being integrated into his life. His friends are forming opinions. You’re learning who else he chooses to spend his time with, and how you fit into that.

And if you don’t ever meet the friends? That is a (not so subtle) signal too.

Running errands together

You’re doing mundane things, together, on purpose? That’s not casual. Shared Trader Joe’s run sounds pretty relational to me. Romance in the frozen foods aisle <3 I hope he picks up some Kimbap.

Defining the relationship (the exclusivity convo):

In these digital and noncommittal conditions, clarity doesn’t just happen. You have to create it, rather than avoid it. You’ll survive, and beautiful new beginnings may start! Or not—in which case, at least the ambiguity has run its course, and you can stop asking ChatGPT to psychoanalyze your situation.

Of course, none of these milestones replace the fundamentals: consistency, reciprocity, consideration, and how they make you feel over time.

What did I miss?

Good luck out there <3

–Cait xo

Subscribe now

P.S.

Song of the week:

Articles I’ve enjoyed:

Lindsey Hall Writes

I Stumbled Across My Boyfriend's ChatGPT and It Ended Our Relationship

I find out my now ex-boyfriend had been questioning his feelings and attraction to me in the most dystopian, laughably modern way possible: ChatGPT…

Read more

2 months ago · 21225 likes · 2237 comments · Lindsey Hall

overdressed + overanalyzed

Charlotte York was right, I fear

A few weeks ago I came across a diagram on the internet that rearranged my brain chemistry…

Read more

3 months ago · 1470 likes · 164 comments · sarah dewald

Favourably Speaking

How To Have A Girlfriend And Not Suck At It.

Read more

2 months ago · 133 likes · 23 comments · Favour

MYLEIK

You’re Allowed to Have Fun While You Figure It Out

I’ve noticed something about hard seasons: people start editing their lives down to the essentials, and fun is usually the first thing to go…

Read more

2 months ago · 4715 likes · 98 comments · MYLEIK.

Secondhand Therapy

Stop Calling It Experience. It's Just Fear.

There’s a very specific thing that happens around year three or five or ten of doing the same job (or career). Maybe it’s sooner for you, maybe it takes longer. But at some point, several years in, you get good, or good enough. It’s around here that that steep learning curve…

Read more

2 months ago · 10 likes · 2 comments · haley rose

It was spring 2025, and I was meeting Ben at a cocktail bar in Central Square. He owned a software business, and we had similar backgrounds, so I was feeling open-minded.

Within minutes, he brought up fractals.

He told me they were the most beautiful thing in the universe because they are theoretically infinite. Transparently, I had no idea what he was talking about, but I nodded along like I did. As a former Sociology major (with a natural inclination for nosiness), this is one of my favorite parts of dating: understanding what people care about and how they make sense of the world.

And Ben? Ben loved a system.

Listening to him talk about patterns and structure, I realized that he had a very rational, almost clinical way of thinking. My friend Penny likes to call this boy brain. It might be black and white, but it’s also…effective. Decisively practical.

Which was exactly what I needed.

Because for months, I had been stuck on a question: should I move to London? It wasn’t that I lacked information. It was that I had too many competing narratives in my head. I could picture it all: the novelty, the adventure, the European weekends, but also the loneliness, the logistical chaos, and the daunting reality of starting over.

So I asked Ben what he would do:

He said: pick five criteria that matter most and use them to filter the decision.

That was it. Simple.

-

Later that summer, I went to London to take the decision seriously.

Naturally, I did not. I found myself still deeply undecided:

• yes: after a good sausage roll and a sunset spent on Primrose Hill

• no: after spending £15 on porridge and witnessing multiple British men casually wee in public (a surprisingly common occurrence)

Until one day, walking through Richmond, I finally gave Ben’s framework a try. I wrote down the five things that mattered most:

1. Proximity to people I love

2. Affordability of my lifestyle

3. Career growth potential

4. Access to travel and new experiences [✓]

5. Overall quality of life

Then I evaluated London. And it checked exactly one box. Just one.

And just like that, the decision that had been living rent-free in my brain for months was neatly put to rest in my Notes app.

-

I never saw Ben again.

Somewhere between the fractals, his inability to properly walk down the stairs (he had just completed a 1000-squat challenge with his Bulgarian gym buddy), and our chemistry-less first kiss, it just wasn’t meant to be.

But his decision-making framework stuck.

My friend Sharon once told me she treats mediocre first dates like informational interviews. Even when she knows there won’t be a second one, she stays curious, asks questions, follows the thread, even if it’s something random (like “commercial fishing or blacksmithing).” Curiosity for curiosity’s sake.

Worst case: you walk away with a story.

Best case: you get Ben’s five-point decision framework.

Not bad for a Tuesday night in Central Square.

—Cait xo

Subscribe now

P.S.

Song of the week:

Articles I enjoyed this week:

cue sheet

I Asked 67 People to Send Me a Song They Played On Repeat When They Were Crashing Out

Hello, friends! First of all, I want to thank you. I had no idea what to expect when I started this newsletter last month, and it’s been so soul-affirming to know that you’re all as nosy and sentimental as I am…

Read more

6 months ago · 839 likes · 61 comments · Jules Zucker

Notes from Hannah

32, not flirty, but still thriving

I used to think I needed certain things to live a life worth romanticizing. Cool friends that invite me out for drinks on a Wednesday night. An impressive job at a big company. Wine-heavy conversations held by candlelight with a guy I can’t stop thinking about…

Read more

6 months ago · 181 likes · 55 comments · Hannah

✩ not your polite newsletter

A BIG SIS GUIDE TO NOT EMBARRASSING YOURSELF IN 2026

I am going to hold your hand when I say this in the least shaming way possible — but you embarrassed yourself this year…

Read more

5 months ago · 2010 likes · 55 comments · ⋆˖ ࣪⭑ meredith ⋆˖ ࣪⭑

and got a question in the comments: How do you decide to continue seeing someone a few dates in when it’s not bad, but there’s not a strong spark?

My Saturn is returning, and I’m still partnerless, so I figured it was time to call in some reinforcements. I asked my married friends what actually matters in their relationships:

I’m truly so happy that my friends have found wonderful partners. But I want to point something out: none of them said I knew immediately.

And I think this is where a lot of us get it wrong. If you’re a decisive person, you may be on the lookout for certainty or perfection early on. Because that’s the ideal in your head, or because you’ve experienced it before. But the fact of the matter is: meaningful relationships don’t have to start that way. Sometimes it’s just fine, and then good, and then, slowly, something more.

I’ll say this from my own experience: the only situationships where I’ve felt that immediate wow feeling have ended quickly, and usually with me getting hurt. There may have been chemistry, but not much substance, and little interest on their part in building any kind of emotional intimacy. At the end of the day, that’s not who’s going to hear you out during an argument or support you through difficult times.

So rather than asking yourself am I obsessed in early dating, I think the better questions are: Am I comfortable to be myself? Am I curious to see where this could go? Is there a part of me that’s excited to see them again? Do I feel calm?

If the answers are yes, honestly, that might be enough to keep going.

And I’m going to go one step further here. If you’re someone who tends to make quick calls (usually towards no), I think some self-reflection is due. Are you actually open to love? Are you emotionally available to accept and reciprocate someone’s effort and energy? If so, get clear on a few (reasonable) non-negotiables. Hold onto those boundaries. And then challenge yourself to see what happens when you let something promising (but maybe not wow) build. See what happens when you take spark off its pedestal and allow curiosity to lead instead.

*If tend more towards comfortability in the what if (it’s me, hi), the challenge is more to trust yourself to recognize when it’s time to let go.

A helpful social scientific perspective for all this comes from Modern Romance, where Aziz Ansari underscores how individualistic dating has become.

Historically, people got married to build a life together. Often out of necessity but also with a shared understanding that: this is something we will grow into.

Today, we have endless options, longer periods of young adulthood, and stud mentalities out the wahzoo (the mindset of having lots of dating options). And with that comes a different kind of pressure: optimizing for a partner who feels like the best possible choice.

Even if a multitude of choices could ultimately lead to a positive outcome. Even if you’re overlooking something quietly good in pursuit of something loudly perfect.

To be clear, I am not suggesting settling. I want to feel something too. I just don’t think spark is the only way something meaningful begins, nor the most reliable signal of what will actually last.

In the words of my Italian coworker, I still believe in romantic love. But I’ve come to accept that, for me, it might show up in a steadier slow burn-y kind of way.

What do you think?

–Cait xo

Subscribe now

P.S.

