I Hate to Put My Guy Friends on Blast, But This Is The Dating Mistake They Make on Repeat

It’s a Sunday morning at Bubby’s in Tribeca. The table is littered with half-eaten eggs, lipgloss-stained coffee cups and a certain Sex and The City energy that can only come from four women dissecting their dating lives.

Me: “Addy, didn’t you go out with Maryland guy on Thursday?”

Adrianna: “Yep… heard about his entire fantasy football lineup, his gluten allergy and how much he spent on his Rolex. Ask me if he knows what I do for a living.”

Grace: “Guys don’t ask questions anymore. It’s a thing. Tinx just made a TikTok about it.”

Brielle: “I saw that! And I was thinking, like, even if the guy does ask a question, there’s no follow-up. I went on a date last week where I could’ve said I’m an astronaut—his response still would've been, ‘Oh, that’s cool.’”

Long after brunch, I kept returning to the conversation in my head. So I decided to run it by my guy friends. Their responses were uniform: “Of course I ask questions on a first date.” Yet, when I pressed, I noticed a pattern. They could list off their typical inquiries: “What do you do?” “Where are you from?” “Have any siblings?” But when I asked if the responses had led to anything substantive—if they had sparked something interesting with the person sitting across from them—there was a long pause.

And that’s when it hit me. The biggest mistake 20-something men are making on first dates isn’t about the questions they’re asking (or failing to ask). It’s that they’re struggling to create meaningful interactions that resonate with women.

Before we get into dating, I think it would be helpful to start in the world of male friendships. As Andrew Licout parodied in the TikTok above, men breeze past major life events—divorce, rehab or losing their house to a literal fire—while still making the seamless switch to, “Wanna grab a beer?” And the comment section on this video indicates that it’s not an exaggerated bit; this is what it looks like when two guys catch up. “They listen, and they don’t judge,” one person writes. “No details, no questions, just vibes,” another chimes in. It goes to show that for men, a conversation without follow-ups isn’t just normal—it’s expected. Their friendships aren’t built on “Tell me your deepest frustrations over brunch.” Instead, the unspoken rule is: I’ll share what I feel like sharing. If I don’t, we’re not going to make a thing of it. 

In fact, there are multiple studies on gendered communication that back this up. Published in the Journal of Applied Communication Research, a study entitled, “In a Different Mode: Masculine Styles of Communicating Closeness” by Julia Wood and Christopher Inman found that men bond through ‘doing’ rather than talking—watching the game, playing poker, scrolling their phones in silence. A separate 1995 study published in Sex Roles, also confirmed what (most of us) already know: men engage in far less verbal self-disclosure. Their conversations tend to focus on logistics—quick updates with just enough surface-level banter to keep things moving. It’s why, when a guy’s best friend gets dumped, he’s not saying, “How are you really feeling?” He’s more likely to say, “Damn, that sucks. Let’s go to the bar and forget about her.”

Yet, while men bond by doing, women bond by talking—and by talking I mean analyzing, unpacking, deconstructing and revisiting. When something happens—a weird text from a guy, a passive-aggressive comment from a coworker—we don’t just state the fact. We workshop it. We gather perspectives, dissect the subtext and leave no emotional stone unturned.

Again, the research supports this. Wood and Inman found that men engage in “side-by-side” friendships (through activities), whereas women form “face-to-face” friendships (through emotional exchange). Women don’t just ask what happened—they ask how it made you feel and why it mattered. Likewise, Leaper’s study found that women engage in self-disclosure at a much higher level than men. When a friend tells a story, a woman is more likely to probe deeper: “What do you think caused that reaction?” It’s not just a conversation—it’s an excavation.

So now, we have a man and a woman on their first date. She’s expecting an emotional exchange; he’s expecting to keep the conversation moving. And therein lies the impasse I’m seeing. Again, women build their bonds through the why, the how and the who: “Why did you choose that career?” “Who is your celebrity crush?” We crave dialogue that makes us pause, reflect and maybe even learn something about ourselves. Men, on the other hand, tend to lean on the what: “What’s your gym routine?” “What kind of music do you like?” To him, he’s ‘doing the work’ of conversation. But to her, it feels like he’s checking boxes on an intake form.

And so, when women complain about men not asking questions, they don’t actually mean ‘men aren’t asking any questions’ (well, for the most part). What they mean to say is that men aren’t asking the right follow-up questions. Because when we share something on a first date, we’re not just responding to a question—we’re offering a thread to pull on. The problem is, most men don’t know how to pull it.

Of course, when I explained this to my guy friends, they were exasperated: Then what the hell are women looking for? I realized there’s a three-step formula women use that might seem less obvious to men: ask, *listen,* adjust follow-up accordingly. Here are some examples I gave them:

She says: “I studied art history in college but ended up working in advertising.”
He hears: “Cool, she works in advertising.”
She wants him to ask: “Wait, what made you switch from art to advertising?”

She says: “I just got back from a trip to Portugal.”
He hears: “Cool, she likes traveling.”
She wants him to ask: “Why Portugal as a destination? What drew you there?”

She says: “I ran a half-marathon last year, but I didn’t train for it at all.”
He hears: “Cool, she likes running.”
She wants him to ask: “Wait—why didn’t you train? Were you testing yourself? Were you afraid to fail?”

See the difference? It’s not necessarily about asking the right questions—it’s about listening to answers and engaging with what’s being said. To that end, I was recently reading a great book by David Brooks, who pointed out that children ask the most revealing (and often inappropriate) questions—ones adults have been socially conditioned to avoid. A child will ask, “Why is your face like that?” or “Why are you sad?” because they haven’t yet learned the unwritten rules of polite conversation. And while I’m not suggesting you interrogate your date like a nosy five-year-old, there’s something to be learned from their approach. They don’t just accept an answer at face value—they instinctively dig deeper. And if you ever get stuck, the simplest hack is: “Tell me more about that.” Works every time.

All of that being said, I think it’s worth pointing out that 20-something men aren’t the only ones struggling here—women are too. The only difference is that we’ve learned how to disguise it better. When faced with an awkward silence, women are more likely to fill the gap, pivot the conversation or double down on their own storytelling. We hate the discomfort of a stalled interaction, so we compensate. But that doesn’t mean we’re always asking the right questions—or follow-ups—either. In a lot of ways, we’ve also forgotten how to truly engage with someone outside of our own perspectives.

Perhaps that’s the real issue here. More and more, I’m realizing we’re a generation shaped by algorithms—ones that feed us exactly what we want to see, validate what we already think and rarely challenge us to step into someone else’s world. But real conversation isn’t curated; it’s unpredictable. And the best ones require a level of curiosity that goes beyond our own pre-existing interests. 

Nevertheless, if you’re a 20-something guy, my best advice is to ditch the generic, box-checking questions and put your energy toward engaging with her responses. And if you’re a 20-something girl? It’s also worth acknowledging when he’s trying—give the conversation a chance to unfold, instead of carrying it entirely on your own.