Issue #99: How dating has changed in our 30s

What we care about, what we don't, and the first-date questions we now ask...

, and

Apr 17, 2025

Interview by

and

The other day, I (Aliza) was catching up with a friend, who’s newly single at 34. “Dating in my thirties feels completely different,” she told me. “My questions have changed from wanting to know where someone went to college to how they see the future — and that’s on date one!” It made me think about how the questions we ask potential partners evolve as we get older and our priorities shift.

I was curious, so I asked several women about the questions they ask on dates now versus in their twenties. Here’s what they shared...

Your friendships are often a reflection of who you are:

“In my twenties, I was most interested in fun. Can we laugh? While that’s still vital, I’ve learned that fun doesn’t hold a relationship together. I’m more careful in my thirties. I want to know about your politics and where you stand on social issues. I want to know what your friends are like, because they’re often a reflection of what kind of person you are.”

- Madeleine Rebouche

Life comes down to the in-between, everyday moments:

“The most important questions I ask today are: ‘What are your values?’ and ‘What does a good life look like to you?’ In the past, I used to ask more about the other person's interests, taste in music and books — surface-level things. But I’ve realized that while of course it’s important to have fun with my partner, we don't need to have every hobby, band, or sport in common. So much of what life is truly about comes down to the in-between, everyday moments: What would it feel like to come home to each other every day? Do you make me feel heard and seen? Do we bring out the best in one another?”

firefly mizera

I care less about the “resume” details:

“In my twenties, I approached dates like an interview, focusing on information I could get from a resume: where they went to school, their job, their hometown, etc. As I’ve moved into my thirties, I care less about those details. Instead, I’m curious about whether they find meaning in their work, or what it was like growing up in their hometown and how those experiences have shaped them.”

- Zoya Q.

First dates can (still) feel more like a game of Twenty Questions:

“I’ll be honest: I didn’t do a ton of dating in my twenties. I didn’t feel great in my body, or great about myself, so I didn't put myself out there as much. In my thirties, I hit my stride — and I found myself navigating a New York City dating scene that was… rough. New Yorkers are ambitious. It’s something I love about my city! But it often results in first dates that feel more like a game of Twenty Questions: So, where in the city do you live? What do you do for work? What do you like to do on the weekends? All of these questions are fine and good, but they often don’t get you to the heart of a person. A while back, a good friend of mine told me she’d started asking dates to tell her about their best friend(s). People’s friendships tell you so much about them — how they navigate relationships, whether they can commit, what they value. It’s a really nice way to get to know how and with whom someone chooses to spend their time.”

Sarah Jacobson

, author of
big feelings

I don’t have to put on a facade that I’m an amazing catch:

“In my thirties, I’m not afraid to ask about the hard times. By this point, most of us have faced an unexpected curve ball — the death of a loved one, a layoff — those moments where you get earthquaked out of every stable thing in your life. I feel less like I have to put on a facade that I am an amazing catch… and more interested in genuine connection.”

Gabriella Singh

, author of
Figuring It Out

Politically, we at least need to be on the same page:

“Ten years ago, I wasn’t politically engaged. While I always wanted to connect with men who had similar morals and values, I never brought up politics on dates. Now, I won’t swipe right on someone who lists themselves as a conservative — and even ‘not political’ will make me pause. There’s no way I could fall in love with someone who’s pro-life and doesn’t think children should have a free meal at school if they can’t afford it. I’m well-aware that no one will see eye to eye with me on everything… but we at least need to be on the same page.”

- Jessica Camerata, author of

an indigo day

Trusting myself has allowed me to have less of “a list”:

“When I was younger, I was very eager to please and very desperately wanted to be liked. Now, I’m much more confident and care about how we naturally fit into each other’s lives rather than how I can mold myself into his. Day-to-day lifestyle factors are way more important than I used to believe — things like when we go to bed, our energy levels, how we want to spend vacations and down time. These things don’t have to be the same, but I look for compatibility. Beyond that, I ask more open-ended questions to get a sense of who someone is, their morals, beliefs, things like that. I think feeling comfortable with and trusting myself has allowed me to have less of ‘a list’ and feel confident walking away when I know someone would be better suited to another person.”

Hannah Stella

, author of
moxie

I ask where they want to end up:

“In my twenties, I’d ask where they worked or where they went to college or what their family dynamics looked like. I wanted to understand how I would fit into someone else’s world, as I had lost my own footing. (My mom died when I was twenty-two.)

In my thirties, I’ve learned what feels more crucial to me is where the person’s life is going. I have no regrets about wearing my heart on my sleeve and leading with grief when I was younger. But now that I feel more settled in myself, I ask where they want to end up, how they want to spend their money and time, and what celebrations look like to them.”

Lily Sullivan

, author of
Love and Other Rugs

Whether we wanted kids came up in hour two:

“I’ve found myself (or my date) asking, ‘What are you looking for?’ far sooner than my 23-year-old self would have felt comfortable with (I’m 32). On my last first date, whether we wanted kids came up during hour two (a personal record!) I’ve also found that the old and familiar questions have new meaning. Questions about exes have a different motive. Previously, I might have found myself comparing myself to them. Now, I’m more curious about conflict resolution style. Ten years ago, my date’s insecurities were likely a turn-off. Now I almost like them; they’re proof they’re a real and vulnerable person.”

- Georgia (name has been changed)

I’m free to be curious about who they are and how our dynamic feels:

“I ask fewer ‘qualifying’ questions. I chose to have a baby (now almost two years old!) with my best friend and have built a full and complete life without a romantic partner. Romance is something that I deeply yearn for — but it’s no longer the foundation I’m looking to build my life upon. I feel no pressure to ask my date any questions that might subtly get at: their willingness to share domestic labor, our financial compatibility, their fitness as a potential parent, etc. I’ve got all that stuff covered already. Instead, I’m free to be curious about who they are and how our dynamic feels. Don't get me wrong, I still feel plenty of pressure, but it comes from trying to figure out if this person is willing to see romance fitting in their life in a less conventional way.”

Amrita Vijay

, co-author of

Emergency Contacts

Thank you so much to these wonderful women for sharing their experiences.

Now we’d love to hear from you — how have the questions you ask on dates changed since your twenties?

Issue #99: How dating has changed in our 30s

What we care about, what we don't, and the first-date questions we now ask...

Discussion about this post