Song of the week:

Articles I enjoyed this week:

Beyond Your Budget

The Boring Money Habits That Actually Improve Your Finances

At the beginning of a new year, motivation tends to spike all at once. You want to improve your health, your routines, your career, your relationships, and your finances - all at the same time. On paper, that sounds productive. In reality, it often leads to overwhelm, inconsistency, and burnout by early February (if not sooner…

Read more

5 months ago · 694 likes · 21 comments · Michela Allocca

First Rodeo

22 things that are, unfortunately, worth it

In my humble opinion, the things that are always worth the extra time, effort, or …

Read more

2 months ago · 257 likes · 26 comments · Azora Zoe Paknad

Frugal Chic®

You Don’t Need a Better Routine. You Need Agency

We all think we have main character energy, until we pause halfway through the day and realise we can’t quite remember when we actually made a decision for ourselves. The choices we make, the beliefs we hold, the values we keep - a lot of them feel inherited rather than chosen…

Read more

2 months ago · 124 likes · Mia McGrath | Frugal Chic®

angel cake

better sources of inspiration than pinterest

lately my days seem to be marked by a symphony of varying notification pings, my eyes feel trained to notice a digital flash indicating a new message, my entire world feels as if it resides in a intangible universe sitting idly in my pocket. i tend to feel this way when i do not carve out enough restorative time where i can comfortably exhale and allow …

Read more

2 years ago · 15677 likes · 188 comments · emily north

letters in the margins

a soft spring reset for people who don't want to reinvent themselves

I remember telling people how much I hate spring. The weather’s inconsistent, I hate spring cleaning and bugs are starting to emerge. It also signifies the end of something—winter, the school year—and I’m not someone who loves to watch things end and change. There’s also this quiet pressure to come out of winter as a whole new person. Someone who finall…

Read more

3 months ago · 83 likes · 7 comments · jordan b 💌

There’s an unspoken timeline to it. Kiss by date three. DTR by month three. Move in, or move on, by year three.

We question someone’s intentions if things progress too fast…or not fast enough. We (try to) let things go once they hit their invisible expiration date.

Since entering the dating world in earnest three years ago, I’ve felt unsettled by the pace of it all. It feels fundamentally at odds with who I am.

In my first serious relationship in college, we had the luxury of time. We were acquaintances first, then friends, and only then something more. When we started dating, there was already trust, context, and a shared world.

That’s the part that feels missing now: the social proof of it all.

When you meet someone on Hinge, the questions are immediate and binary: is this going somewhere, or not? Is it romantic, or not?

We’ve gotten very comfortable with accelerating intimacy to test compatibility, but we haven’t made the same room for the slower work of trust and understanding.

I’m pretty good (although not perfect) at knowing if it’s a heck no. But how am I supposed to know if it’s a heck yes after two drinks, a walk, and meeting your cat?

People who met their partners earlier in life weren’t forced to resolve this tension so explicitly. For example, one of my married friends described what she loves about her husband:

• He inspires me to grow

• He brings different interests into my life

• I love his friends. They reflect who he is

But the part I can’t stop thinking about came next: “He was my brother’s best friend. Knowing that someone I love and respect trusted him made it so much easier for me to trust and love him too.”

That’s it.

Her husband was, in essence, pre-vetted. Not just by her brother, but by time, by friendship, by community. She had seen who he was in other people’s lives before she ever had to decide what he would be in hers.

To be fair, I know slower doesn’t automatically mean better. Being friends first doesn’t necessarily mean longterm romantic compatibility. But what I’m getting at is that modern dating asks us to make decisions about strangers, quickly.

And that’s causing us to say no to people who could grow on us, and say yes (temporarily) to people who seem good on paper, but are actually just good at first dates.

Unfortunately, getting off the apps feels like exiting the dating scene. And we all know I can’t do that—how would the blog go on!?

But maybe there’s a middle ground I haven’t tried yet: less online dating, more building a life that lets me know people slowly, and lets dating happen within that.

In practice, this probably means I’m joining a Volo league.

—Cait xo

Subscribe now

P.S.

Song of the week:

Articles I’ve enjoyed this week:

Elle the Wingwoman

Lessons from the best flirt I know

I was catching up recently with a friend I’ll call Emma. We met in our early twenties when we were both living in Los Angeles and hungry for new connections (both platonic and romantic). We got together for the first time at the nicest cocktail bar we could afford, and spent many following weekends at sticky bars, sweaty clubs, and other young-person wa…

Read more

3 months ago · 1 like · Elle Wilson

christine's corner

6 months later: A sabbatical reflection

I quit my job in May 2025. I wanted to go independent. I wanted a spiritually aligned career. I wanted passive income and published assets. I wanted time and space for creative pursuits…

Read more

5 months ago · 514 likes · 81 comments · christineist

Open House

How to Make Your Weekdays Feel Like Weekends

For many of us, counting down the days until the weekend has been ingrained since we were kids. Monday is dreaded. Tuesday somehow feels worse. Wednesday means we’ve made it halfway. By Thursday we’re starting to thaw, and by Friday we finally feel like ourselves again…

Read more

3 months ago · 199 likes · 11 comments · paige kershaw

Recovering Girlboss

Staying invisible is costing you more than being cringe ever will

I’m writing to you from up in the sky, my favorite co-working space. But I’m editing this back in New York, where fake spring is officially here, it’s a cloudless 69 degrees today, and the sky is staying lit a little longer. I can taste the Hugo spritzes dancing on my tongue…

Read more

3 months ago · 1119 likes · 92 comments · Juliette Dallas-Feeney

Still Wandering

The death of the corporate job.

Last week, I had coffee with someone who works at a big consulting firm. She spent twenty minutes explaining her role to me. Not because it was complex, but because she was trying to convince herself it existed. "I facilitate stakeholder alignment across cross-functional workstreams," she said. Then laughed. "I genuinely don't know what that means anymo…

Read more

9 months ago · 18799 likes · 1467 comments · Alex McCann

I didn’t fully know what she meant, but I suspected she was right. She explained that the root chakra governs stability, belonging, feeling grounded in one place. Apparently, mine needed work.

Funnily enough, a few weeks earlier, the guy I was seeing had said something similar: he thought he was more stable than I was. He was a born and raised Mass-hole and had never seriously considered leaving beyond a brief stint in college. His life had continuity and a clear trajectory: the same city, the same childhood-turned-adult friends, the same dream he’d had since childhood to buy a house on the Cape. In contrast, I was dream-speaking with him about where I might go next.

At the time, I chalked it up to being fundamentally different people. Realistically, I wasn’t ready to become his Newton wifey at age 26. But in retrospect, I’m not sure the difference was just lifestyle. Stability, in his case, was about unwavering commitment to this version of life. And I’m not sure I’ve ever fully experienced that.

I’m very comfortable with ambiguity. I can picture multiple futures and hold space for all of them at the same time. I’ve started over enough to know that while difficult, it’s possible. And that flexibility has been useful.

But it has also come with a side-effect: an aversion to, or maybe even fear of, committing to any one trajectory. I’ve been in my current city for three years, and generally life is good. I have a lovely apartment and lovely friends. Still, I feel the pull toward something new.

I already know what you’re thinking. First, I should stop telling the guys I date about my plans to skedaddle, especially since I’m hoping to build something long-term. Interestingly, I seem to oscillate between people who are deeply rooted (and eventually frustrated by me) and people who are even more untethered, which comes with its own set of problems. And second, my life would probably be simpler if I stopped thinking about what if and threw myself into my present.

For context, I’m a third culture kid (TCK), someone raised outside the country listed on their passport. TCKs tend to develop a strong ability to adapt, along with a weaker attachment to place, and a fierce loyalty to forever friends and family. By age 18, I had lived in 9 different homes. I had gone from South Africa to Austria, and then a few US states, each move with its own version of starting over. I became a pro at being the new kid, understanding how to establish myself in new environments and use my exotism to my benefit.

It became a key part of my identity. And I think my upbringing is a big reason why I still feel oriented toward motion. I like the openness of it, the sense that there are still versions of my life I haven’t tested. If I’m being generous, I’ll call it a zest for experiences. It’s harder to admit that I might be pushing happiness or people away by having one foot out the door.

Recently, I read an essay by Kayla Doris about her chasing travel, only to realize she might not want to leave so much if she invested more deeply in the life she already had. So, she started pouring that same energy into the place she lived: building community, deepening friendships, committing to routines. And ultimately, it made her happier.

Reading her piece made me uneasy in the way good writing does sometimes. Does my instinct to keep moving reflect an inability to stay, or rather the absence of a person, place, or life that feels worth staying for?

According to my psychic, the prescription for a blocked root chakra is stability.

If I’m honest, I’ve probably been waiting for something external to make the decision to stay feel easier: a job I love or a perfect relationship.

If I take a step back, I think I’m coming around to the idea of staying put more than I used to be. But for now, I’m still interested in following my wanderlust, trusting that I’ll recognize something worth staying for when the time comes. And that I’ll be in the right mindset to choose it.

— Cait xo

P.S.

Song of the week:

Articles I enjoyed this week:

Aroona Chawla

how to pick your life partner (or: why you're probably doing it wrong)

there’s a version of this article that opens with a sweeping statement about love being the most important decision you’ll ever make, and you’ve read that article, and it didn’t change anything. so let’s skip that…

Read more

3 months ago · 132 likes · 28 comments · Aroona Chawla

Happy on Purpose

20 Things I've Learned from 20 Years of Marriage

Read more

4 months ago · 553 likes · 42 comments · Amelia Wilson

klose friends 💋

50 things that make me happy

Taking pictures of everything…

Read more

3 months ago · 17 likes · 4 comments · Karina

Petit Luxe

My Six-Month Journey to a Better Life

It was September 2025. My life looked completely different than it does today, and, thanks to a series of changes I have made, I have never been happier. Now, I don’t claim to have it all together nor am I pretending that everything is perfect now. Just that I have managed to get myself to a place where I can confidently say…

Read more

3 months ago · 313 likes · 12 comments · Meghan Hughes

Out of Office Adventures

What happened on my adult gap year

Most people associate gap years with 18- to 20-year-olds exploring the world before their university studies. When I decided to take a career break to travel at the age of 32, I worried I’d be the oldest person on the backpacker trail…

Read more

4 months ago · 47 likes · 40 comments · Claire Drinkwater

I’m excited today to launch a new advice column where readers can submit dating scenarios and questions here. Today’s submission:

What Actually Happened Here

Modern dating produces a specific kind of almost-relationship: one that ends before you have enough information to know whether or not it could have worked.

