Dating, Plato once said, is like enlisting in a gangbang of rejection, lizard-tongue make-outs, and 2 am doom-swiping. It’s vulnerable, expensive, and time-consuming. Sure, when dating is great, it’s really great (love, sexual enlightenment, etc.), but when it’s bad it can feel oppressive—like you’re on an endless series of job interviews, applying for the position of “everything I want in life.” No pressure.
I spent the first half of my 30s in a long-term relationship. Having now been single for over a year, a friend recently asked me the seemingly innocuous question: So, what are you looking for? “Well...” I said, taking a deep, anticipatory breath. “I’m looking for a guy who’s ready to commit, who is handsome, kind, successful, fit, creative, funny, in therapy, taller than me, can fix things around the house, who wants a family but ideally doesn’t have kids yet, and who’s between the ages of 36 and 43—ya know, give or take a year.” My friend looked at me like he feared for my life. “So, you’re basically trying to hit the world’s smallest target?” he asked.
“No,” I told him. “This is just dating at 37.”
Obviously, looking for love at any age has its issues. But for those of us who are allegedly fully fledged adults, I want to know: Does dating get harder after 30?
To preface this: I’ve always been a fan of dating. I love getting dressed up, sitting at a bar with a dirty martini, and getting to know someone new. I love the tension of, Will we kiss? Who will “accidentally” brush the other person’s leg first? Will I go back to his place to find the fridge stocked with more than just IPAs and mushroom chocolates? (The dream!) However, dating after 30 does bring new challenges. Namely, the dating pool is dwindling, your eggs are expiring, and you’re inching closer to death—plus, a bunch of other tired clichés that, annoyingly, are pretty spot on.
My friend Lauren Garroni recently got into a great relationship after years of being jaded about dating. She’s 35 and one half of the much-loved Every Outfit fashion podcast. She also has a lot of opinions about modern courtship. “Being on dating apps was the longest unpaid internship of my life,” Lauren told me with a dramatic eye roll. “When you’re single in your 30s, all your friends in relationships are like, ‘You have to give people a chance or you’ll never meet anyone!’ I went out with so many guys that I wasn’t excited about because I felt like I ‘should.’ I don’t even want to know how many hours of my life I’ve wasted on bad dates.”
While my list of dating criteria gets longer with age (see: paragraph two), Lauren says her years of dating fatigue actually stripped her standards to the bare essentials. She lamented, “Once I hit my mid-30s, my checklist shrank down to: Are you a psycho? Do you have a job? And have you asked me a single question on this date?”
That last one resonated with me. The number of dates I’ve been on where the guy didn’t ask me anything about myself is actually wild. I now play a game with myself where, if I’ve spent 45 minutes essentially interviewing a guy with no reciprocal curiosity, I’ll start leaving some dead air in the conversation to see if he fills it with a question. Turns out, an awkward silence is an excellent opportunity to continue monologuing about yourself.
Somewhat reassuringly, though, it’s not only women who feel the pressure of age. My friend Jake recently turned 40. He’s handsome, talented, and undeniably charming, but he’s also—in his words—“disastrous, financially unstable, and alone.” Recently, for the first time in his life, he’s found himself dating women considerably younger than he is—and it can sometimes feel depressing.
“I always assumed I’d be married with kids by 40,” Jake told me, looking like a hot cliché in overalls covered in motor oil. “Now I keep asking myself: Am I dating younger women because it’s playful, or something my body is biologically drawn to? Or is it because if someone 29 tells me I’m a mess, I can shrug it off, like, What do you know? Call me in a decade. When that sentiment comes from someone my age, it cuts a lot deeper. Maybe I’m just scared of being in a relationship where there’s more accountability.”
I get it. Being exposed in that way isn’t thrilling—especially if you re middle-aged and still threatening to move to Berlin. And as we get older, everything seems more consequential. I keep finding myself thinking, Oh, God, he wears those little no-show socks, or, he quotes Jordan Peterson, or, he has a weird dick—can I deal with this for the rest of my life?! At the same time, showing up to a date like: “Are you the one who’s going to impregnate me, because time is running out?!” is not creating the most fuckable energy.
Now, clearly the world is full of wonderful men who aren’t couch-surfing narcissists—or, there are at least enough to go around. The question is: Where are they hiding? Lauren told me, “For decades, single women have been asking themselves: Where are all the great single men? And my working theory is they’re in bad relationships. The intelligent, would-be emotionally available men aren’t single, because they’re too invested to leave their failing relationships.”
“So are you saying the way to find a man in your 30s is to break up a marriage?” I asked her.
“I didn’t say that,” she replied sternly. “I’m just saying that, as anyone who has grown a business knows, the real talent is always booked and busy. And how do smart businesspeople recruit great workers? They poach them.”
No comment.
Personally, my current romantic strategy is a little different. My take is, you have to get a man on the second wave—he’s already done the big relationship, so he’s broken in, house trained, and you know he can commit. Then you swoop in about a year post-break-up, once he’s ready for round two. This, I’m convinced, is the platonic dating ideal of the 35-plus set. I’ve coined this approach “Second Wave Feminism”™.
Another advantage to dating after 30 is that, as you get older, you become less of an idiot. In your 20s you have more time to waste, and you also vaguely hate yourself, which is a dangerous combo. The amount of psychotic behavior I put up with in my 20s—and that I projected myself—is actually embarrassing. Like, “You’re emotionally unavailable, your sheets are stained with another girl’s period blood, and you exclusively text me after 1 am? Sign me up!” It wasn’t cute.
Now, my price of admission is a lot higher, even for casual sex. Shockingly, I now care if someone is, like, a good person? If it’s clearly not working, I end it after two dates—rather than two years. Age makes you more discerning in a way that’s genuinely exciting. You get to choose a partner from a place of knowing yourself. Today, I find myself attracted to qualities that, a decade ago, were basically invisible to me. Like recently, I was at a barbecue and this guy was in the kitchen, just quietly cleaning up to help out the host, and I swear I’ve never been more turned on.
And sure, it sometimes works out marvelously for high school sweethearts. And I should probably be more flexible about my never-ending romantic checklist. But I feel genuinely lucky that I get to choose a partner at a time when I get wet for a man holding a sponge, rather than a sociopath in the right shoes whose mixtape got a write-up in Pitchfork.
