The Playdate Theory Just Explained Why “Good on Paper” Guys Always Make Me Yawn

They met at a candlelit cocktail bar in the West Village—one of those velvet-lined places that exist mostly for TikTok. She was a writer, Prada messenger bag slung casually over her shoulder. He was a consultant, fresh out of Midtown, Patagonia vest layered over a crisp white button-down. Their date was set for 7:30, and by 7:52, they were deep in a discussion about timelines—his lease, her career trajectory, whether either of them was “open to kids.” It wasn’t a bad conversation, per se. It just was… productive. The kind where no one (really) laughs. 

When she left two hours and two cocktails later, she couldn’t decide if she felt satisfied or vaguely depressed. Was she supposed to be relieved that he was eager to father three kids? Grateful that he asked follow-up questions about her writing? Mostly, it felt like a second-round interview for a position she wasn't even sure she wanted.

Cut to a few weeks later: different bar, drastically different vibe. This guy arrived twenty minutes late, charmingly frazzled and apologizing as if he'd just blown the final round of Jeopardy!. The maître d’ couldn’t locate his reservation, and they ended up wedged into a booth between the bathroom and a shrieking birthday dinner two tables over.

And yet—it was fun.

There were no pre-rehearsed talking points—no clinical inquiries about climbing career ladders or what each other’s love languages were. Instead, they teased each other mercilessly. He dubbed her “the female Hank Moody,” and she mocked him for living with monks after college. They swapped stories, stacked jokes and laughed until their cheeks hurt. And somewhere between her third martini and the house lights flipping on at 2 a.m., she realized: She was having more fun on this date than she’d had in months.

Because it didn’t feel like a first date. It felt like a playdate.

The scenes above are pulled from my own life. One date had me nodding politely through an excruciatingly banal chat about Roth IRAs. The other was a kind of chemistry that made me forget where my phone is. And it was after that second encounter—the one with improvised seating and monk jokes—that I coined what I'm calling The Playdate Theory. The premise is simple: if you're not playing on a first date, you're not connecting.

This realization crystallized while reading David Brooks’ How to Know a Person. In it, he writes, “When we're at play, we’re our most authentic selves.” Because play isn’t just something we do as kids—it’s foundational to our deepest adult connections. “This is where trust is built,” he explains. “Where we take social risks, and where the real self emerges.” Yet, when it comes to dating—especially once we're past our mid-20s—playfulness seems to vanish from our vocabularies.

Right around the time we decide we're ready for “something serious,” dating starts feeling less like play and more like a performance review. I’ve watched it happen to almost every woman I know—and more recently, guy friends who are worried they’ll be the weird single uncle at family BBQs. We show up dressed for the part. We meticulously run through talking points. We measure alignment on everything from family planning to hygiene habits. But we’re not asking, Do I feel good around this person? Instead, it’s: Are they ready? Are they worth it? Am I wasting my time?

Playdate Theory offers a shift in perspective. According to Brooks, playfulness invites openness, spontaneity and connection—and it doesn’t need to be dramatic. (In fact, it’s supposed to be subtle.) Because when we’re at play, we reveal a layer of “spontaneous communication” that’s more illuminating than any scripted backstory. This author even compares it to how new parents bond with their babies. “Though we knew each other so well,” he writes of his infant son, “we had never had a conversation.” Their bond was built simply by being together, not by analyzing each other.

Think about it: The best relationships aren’t born out of certain clarity. And I’m not just talking about romantic connections—it can be any kind of bond, whether that’s with a friend or a first date. Anything that feels genuine starts with chaos—an unfiltered conversation, a casual poke of fun, a mishap that leads to a memory you couldn’t possibly anticipate. (Read: Craic Test). It’s like the basketball game Brooks describes in his book: The players may never talk about anything “deep,” but they would lay down their lives for each other. Not because they dissect their attachment styles mid-drill, but because they pass the ball, miss shots, talk trash, and keep showing up. That’s intimacy—trust built through action rather than analysis.

And it's what my Playdate Theory aims to prove: that true intimacy isn’t something you can manufacture. Real chemistry emerges from moments you never scripted—spontaneous interactions where your guard slips just enough to reveal something authentic. Yet, after years of writing about dating trends, I’ve noticed a concerning theme: we use carefully curated checklists—our relationship “must-haves”—as armor against rejection. Instead of leaning into connection, we politely nod our way through endless rounds of evaluation. Withholding our true selves until it feels safe; until we're certain there’s no risk. But what’s ironic is that it's these protective standards that keep us from building the intimacy we so deeply crave. Because intimacy doesn’t grow in safety—it grows in play.

In reality, having fun and finding your person aren’t mutually exclusive—they’re one and the same. And if you let go of what you think you want on paper, you might discover qualities you didn't even know you were looking for: a refreshingly dry sense of humor, unexpected thoughtfulness, or the ease of someone who makes two hours feel like twenty minutes. That’s the magic of play—once you stop worrying about what’s supposed to feel right, you start noticing what actually does.

So, before your next date, try flipping the script. Treat it like a playdate your mom arranged back in second grade. You want to show up assuming you're there to have fun, and remember you never have to see them again if it goes sideways. Best-case scenario? You find someone you can’t wait to see again—setting yourself up not just for another great date but for a lifetime of playdates. 

After all, committing to someone's cringe-worthy dad jokes—just because they ticked the 'wants to be a dad' box—isn't intimacy. It's a lifetime spent on a playdate you wish you could leave.