There’s just enough chemistry to spark your imagination, but then something interrupts the momentum. That’s the spark that got away.

Maybe she wasn’t feeling it. Maybe she wanted to date someone else. Maybe she decided to take a step back from dating overall. There are a million reasons why someone chooses to end something. But the simplest explanation is usually the right one: she had enough information to decide she didn’t want to keep going.

It’s natural to wonder whether things might have played out differently if timing had been better. When something ends before you’re ready, your imagination sometimes takes over. The story starts becoming about the relationship that might have been, rather than the person you knew. Try to remind yourself that the connection you experienced was the connection: awkward scheduling, waning momentum, and all.

All of that being said: it still stings.

Should You Reach Out Again?

My general rule is simple: if someone ends something, believe them the first time.

From what you described, she had the opportunity to keep exploring the connection and chose not to. I’d take that at face value and move forward.

Could there ever be a case to reach out again? Potentially. If several months pass and you still feel genuinely curious, sending a simple check-in message isn’t unreasonable.

But most of the time, the healthier move is to let it go and redirect your energy elsewhere, toward the people and connections that are actively choosing you.

This is also why in early dating (<3 dates), I generally recommend seeing multiple people at once. It naturally spreads your attention and keeps any single connection from carrying too much emotional weight before it has had time to develop.

The Bigger Lesson

Early dating requires alignment across so many variables: chemistry, communication style, availability, logistics, timing, emotional headspace, and what each person actually wants.

When even one of those pieces is out of sync, something that felt promising can fade quickly. That doesn’t mean the connection wasn’t real. It just means it wasn’t aligned enough to survive the realities of life.

The hard truth about early dating is that momentum is part of compatibility. If something can’t survive a few scheduling conflicts and a trip, it might not have been as strong as it felt in those first few dates. And that’s okay. Because the right connection for you will both spark upfront, as well as keep finding its way forward.

Thank you for writing in and sharing this <3

–Cait xo

Subscribe now

P.S.

If you have a dating question, I’d love for you to submit it here!

Song of the week:

Articles I’ve enjoyed this week:

espresso tonic

I quit a job in tech to become a yoga teacher

Three years ago, I was sitting on the rooftop of a yoga school in Tenerife. The sun was just rising, I had a beautiful view of the hills and the Atlantic, I was tanned, at peace, fuelled by local papayas and avocados, and excited about the future…

Read more

5 months ago · 272 likes · 34 comments · Anastasia

WORK AND MUSE

what ambitious girls should look for in a partner

I got married one month ago…

Read more

3 months ago · 1250 likes · 36 comments · JEEINYOUN

The Woke Salaryman

Career mistakes you seriously need to avoid in your twenties

DISCLAIMER: If this article looks familiar, it’s because we first published it on 18 Nov 2019. We’ve made some major edits to ensure it's still relevant in 2024…

Read more

2 years ago · 115 likes · 11 comments · The Woke Salaryman

Bits of Wonder

The problem of long-term close friendships

There was a point a year and a half ago when I felt I had found a community that would last forever. One best friend in the West Village, another best friend in the Upper East, an apartment with roommates that I loved coming home to. I wrote at the time, “I yearn for best friends that I’ll still be best friends with in 30 years…

Read more

3 years ago · 2492 likes · 46 comments · Kasra

Workbaby

Strategic people don't just think. They show their thinking.

You’re planning your one big summer trip for the year…

Read more

4 months ago · 283 likes · 17 comments · Soph | Workbaby

It had been about a year since my breakup, and I was having a hard time imagining myself romantically with anyone else. It didn’t help that I had developed the unproductive habit of checking my ex’s social media accounts a little too often. I hadn’t yet learned the value of the unfollow, and he hadn’t yet learned the importance of posting significant life updates, like his new relationship.

Fast forward a couple of weeks. I moved to a new city for my first ever big girl job and reconnected with a college friend Penny. She’s the one who ultimately delivered the news:

Conrad is seeing someone.

This news slapped me in the face. When our relationship ended, I felt it closed with the door ajar. My naivety had me romanticizing what it would be like to be together again, while his closure led him swiftly to someone else.

I felt a flurry of emotions. Dumb for holding onto something that had become one-sided. Confused by how quickly he seemed to move on from something that still weighed on me. And lastly, outpaced. Nothing exposes your healing timeline quite like your ex getting a new girlfriend.

So, I did what any emotionally stable woman would do.

I downloaded Hinge.

Suddenly, I had a pep in my step. I needed to get back out there. Emerge from my pit of woe. Prove to myself that I too could play this dating game. And maybe even fall in love again.

But, after judging everyone within a six-mile radius, and X’ing most of my likes with a “stud mentality"1 , I closed the app.

I confided in Penny. How do you go on so many dates, I asked her? I really couldn’t understand what she saw in these men. She seemed to enjoy collecting experiences, while I viewed profiles from a place of suspicion.

Look for green flags, she said, not red flags.

I nodded. In theory, it sounded enlightened. In practice, it turned my instincts on their head.

It’s my nature to look for red flags. I’m a Jewish woman from an immigrant family. We scan for risk. We assess against our checklist. We discern.

Looking for green flags felt almost irresponsible. Like lowering my standards or willingly ignoring danger.

But that’s not what Penny meant.

She meant: stop dating with a bias for disqualification. Start being open to alignment.

So, over the last few years, I’ve been quietly collecting data on green flags from myself and friends.

Some are superficial or ridiculous. But attraction is mysterious, and the data speaks for itself.

• Dimples

• Clean nails

• Big ears

• Well-controlled rosacea

• Owns Salomons

• Wears gilets

• Drives Zambonis (niche, but compelling)

These don’t necessarily mean he’s your husband. But they mean you feel open, and that’s important.

Early green flags are simple: attraction, warmth, whether you feel relaxed around him. Does he remember what you say? Make plans and follow through? Do you feel calm, or confused?

The green flags that emerge later are behavioral. They tell you how someone might move through life with you.

• He walks you to your Uber. Gold star if he calls it for you.

• He brings you water without being asked.

• He’s understanding of your food allergies or medical issues, even if they inconvenience him.

• He cleans his sheets regularly, and has two pillows and a headboard.

• He’s perfectly happy to clean up after a dinner party while you talk to your friends. (Translation, he’ll share household duties with you in the future).

• He manages your luggage at the airport, and your friend’s luggage when she visits.

• He has a passport, eg he understands there’s a world beyond his immediate radius.

• He has sisters, meaning he has spent his formative years being corrected by women.

• He’s always down to get dessert.

• He has a non-reptilian pet, suggesting he can keep something else besides himself alive.

• He offers to shovel your car out of the snow, or turn it on early so it warms up before you drive to work.

• He thinks it’s cool that you like Taylor Swift.

• He introduces you to his friends and family in due course, incorporating you into his life.

• He makes you feel calm.

Really what I’m describing here is consideration. And even better: anticipatory care.

Would he hold up your future pregnant belly without being asked? [context: this TikTok video]

Would he be down to get matching customized Onitsuka Tigers on your trip to Japan?

Would he continue to bring you a cup of tea every morning, even 30 years from now? (This is one of the acts of service my dad continues to do for my mom)

Ultimately, it’s not actually about babies or sneakers or cups of tea. It’s about whether he delights in showing up in the ways that matter to you, from the small sentimental moments to the harder ones.

If you’re dating right now and burnt out from pickiness, try this instead: go on your next date looking for one behavioral green flag. That’s what actually might point you towards partnership.

–Cait xo

Subscribe now

P.S.

Song of the week:

Articles I enjoyed this week:

Secondhand Therapy

The Quit Matrix: A Framework

It’s been awhile since I’ve written one of my Arte of Finding a New Job Posts, and so I thought I’d throw out a little brief one for you all. Enjoy the below…

Read more

3 months ago · 1 like · haley rose

Railed

“If he wanted to, he would” & other bullshit dating rules

In the age of TikTok virality and social media influencers, everyone has started giving their two cents about what dating rules should be followed, what red flags you should look out for, and what guidelines every dater should follow to find true love. “My angel boyfriend is proof that if he wanted to, he would,” one creator recites. “Here is the exact …

Read more

6 months ago · 277 likes · 18 comments · Mia Sherin

Before Dinner

A human being exists for more than our entertainment, even online.

You sit down at dinner with a friend. They laugh and say, “Hey, look at this video of my sister getting body-slammed by the police. Do you recoil? Frown? Question it? I think all of us would find such a callous act heinous. Now imagine that you laugh and then begin passing the phone around. In fact, let’s say you take it a step further and connect the p…

Read more

4 months ago · 16 likes · 8 comments · Blake Barclay

Travel Guides & Itineraries

I cut out sugar for 30 days… what I’ve learned in the process

My morning coffees always had a splash of maple syrup, my midday matcha accompanied by a spoonful of honey, and I never skipped dessert at a new restaurant (all in the name of thorough “research”). I didn’t realize it before, but I was a sugar addict. Limiting sugar was the hardest thing I’ve ever done, and this small experiment made me realize that it …

Read more

3 months ago · 14 likes · 2 comments · Christine Le

postcards by hasif

How to be Whimsical

There’s a strange heaviness in the air lately, and I don’t mean just the literal weight of summer heat or political tension or whatever the internet is yelling about today. I mean this grayness, this invisible fog that seems to have blanketed the world not always in the sky, but in us…

Read more

a year ago · 9748 likes · 118 comments · hasif 💌

Hi Substackers,

Happy Wednesday from snowmageddon! This week, I’m kicking off a new series. Three years of dating in this city have taught me many things, including the ideal spots to get to know someone new.

Below, a curated edit of Boston dating destinations, from a self-proclaimed foodie and new experience enthusiast.

[drinks & apps or dinner]

Darling (Central Sq, Cambridge) | This might be my new favorite spot for drinks and dim sum. Trendy, lively, but not trying too hard. The Chinese-inspired cocktails are exceptional: order the ‘common trope’ (milk washed vodka, jasmine, lychee, black rice sake, cucumber). The glassware is so delicate, you’ll want to take a bite out of it. [First Date Approved]

Desnuda cocina & bar (South End, Boston) | Dim lights but still buzzy. Get the Dragon Kiss cocktail (citrus vodka, guava & dragon fruit puree, yuzu) and the tiradito de salmon. The downstairs lounge is a great part two to the evening, allowing for a seamless change of scenery. [First Date Approved]

Picco (South End, Boston) | Comfortable but still impressive. The Mushroom & Brie pizza and the Raspberry Chip ice cream are non-negotiable and made in-house. It’s the kind of place you’ll keep coming back to throughout your relationship, but also the perfect tone for your first dinner date. [Second+ Date Approved]

Si Cara (Central Sq, Cambridge) | The sweet spot between formal and casual. Great pizza spot (specifically the Lamb Sausage pizza) and right next door to New City Microcreamery for Baklava ice cream. Ideal for when you’re figuring out if this could become a thing. [Second+ Date Approved]

KAVA neo-taverna (South End, Boston) | Small, candlelit, and quietly romantic. Super intimate space, so if your date can get a booking, that man has planning prowess. And I’m impressed. The zucchini chips with tzatziki are top tier, and all the Greek-inspired small plates are designed to share. [Third+ Date Approved]

Gufo (East Cambridge) | Upscale yet understated. And so underrated. The bar is cozy, and the back patio in warm weather feels like a best kept secret. Start with the Half Chicken Milanese, split the Swiss Chard pizza, and absolutely get the vanilla ice cream with a magic shell for dessert. A strong choice when you’re past small talk and into substance. [Third+ Date Approved]

Mad Monkfish (Central Sq, Cambridge) | Sushi meets live jazz in a slightly chaotic yet charming way. This is more of a ‘we already think we like each other’ spot. Order the Rumpelstiltskin roll, enjoy the music, and debrief the show over ice cream at Toscanini’s (try the Milo flavor). [Fourth+ Date Approved]

Lola 42 (Seaport, Boston) | Polished and borderline clubby (in a good way). If that’s not your vibe, ask to sit outside overlooking the harbor. Get the CON-CU-BINE martini (cucumber vodka, sake, passion fruit, lychee) and Capt’n Jose sushi roll. This is a “dressing up” kind of date, so either that’s your man’s vibe or you two are getting more serious. [Fourth+ Date Approved]

[day dates]

Maruichi Select (Coolidge Corner, Brookline) | Meet at Maruichi for matcha (and maybe onigiri) and then walk over to Clear Flour Bread for a pretzel chocolate croissant. Simple, low stakes, and great for conversation. If you have a car, drive up to Corey Hill Park to enjoy your pastries with a view. [First Date Approved]

Brookline Lunch (Central Sq, Cambridge) | Retro diner energy. Baklava Pancakes. Need I say more? [Second+ Date Approved]

[activities]

The Esplanade | Effort without extravagance. I will always defend a sunset picnic date. It’s important to romanticize a Tuesday! And if he packs the snacks? Green flag. Find a bench because the geese own the grass. Mozey over to Night Shift after for a post-picnic drink. [First Date Approved]

Frog Pond Ice Skating (Boston Common) | Seasonal and cinematic. Built-in hand holding. Warm up after with a coffee from Tatte Boston Common or a walk down Newbury St for Swedish candy from Lil Sweet Treat. [Second+ Date Approved, assuming basic skating competence]

MFA Late Nights (Fenway, Boston) | Art, DJ, plastic cup of wine: surprisingly romantic. Wander the galleries and discover if you have the same museum style: are you are a stroller or do you stop to read every plaque? [Second+ Date Approved]

The Cannoli Test (North End, Boston) | Hit up the trifecta: Mikes, Modern, Bova’s. Debate your winner (there’s a correct answer). Continue the argument over drinks at Modern Underground or a comedy show at Improv Asylum. Playful disagreement is important. [Second+ Date Approved]

A yoga class (Beacon Hill Yoga, Boston Yoga Union, Corepower) | Intimate, slightly sweaty, can be telling. Not a first date move, but a subtle compatibility test once you’re a few weeks in. You’ll go to Fenway Park with him, so it’s his turn to show up for your interests. [Fourth+ Date Approved]

Pizza Night (your apartment) | A milestone. Observe keenly: Does he pre-heat the oven? Does he offer to clean? Does he help you cook? Or does he hover? The way someone behaves in your kitchen will tell you more than a three-hour dinner ever could. [Fifth+ Date Approved]

Red Sox Game (Fenway, Boston) | A Bostonian rite of passage. Glizzies, summer air, and collective cheering. Even if you don’t love baseball, it’s hard not to love the atmosphere. Shared experiences are important. [Fifth+ Date Approved]

–Cait xo

Subscribe now

P.S.

Song of the week:

Some articles I’ve enjoyed lately:

Diary of a High Achiever

To the woman who always knew she was meant for a bigger life

In life, some people are born with this indescribable knowing that they are different. A knowing that you’re meant to live a bigger life. That you have a lot of potential and you’re supposed to do great things…

Read more

6 months ago · 1279 likes · 22 comments · Sensi Charlery

Secondhand Therapy

Because saying no is the only way to get your life back.

I once watched a movie called Yes, Man, about a post-divorcee, bitter at the world, who fixes his miserable life by agreeing to absolutely everything. Yes to helping the homeless man, yes to helping with a bridal shower, yes, yes, yes. And, predictably, his series of life-affirming…

Read more

4 months ago · 6 likes · 2 comments · haley rose

Mia McGrath

5 ways to get dangerously ahead in your 20s

Hey! So glad you could be here at Frugal Chic, where financial intelligence meets taste. Today we are discussing crucial traits that have helped me get ahead in my 20s…

Read more

5 months ago · 428 likes · 16 comments · Mia McGrath | Frugal Chic®

✩ the city edit ✩

things that make me feel cool & hot & grown up

In the middle of a big move to NYC, I’ve fallen headfirst back into my early-2000s rom-com obsession with movies I loved as a little girl. There’s just something about the excitement and joy of these women (think: Andie Anderson, Jenna Rink & Andrea Sachs) that makes me so hopeful for this next chapter and so excited for who it is I’ll turn out to be wh…

Read more

4 months ago · 35 likes · 10 comments · ✩ the city edit ✩

marielle's marginalia

“she looks SO good for her age” and she’s literally 32…

I recently read Gabrielle Dubois Meloff’s recent article “The anti-facelift guide to aging well”, she describes a woman who spent nearly six figures surgically preserving the age where women are still allowed to be both desirable and respectable. Not chasing youth — chasing that one socially sanctioned middle ground where visibility doesn’t yet feel lik…

Read more

6 months ago · 60 likes · 17 comments · marielle stokes

I’ve done the research. I’ve polled the masses (group chats). And the data is clear.

You are up against: the ick.

In principle, an ick is usually just an excuse to end things with someone you weren’t that into anyway. But believe me when I say: we want to like you. We’re rooting for you.

Unfortunately, some of you are unintentionally working against yourselves.

Let’s get into it.

Hinge Violations

Your dating profile is your brand. You’re curating intrigue. And your target audience is women you want to date.

If you write that you’re looking for someone who will go to the gym with me, it reads like you’re looking for arm candy, not a relationship.

Anything centered around tequila, reconsider. Anything about deleting a food group together? Not romantic. Your typical Sunday described as football + hangover? No thanks.

Mirror pics. Fish pics. Gym pics. Voice notes (unless you are extraordinarily funny or briefly playing guitar in a way that feels charming). These are high-risk maneuvers that don’t communicate much depth.

And if your primary engagement strategy is liking photos without responding to prompts, you’re missing the opportunity. We gave you material. Using it can help you stand out.

Behavioral Red Flags

If you text at 5:30 pm asking what we’re doing at 7, you’re disqualified. Planning ahead signals that you value our time. Pick a place in advance. Make a reservation. This is not advanced calculus.

On the date, check in with yourself: have I asked her anything about herself? Have I been talking this whole time? Showing curiosity is important.

Stop commenting on other women’s appearances, positively or negatively. We do not need your running commentary on strangers or reality TV contestants.

If your mood is dependent on your favorite sports team’s performance, that’s worth dissecting.

If you pick pool over ocean, it’s a no.

If you lose at darts and sulk, embarrassing. If you win and won’t stop talking about it, worse.

If you go to a predominantly female workout class, awareness goes a long way. Please manage your presence and purchase a microfiber towel.

And if you graduated college during a previous administration and are still asking what sorority I was in, it’s time to evolve.

And digital behavior matters. Stop sending unsolicited selfies. Chill on the excessive emoji usage. Especially, the purple devil 😈, anything crying, or anything monkey 🙈🙉🙊. Emoticons, however, are acceptable in moderation. A well-placed “:)” is cute.

The Tragedy of Personal Style

You do not need to be trendy. You do not need to be edgy. You simply need to stop sabotaging yourself.

V-necks? Retire them. We did not consent to chest hair at 11am.

Athletic socks with Sperrys.

A leather jacket two sizes too small.

Toes out at dinner.

Puka shell necklaces in the continental United States.

Skinny jeans of any kind.

Jorts when you’re not at a music festival.

And then there’s facial hair malpractice. The neck beard. The soul patch. The chin strap.

We are not asking for perfection. We are simply asking for self-awareness. And while we’re here: please brush, floss, and use breath mints when needed.

Lifestyle Choices

Some choices carry cultural baggage, fair or not.

Men’s rights activists.

DJs.

If your entire personality is your private equity or consulting job.

Harvard Law students who want you to know immediately that they are Harvard Law students.

PhDs who feel the need to prove they’re smarter than you.

Any man who doesn’t value education.

Basic Human Decency

Be kind to waiters. If you are rude to someone handling our food, the date is over.

Drive. Or at least offer to. Making us drive feels “very baby girl of you”

Spell correctly. Respect food allergies. Take your shoes off if the house has a shoes-off policy. These are basic things.

And then, the fundamentals:

• Make a plan in advance

• Confirm it the day of

• Listen

• Walk us to the Uber

• Check that we got home safely

• Remember that we like sushi and suggest sushi next time

• Actually listen

• Communicate about your intentions, early

This is not grand romance. This is consideration. And consideration is hot.

Fin

The ick is rarely about the socks. It’s about what the socks suggest.

We don’t need perfection. We just need self-awareness. And to feel considered.

Boys, I hope this helps.

Green flags coming soon.

—Cait xo

Subscribe now

P.S.

Song of the week:

Some articles I’ve enjoyed lately:

Museguided

Ick, Interrupted

It always starts with a flicker. Not a red flag, those are too dramatic, too noble, too retro. No, the ick is a paper cut on your libido. Tiny, accidental, and somehow excruciating. One minute you are hypnotised by the curve of his jaw and the whisper of his voice in a dimly lit bar. The next, he’s saying “nom nom” while eating tacos and it’s like a priest just walked in mid-orgasm. Your body recoils before your brain has words for it. Suddenly, this man, who, an hour ago, had the tragic poet energy of someone you could have cried on, now looks like he high-fives after sex and collects Funko Pops. Something snaps. Not in him. In you. And there’s no going back…

Read more

a year ago · 264 likes · 201 comments · Tamara

Feeling! Magazine

Things To Do When You Don't Feel Good

Things To Do When You Don’t Feel Good…

Read more

4 months ago · 794 likes · 54 comments · Jenna O'Brien

Anna Mack's Stack

Why are ambitious women quitting their jobs?

I woke in the night to the sound of someone desperately gasping for air, and it took more than a few seconds to realise it was me…

Read more

4 months ago · 113 likes · 43 comments · Anna Mackenzie

beaches in manhattan

If Cities Were Boys You Date in Your Twenties

New York is the one everyone warns you about. He’s busy. He’s always busy. He’ll cancel on you twice in one week and then show up at midnight with a bottle of wine and an opinion about something you didn’t know you cared about until he said it. You’ll be angry a lot, at him and at yourself for staying. But then he’ll take you to a rooftop you’re definit…

Read more

5 months ago · 294 likes · 55 comments · shibby

Character

I burned down my social life and started again

If you enjoy this, consider hitting the like button. It feels good for me when you do, like seeing a smile or a head nod when you’re telling someone something, and it lets me know you’re here and I’m not just talking to myself…

Read more

5 months ago · 281 likes · 30 comments · Anne Benveniste

Honestly I’ve always loved this holiday. My mom still sends me care packages, and every year, I look forward to my little chocolate boyfriend. He’s reliably sweet and uncomplicated. Shelf-stable too.

I’ve spent most Valentine’s Days single. I know the script, and I love celebrating love in all its forms. But this particular year feels a bit different: I’m suddenly the only one in my close friend group who’s free Saturday night.

Ironically, I work full-time in marketing for a category that thrives this week. Our campaign promise is simple: buy the right gift [eg our product], and you too can prove that you genuinely get your partner.

This year, I’m giving myself the gift of an intentional weekend. It’s less commercially motivated, but I’m excited about it nonetheless.

My Valentine’s Day Weekend Non-Negotiables

Purposeful plans. “I’ll see how I feel” is how I lose entire days to the couch. Planning is romantic. This is step one.

Romanticize something small. Reading Modern Romance: An Investigation by Aziz Ansari in a new cafe. Trying Call Me Honey coffee shop that just opened in Cambridge. Ordering a pastry without negotiating with myself about it. (If you live in the Boston area, I highly recommend Clear Flour Bread!)

Streaming, strategically. *Watch in moderation so that self-soothing doesn’t morph into escapism. I just started Love Island: All Stars, so I’m excited to see where their heads are at this time.

Eat something heart shaped because it’s whimsical and cutsie

Call friends I miss. My friends are scattered across cities and time zones. I’ve learned that maintaining global friendships takes initiative, and this weekend is a great time for reconnection.

Go out! I texted an acquaintance who I thought might also be looking for plans, and now we have Saturday night sorted.

Make the vision board I keep saying I’ll get around to. I’ve already mapped out my one- and five-year goals. Now it’s time to translate them to Pinterest.

Call my mom so she can remind me there are statistically no eligible bachelors in Boston [this mindset is probably an issue…I’ll start working through it, next week lol]

An effortful dinner instead of defaulting to girl dinner. I recently had the loveliest evening at a married friend’s house. What struck me most was the intention of it all: a thoughtfully prepared meal, a fully set table, everyone sitting down together. I live alone and rarely go to that much effort for myself. But this weekend, that can change.

A solo movie. Normally I’d avoid rom coms this weekend, but Wurthering Heights (or maybe Jacob Elordi) is calling my name.

Something that makes me feel pampered: facial, nails, everything shower

Subscribe now

Wishing you all a thoughtful and fulfilling weekend! I’ll be ticking through my list with my chocolate boyfriend by my side.

Happy Valentine’s Day <3

–Cait xo

P.S.

Five articles I enjoyed reading this week:

Sideroad 38

the art of being happy (when you're not sure where you're going)

Felt somewhat lost at certain points in 2024. Wrote some notes to self. Here’s a compilation. Happy New Year and cheers to many more happy moments in 2025…

Read more

a year ago · 92 likes · 12 comments · Ines Lee

Secondhand Therapy

Your Obsession with FAANG Bites

GOD. I know. The hypocrisy is blinding…

Read more

4 months ago · 4 likes · 1 comment · haley rose

Your Brain on Money

Everything is private equity <3

I bought a dress for a wedding last month from Reformation. It was $350, which is more than I would normally spend on any item of clothing, but it was silk and I figured that I could wear it again…

Read more

4 months ago · 4026 likes · 179 comments · Hanna Horvath

Apsarā ⊱🪷⊰

how to start regulating your nervous system

As someone who was in chronic survival mode for almost 2 years and found my way out of that paradigm, I cannot believe that I still haven’t made a post solely on how to harmonize the nervous system. So, here it is…

Read more

8 months ago · 2646 likes · 58 comments · maneesha sem ‧₊˚ 🪷 . 𓂃

But you know what I don’t like?

Being single in aggressively couple-forward spaces.

Take weddings, for example. These are events that spotlight couple-hood, and I grew up loving them. Say Yes to the Dress? Seen every episode. I love the love stories and the symbolism of two lives intertwining. People finding their zivug (right match) and becoming chavruta (life companions).

But there’s something uniquely confronting about being at a wedding when you’re the only single person in attendance. I can’t help but feel like an outsider. My lack of accompaniment slaps me in the face in ways I don’t have to confront in everyday life.

There’s nobody to grab me a drink, offer me a suit jacket when it gets cold, split a hotel room charge, or tell me my hair looks nice. I’m the extra chair at a table full of couples. My life simply looks and moves differently than everyone else’s.

(As an aside, I hate to be the bearer of bad news, but rom coms lied to you. Singles tables do not exist.)

I used to think feeling a bit off at predominantly partnered weddings meant I was insecure about my relationship status. Now I think it just means I’m human, capable of being genuinely happy for couples while also acknowledging discomfort in otherness.

So instead of trying to pretend the feelings aren’t there, I prepare for them.

My Unofficial Survival Guide

• Pre-game, emotionally. Your conspicuous singlehood may stir up some emotions. I’d suggest running some mental simulations and deciding how you’re going to handle various situations. For example, slow song came on? Time for a strategic bathroom break or a chat with the bartender. I’d also suggest finding some consolation in a trusted friend beforehand. Solidarity helps.

• Have a dating-life script ready. “Are you seeing anyone?” will be the second question people ask you. A simple neutral response (“Nobody in particular, just enjoying life!”) is enough. You don’t owe anyone a TED Talk or exposé.

• Bring a cute wrap. Weddings are held exclusively in overly air-conditioned rooms. You’ll all get cold, and your friends’ boyfriends will offer suit jackets. This is a canon event. Bring your own outerwear and carry on.

• Say yes to a platonic plus-one if it’s offered. This could be its own essay: isn’t it strange that romantic partners (who the couple may barely know) are valued more than lifelong friends? Normalize bringing platonic besties to weddings.

• Accept your Airbnb fate early. If you’re sharing a house, you will probably get put on the couch. It’s annoying, but couples want rooms. It’s better to make peace with this now. One day, you too may claim a bedroom.

• Have Fun. Weddings are one of the rare moments when almost everyone important to a couple is in the same room. That’s special. Try to shift your focus to being there for them and enjoying catching up with people you don’t see often. This doesn’t erase your feelings, but it does push your energy outwards, instead of letting it spiral inward. Afterall, the event only lasts a few hours.

A Closing Thought

Mid-late twenties are where the great divergence happens. Half your friends will be married with a puppy and a baby on the way, and the other half just got ghosted by their situationship.

After spending most of my twenties unpartnered, I’m coming around to the idea that my timeline will look different to some friends’. And I may continue to lose the shared identity of singlehood with more and more friends as they pair off before I do.

At the same time, my very wise friend Ana says the word of 2026 is village. And I really agree with her. Because if romantic partnership isn’t an anchor in my life right now, community can be.

If you’re the single friend at the wedding, I hope some of this resonates. And if you have any other tips for resident single friends, I’d love to read them in the comments.

–Cait xo

Subscribe now

P.S.

Five articles I enjoyed reading this week:

• Why do we consider travelling as “living” when it’s the opposite?

• Ben from Hinge - by Maija Ariele Fiedelholtz - Crushing

• How to Succeed at Dating Events - by Elle Wilson

• The stable marriage problem

• I Tried the “Non-Corporate Girlie” Life and Now I Want a 9-to-5

I’ve always shied away from dating events because I didn’t want to believe I’d reached dating-event-level single. In hindsight, this fear is ridiculous; it’s not like the apps have been working for me anyway. Still, there’s a stigma against dating events that I used to buy into, as if being in attendance means you’ve reached desperation territory. My Met Through Friends experience totally changed my perspective.

Met Through Friends is a dating event series where attendees bring plus ones they’d vouch for. The premise is simple: everyone says they want to meet someone through friends, so why not create events that help make that happen? The vibes are curiosity, openness, and letting connections unfold naturally, which is a welcome break from Hinge dates where efficiency reigns supreme and there’s an assumed trajectory for the relationship before you’ve even had your first drink.

Bright eyed and bushy tailed, I recruited my brother’s college roommate Matt to be my plus one, and got ready for what felt like (dare I say) an exciting night of dating.

Met Through Friends, Boston

The event was held at Lou’s, a trendy cocktail bar in Harvard Square. When we walked in, @elle_the_wingwoman, the founder of Met Through Friends and a certified dating coach, immediately made us feel welcome. Matt and I grabbed drinks and scanned the attendees while waiting for the evening to kick off.

There were fifteen tables scattered around the room. The girls stayed seated, while the boys rotated every six minutes. Very quickly, I spotted a familiar face: a guy I recognized from Hinge. We’d orbited each other online and in real life for years without ever crossing the talking barrier, until that night.

By the end of the mini-dates, I’d identified three potential romantic prospects, made a couple of new friends, and even gained a Substack subscriber. After months of Hinge drought, this evening reminded me how fun it can be to have good conversations with strangers.

When cocktail hour rolled around, some of the attendees dipped, including two of my so-called prospects. I felt a brief twinge of disappointment. But that’s life in the IRL dating lane: rejection happens head-on and in real time, without the buffer of a phone screen. That pushed me to focus on prospect #3, who woo-ed me with easy conversation and indie charm, until he ghosted me a few days later. I don’t blame Met Through Friends though; they can’t be held responsible for modern dating’s bad habits.

Some Thoughts from the Field, For What It’s Worth

Exchanging numbers felt awkward

I’ve written before about how we've lost the ability to mingle1, and that showed up at this event. With just six minutes per mini-date, there wasn’t an obvious or natural moment to exchange contact info. Matt told me afterward that he was interested in a couple of girls but chickened out of asking for their numbers. I also wish I’d found a way to give my number to prospects #1 and #2.

This feels fixable with a little handholding:

• Have attendees prepare number cards before the mini-dates begin and explicitly encourage exchange

• Give a one minute ‘warning’ before each mini-date ends, so people feel prompted to pivot the conversation

• Use a ‘tick’ system where organizers exchange numbers post-event if interest is mutual

As much as I’d love for all of this to be organic, even the best dating events need to cater to a population that struggles with converting interest into follow through. A little extra structure feels not only acceptable, but necessary, IMO.

All the men were the plus one’s

Meaning: they were invited by their female friends to join. To me, this signals a few things:

• First, Elle is a genius. Outsourcing vetting to cool female friends is a brilliant way to get quality men to show up.

• Second, there’s something structural going on with men right now. Many won’t opt into dating events on their own volition, even when they say they want connection. I think it’s because dating events require a lot of vulnerability: a public admission that you’re looking for a partner, paired with the possibility of leaving empty handed. That kind of exposure can feel intimidating, so the buffer of a friend can help soften the potential blow.

We need to reframe the narrative around dating events altogether

When I told my friends about Met Through Friends, their first reaction was: were the guys super lame? FYI they weren’t, but that automatic cynicism is common, and it’s part of the problem. I found myself caveating well it’s for the blog (which is only half true), as if I needed an excuse to show up.

If we were all more accepting and enthusiastic about looking for connection in this way, dating events might feel less desperate and more like a socially encouraged way to meet someone cool. Ultimately, this reframe feels like a core JBTD if we want to make dating analog again.

Final Verdict: Worth It

If you’re deep in the trenches of Hinge and still looking for your person, a Met Through Friends event is absolutely worth attending. They can’t guarantee a match, but they can bring some humanity back to dating. I’m really glad I went.

–Cait xo

Subscribe now

*Before any resident comes for me, please read the disclaimer at the end. This is intended to be observational humor :)

Rankings are based on subject-matter expertise, text-to-ghost ratios, and future earning potential.

Tier 1: Would Date Again

-

Tier 2: Proceed with Caution

Internal Medicine

Known for taking extensive histories at work, which means he won’t ask you a single thing about yourself. He has already exhausted his curiosity for the day and will cancel your date last minute, then disappear forever. Loves to over-intellectualize everything and has an inflated ego. Probably trying to be a Cardiologist, but purely for the money.

General Surgery

Has a god complex, but it’s occupationally encouraged. Gets hazed by attendings and secretly enjoys it. Believes suffering builds character. Has the messiest apartment you’ve ever seen. Emotionally unavailable now, but will be rich one day, so you can decide what to do with that information. Super loyal when he wants to be, and often very charismatic too. Has a chip on his shoulder regarding his future salary—maybe should’ve done Plastics.

Orthopedic Surgery

Bro-y, hot, and goes to the gym religiously. Walks around like he’s always flexing and compliments other men on their lats. Thinks protein shakes count as dinner and still calls women chicks. Doesn’t care to know the difference between a diuretic and an antibiotic. If you do end up together, prepare to compete with Stryker reps for his attention. Driven and deeply committed, to himself.

Pediatrics

Caring, friendly, patient. Will make less money than he should but doesn’t have a chip on his shoulder about it. Too wholesome for this list…no obvious red flags, which is a red flag. *Double check that he’s straight though.

Anesthesiology

Went to medical school to master bedside manner, only to choose a specialty where all he does is supervise CRNAs and scroll on his phone. Frequently online shopping, doing crosswords, or planning his next vacation mid-case. Will be rich, so that’s a redeeming quality. Probably a chiller and will never understand why you’re freaking out. Will leave his clogs in the middle of the hallway.

Psychiatry

Will psychoanalyze you but pretend he’s not. Weird and quirky, but has done the work on himself to sort through his trauma. Likely a democrat (green flag). Weirdly unwilling to help you change a lightbulb. Definitely on an SSRI, will try to get you on an SSRI, believes SSRIs should be added to the water supply. Also takes board games too seriously.

Tier 3: No (Respectfully)

Neurosurgery

Extremely cocky, but he has to be. Personally, I wouldn’t want my brain surgeon riddled with self-doubt. Unfortunately, when it comes to dating, you’ll never be his priority. He’s actively choosing between sleep and seeing you, and will make sure you know where you stand. Brilliant, but structurally unavailable, so you’ll feel guilty for wanting attention.

Dermatology

Has a professional Instagram account dedicated to his accolades, one of which is his skincare routine—legitimately thinks he’s a skincare influencer. Maintains a vigorous moisturizing regimen and is kind of obsessed with himself. Your pores will always feel larger when you’re with him. Will shame you for not wearing sunscreen, despite exclusively posting sun-soaked selfies all over his IG.

Emergency Medicine

Thrives on chaos and constant stimulation. Blood permanently caffeinated due to his severe diet coke addiction. Carries rock climbing chalk and a bike helmet with him at all times. Eventually he’ll only work three days a week, which sounds appealing, until you realize the other four are reserved for skydiving and other activities currently spoon-feeding his short attention span.

Urology

Self-explanatory. Thinks d*** jokes are a personality. Knows too much about one thing.

Plastic Surgery

Honestly? I wouldn’t. Looks at other women’s bodies all day and knows what a perfectly symmetrical face looks like. On your first date, he’ll casually mention that he has Botox in his fridge and offer you some. If you do end up with him, congrats: you now have unlimited access to free procedures, in addition to lifelong insecurities you didn’t previously have.

Gynecology

This one is for the girls. I have questions.

Pathology, Radiology (anyone in the basement)

Highly intelligent but the dorkiest guy in the hospital. Chose this specialty to avoid human interaction, yet somehow has had several long-term relationships. Communicates through clinical statements. Bad at first impressions. Definitely a gamer.

If you’re a resident, you may be wondering if it’s possible for any specialty to make it into Tier 1. The answer is: no. The resident lifestyle is just too extreme to be compatible with fundamental relational behaviors, like spending time together.

So, ladies, date at your own risk. Or try again during fellowship.

—Cait xo

Subscribe now

*Disclaimer

I know residency is one of the most demanding jobs out there: you’re overworked, underpaid, chronically sleep deprived, and constantly responsible for patients’ wellbeing. Between long hours, extreme stress, and socialization limited to other medical professionals and patients you’ll never see again, it’s not exactly a setup that optimizes for emotional availability or the nurturing of connection.

As an outsider with a regular corporate job that requires only surface-level empathy and a healthy respect for deadlines, I have to assume that living perpetually in caretaker mode (especially in matters of life or death) reshapes how doctors approach their personal lives.

So, for legal reasons, please take this post as observational humor, and know that I truly admire all of your brilliance, hard work, and dedication to the care and keeping of humanity.

And a special thank you to the residents who gave me extra intel for this piece!

Consider this post an anthropological study of the oddly specific (yet universally recognizable) men you’ll date in Boston.

NESCAC Man

Kinda boring but fundamentally decent.

Rows with a Beacon Hill boat club and considers that a full personality. When you ask what they get up to socially, he’ll explain that they mostly just hang out naked in the communal shower. Most attracted to you when you’re wearing pearls (Freud would have questions). Owns Aesop exfoliating hand wash and a Diptyque candle that he bought himself.

First Date Location: Cocktail bars where the drinks are $24 [The Street Bar]

Birkenstock Intellectual

Overeducated but undersocialized.

He’ll think he’s better than you because he’s getting a PhD in quantum mechanics. He’ll take the booth without asking and tell you that his recent trip to Costa Rica lowkey healed him. At the end of the date, he’ll ask you who your favorite serial killer is, then insist on walking you home. You’ll decline. He’ll be wearing Birkenstocks, you’ll be wearing heeled boots. This will feel symbolic.

First Date Location: Natural wine bars where he mansplains the menu to you [Zuzu Petals]

Confederate Flag Old Navy Man

Deeply judgmental, morally questionable.

He’ll tell you women shouldn’t handle the family finances, then scoff when he finds out your jeans are from Old Navy. Eventually, you’ll learn he has a confederate flag hanging in his apartment. Later on, you’ll hear through the grapevine that he once had a girl spend the night and then lied to his friends about her breaking his toilet. This will feel depressingly on brand.

First Date Location: Anywhere overpriced [Lolita, specifically the Back Bay location]

Trust Fund ‘Quin House Man

Rich and deeply insecure.

He’ll flash his Rolex while ranking other people’s wealth like it’s a moral hierarchy. He’ll also insult other women savagely to your face, whilst insisting he’s actually very sweet. On the second date, he’ll gift you a framed painting of the restaurant where you had your first date—which will feel aggressive. He’ll be obsessed with the Patriots and won’t comprehend that you don’t care about football. He’ll also tell you he’s not into blondes, then proceed to date one immediately after you.

First Date Location: Members’ clubs only [he has a tab at The ‘Quin]

The International Love Bomber

All in, until he’s not.

He’s from a foreign country and has a tattoo of a sunset, which will convince you he’s emotionally deep. On date two, he’ll tell you he wants something serious. You’ll tell him it’s too soon, but against your better judgment, you’ll begin to open up. Things will progress, and 2.5 months later, you’ll ask him how he thinks things are going. He’ll end things, calmly, as if this were always the plan.

First Date Location: His go-to bar, the one he takes every girl to [Barcelona Wine Bar]

The Newton Narcissist

Ambitious on paper. Online in practice.

He’ll be everything you think you want. He’ll ask you to be his girlfriend really early, but he won’t really want to be a boyfriend. He’ll say he’s busy with his startup but actually spend all his time on Instagram. He’ll call this networking. You’ll become emotionally exhausted and get your first speeding ticket while spiraling over his inability to ever call.

First Date Location: A walk around the Charles, strictly at 6pm—he has an 8pm bedtime and is training for a marathon

Sick Boy

Supposedly ill.

He’ll delay your date four times over three weeks due to an unspecified illness. You’ll joke about asking for a doctor’s note. He will not provide one. You’ll end things. He’ll send you a voice note exaggerating his raspy voice to win you back. Then he’ll start texting exclusively in emojis. This will be your breaking point.

First Date Location: iMessage, specifically the Magic 8 Ball game he forced you to play

Sports Coat NJB

You fumble this one.

He’ll be the sweetest guy you’ve ever met and be ready to put a ring on it super early. Unfortunately, his signature look—sports coat, blue jeans, white button down with tiny rosettes—will throw you off. The way he scoops his hummus on the third date will seal his fate. You’ll cut it off prematurely. But you’ll think about him often.

First Date Location: Something genuinely thoughtful like a unique local event [MFA Late Nights]

Pickled Eggs MD

Clinically fascinating, romantically repellent.

He’ll insist he has the emotional and scheduling capacity to date, but he absolutely does not. He’ll wear crew socks with loafers and sport a really dense beard. You’ll laugh at the inclusion of pickled eggs on the menu, and he’ll un-ironically order them. When you ask for a residency story, he’ll tell you about the time a patient ate her own toe. You’ll never speak again.

First Date Location: Anywhere near the hospital, because he’s on call [Harvard Gardens, maybe Sevens]

*There are surprisingly no townies in this data set. Reader submissions are welcome in the comments.

More cities to come.

—Cait xo

Subscribe now

I was sitting on my couch with Nick when he told me I was lowkey tall for his family. We were four or five dates in and had just come back from kayaking on the Charles. I was excited about him; not only because he ticked my boxes but because being with him felt a little magical. We had sparks, and I thought we both felt them.

The mood shifted when he said it. Instantly, I was hyper-aware of my body: how much space I took up on the couch and how my height had turned into something he was evaluating—and maybe wasn’t into. The length of me was entirely out of my control yet suddenly seemed capable of putting the brakes on my burgeoning relationship

I didn’t know what to reply, because he wasn’t wrong. I’m 5’8”1, and I probably would tower over his mom and sisters, who he described as petite.

I can’t remember the first time I realized I was tall, or when I learned it was something to be self-conscious about. I just remember figuring out how to manage it: rounding my shoulders forward to make myself seem shorter, developing bad posture (which I’m still unlearning), and growing smaller in other ways to diminish the chance that I’d be noticed. My inherent visibility made me cautious of standing out, which is probably why I come off shy (another habit I’m trying to kick).

Then there was middle school, when my cross-country coach told me I was a big girl because I asked for a size S pair of shorts instead of an XS that literally wouldn’t have covered my butt. I wasn’t offended so much as confused. I was twelve and running miles a day. But the internal monologue ensued anyway: was I bigger than expected…or bigger than allowed?

Years later, a friend told me she listed herself as two inches taller on dating apps so she could filter for taller men2. I remember feeling a flash of anger that surprised me. She could toggle her height up and down on her own terms. My height, on the other hand, was fixed, and I’d been living inside it my whole life.

Taylor Swift would eventually put lyrics to that feeling: “Sometimes I feel like everybody is a sexy baby, and I’m a monster on the hill.”

Why Height Still Matters

Really what I’m getting at is that we move through a dating culture that likes its women small and its men tall.

I put my height on my dating profile to avoid disappointing men who are expecting someone shorter. Like a flag that says, “watch out, I’ll probably tower over you in heels.” At the same time, one of the first things my friends and I check on a guy’s profile is whether his height starts with 6’—proof that we’ve absorbed the same rules I’m about to claim to resent. This feels particularly pronounced in Boston, my current stomping grounds and a city full of men who swear they’re 5’10” (short kings, I salute you, and I know I’m bringing my own baggage to this party).

Since the dawn of time, we’ve been sold the idea that men should be taller than their girlfriends (RollingOut). It’s baked into pop culture, movies, and even children’s books. We notice when things line up, and when they don’t.

At the same time, femininity has always been tied to smallness (being quiet and dainty, while masculinity gets associated with largeness. This hierarchy shows up even in our language. He sweeps her off her feet. She falls for him. He stands above the rest. She melts.

As such, when a woman is tall, it disrupts the visual shorthand we’ve internalized, how a woman is meant to look (and act) next to a man.

So when Nick commented on my height, I don’t think he was being insecure or cruel. I think he was calibrating an internalized discomfort for how we’d be read as a couple—and what that visual might symbolize about our dynamic or his masculinity.

And I’m not immune to this conditioning either. When I saw wedding photos of the Mayor of Sausalito and her husband (clearly joyful and in love), the first thing I noticed was that she’s taller than him. I clocked it before I clocked their happiness, and I hate that I did that. The same happened when a video of Lucas Byrd, a 5’5” wrestler, and his 6’3” girlfriend, Ellie Holzman went viral. People are fascinated with them because their height difference doesn’t fit the script.

These reactions are revealing. They expose how deeply we’ve absorbed visual codes that assign meaning to something determined by circumstance (genes). And that has real consequences on who gets valued on the dating market, who lies about their height on apps, and how we all carry ourselves in the world.

From One Tall Girl to Another

Long story short, it didn’t work out with Nick—for reasons well beyond the height comment (lol). And I don’t know if the heteronormative cis dating scene will ever fully move past its visual norms. But I do know this: I’m no longer interested in slouching for anyone else’s comfort.

(All of that being said, if my future husband happens to come in a 6’3” package, I reserve the right to enjoy irony.)

If you’re a tall girl in the trenches with me, here’s what I have to say:

• Wear the high-heeled booties. You look great in them.

• Stop slouching to seem smaller. Hot girls have good posture. Put it on your 2026 bingo card.

• Don’t confuse height with confidence and be open to dating shorter men. In my experience, shorter men have better personalities than taller men who’ve coasted on being 6’5” and never had to develop social skills.

• If he’s weird about your height, that’s your answer. If you feel like you need to apologize for your body, he’s not the one.

• Some men like women. Others like women who make them feel big. Choose accordingly.

“In a world that tells women to shrink—physically, emotionally, and in their ambitions—choosing to take up space is an act of defiance” (TheThirdSpace).

Xoxo,

Cait

Subscribe now

There we were: five girls in our mid-twenties, dressed up for a night out in Boston’s South End. After pizza and ice cream at Picco, we headed over to Kartal followed by Beehive for drinks, dancing, and conversation.

Most of us were single at the time, and while meeting a guy wasn’t the primary goal of the evening, the idea hovered quietly in the background. Maybe this would be the night, and I’d finally get to call my mom and tell her that I met a NJB (or any NB) at the bar.

Time passed at our first stop. We nursed our drinks and stood in a circle, facing each other but scanning the room. We adjusted our Boston uniforms (ifkyk), reapplied our Summer Fridays’, and waited for the night to take a new turn. Around us, the bar was full of pairs and groups doing the same thing—strangers sharing the same perfectly curated evening.

Then we spotted them: a group of guys near the bar who seemed approachable. One of them was even over 6ft tall, which made him an undeniable Boston 10. We started shuffling towards them, mentally plotting how to talk to them in a natural, non-pre-planned kind of way.

But as we got close, we froze.

None of us wanted to start the conversation. One of my friends looked at me, and I looked back. An exchange that clearly communicated, well, I’m not doing it.

Eventually, Jocelyn, our one coupled friend, broke the ice. “Are you guys single?” she said. “You should meet my friends.”

Looking back, it’s both ironic and revealing that Jocelyn was the one willing to initiate. Maybe she felt like she had nothing to lose. Or maybe she was just being a good friend. Either way, what is clear is that none of us single girls wanted to be seen making the first move.

It felt too awkward and exposed. No one wanted to look desperate or, worse, rejected.

Sometimes I chalk it up to ‘traditional’ values, the idea that the man should make the first move. Other times, I blame shyness. But if I’m being honest, nonchalance was simply easier. It gave us an out—emotional armor that let us blame our not meeting a guy on the fact that we didn’t actually signal interest, or that men don’t approach anymore. That felt more natural than risking the embarrassment of putting ourselves out there.

So What’s Going on Here?

To me, our quiet avoidance feels like a feature of an urban gen-z dating culture that no longer holds the expectation nor the social muscles to mingle.

Now, I’m not saying that people never meet in person anymore. I’ve met friends at workout classes, book clubs, and coffee shops. But when it comes to dating, the unspoken rules around showing interest in public feel distinctly different. Why are we comfortable with very public dating profiles—which are literally screenshot-able and permanently archived—but the thought of openly mingling with strangers in person feels…awkward?

I’ve been chewing on this question for a while and have a few working hypotheses:

Rejection, But Make It Private: Dating apps offer asynchronous rejection and no witnesses—two qualities bars can’t compete with. It’s easier on the ego and emotionally safer to never see the rejection rather than to face it head on. Social psychology suggests that while apps make it easier to manage rejection sensitivity in the short term, they also risk catalyzing “excessive reliance” on online interaction over in-person vulnerability (PsyPost). In other words, apps have essentially given us the infrastructure to never face rejection again—so why would we?

All the Access, None of the Risk: The apps let us participate in the dating scene without fully committing. Almost everyone has an account, so having one doesn’t really mean anything. It doesn’t necessarily mean you’re trying (or failing) to date—you may be there for validation instead (more on ‘ego-scrolling’ here). Approaching someone in person, on the other hand, lays your cards out on the table immediately. And we’ve become too risk-averse for that kind of exposure.

Everything is Scheduled, Including Desire: Modern lives leave little room for mingling to happen naturally. We’ve concentrated the expectation of meeting someone into a handful of “going out” hours each week, creating an unnatural amount of pressure around them. Combined with the digital dating revolution and our increasingly overly-scheduled lives, our capacity for spontaneous interaction has become stunted. I know I’m always running between the office, Pilates, errands, and home—nose in my phone in the moments in between—leaving little room for chance encounters or fate to take its course.

So Many People, So Little Eye Contact: This question also points to what sociologists call the urban anonymity theory, the idea that high population density can actually foster isolation (ThinkDigest). Think about it: we’re surrounded by people constantly yet rarely initiate conversation. Even here, as I write this essay while visiting my parents in a large city in the American South, I’ve noticed a significant decline in “southern hospitality” versus a few years ago. Interaction happens instead in private spheres (home, work, online), while public spheres (even bars) fall victim to mutual indifference, the “implicit agreement to avoid engaging with one another” (Critical Sociology).

The Experiment

The real question isn’t just whether I’m willing to put my mingling muscles through boot camp. It’s whether we’re willing to recreate the conditions and the collective expectation for mingling (romantic, or otherwise) to happen at all.

I don’t have the answers yet. But I’m 27 years old and ready to get over myself and have more “messy, glorious, chaotic” fun. So, consider me a test subject—I’m officially conducting an experiment on what it’s like learn to mingle again.

We’ve already covered Part 1: the diagnosis. Part 2 will be me, gone mingling (rejection therapy and all).

Wish me luck.

Xoxo,
Cait

Subscribe now

I’m here because I wanted to start writing again. And every time I did, I kept coming back to dating. So, I’m following that thread and writing my way through it.

My credentials include a near-lifetime of singledom and enough dating stories to qualify as both informed and exhausted.

After experiencing my first heartbreak and a few years in the trenches, I’ve started recalibrating my dating approach to something that feels like me again.

Subscribe now

Beyond my own experience, I also have a broader curiosity for dating, connection, and compatibility. I’ve studied them formally (s/o to my college seminar on Dating in the Modern Age), watched them play out on reality TV (is anybody else obsessed with Love on the Spectrum?), and observed them closely across friends’ lives.

I’m interested in dating not just as a lived experience, but as a cultural system, shaped by unspoken rules, negotiated vibes, and digital conditions.

My hope is that this newsletter helps us make sense of modern dating culture, keep our standards intact, and trust the slow burn (both in love and in life).

And if I’m being honest, I’m writing this for myself too. Because I still believe a significant partnership is waiting for me. And unfortunately (or maybe fortunately), that requires me to keep dating.

Here’s what you’ll find here:

• Notes from the inside: reflections on dating, independence, and emotional recalibration

• The dating scene: opinions on the places we meet, flirt, and miscommunicate

• Collective conversations: essays on dating culture, patterns, and differing perspectives (yes, I’m finally putting my Sociology degree to good use)

The Slow Burn starts now, every Wednesday.

Xoxo,
Cait

Subscribe now