Men Are Trapped Inside Boys
I read a story in VICE this week about why Gen Z and Millennial men stopped approaching women in public, and my first reaction wasn’t sympathy. It was déjà vu.
The story: a 28-year-old cybersecurity analyst in Manhattan says he wants a relationship but rarely approaches anyone in real life, because he’s afraid of making someone uncomfortable.
A 24-year-old actor says he’s done trying entirely, after enough public rejection that the math stopped making sense to him. A survey found 44% of single men admit that fear of being labelled creepy makes them less likely to say hello to a stranger. Meanwhile, 77% of women in their 20s and 68% of women in their 30s said, in the same survey, that they wish men would approach them more.
So: everybody wants the same thing, and nobody’s doing it.
Welcome to the most expensive game of chicken in the history of dating.
I’m not here to pile on. I’ve got two teenage daughters, so I hear this from their side of the gender conversation — the guys they like text for three weeks and never ask them anywhere, the group chats that never resolve into an actual date, the low hum of “does he like me or does he just like texting me” that seems to define an entire generation’s early dating life.
I get why the guys are doing it.
They’ve been marinating since birth in stories about men who misjudged a moment and paid for it publicly, permanently, and disproportionately. They’re not wrong that the risk is real. They’re just wrong about which risk is bigger.
Here’s what nobody’s telling these guys: opting out isn’t neutral. It feels like caution, but it’s actually its own kind of failure — just a quieter one, with no witnesses and no viral clip.
When I was in my 20s, “approach anxiety” wasn’t a term anyone used, mostly because you didn’t get the option to opt out of human contact and still have a social life. If you wanted to meet someone, you walked over.
You said something, ideally something that wasn’t “nice haircut” delivered while blocking a hallway. You risked the flat stare, the polite deflection, the friend who materialised out of nowhere to run interference. It stung. You did it again the next weekend anyway, because the alternative was staying home, and staying home didn’t get you a boyfriend.
Was some of that approach culture bad? Extremely.
I have stories, and so does every woman I know. We were cornered at parties by men who couldn’t read a single social cue and wouldn’t have cared if they could. Nobody’s asking to bring back 1994 unedited.
The instinct to be more careful, more aware, more conscious of consent and comfort — that part is genuinely good, and I’d fight anyone who tried to walk it back.
But somewhere between “read the room” and “never enter the room,” a whole generation of men found an exit and took it. And what they landed on isn’t more respectful.
It’s just safer for them — and lonelier for everyone.
But the thing is: they’re getting the failure math all wrong. Rejection was never the actual disaster. A “no thanks” from a stranger at a coffee shop costs you thirty seconds of embarrassment and nothing else. It doesn’t follow you home. It doesn’t show up on anyone’s phone. It’s forgotten by both people within the hour.
What’s not forgotten, apparently, is the fear of becoming a story. The guy who got filmed, screenshot, dragged online for fifteen seconds of secondhand cringe is a real phenomenon and I’m not dismissing it. But it’s also an incredibly rare outcome being treated like a baseline expectation.
Most women who get approached politely and then declined don’t pull out a phone. Most of them just say “I’m good, thanks” and move on with their day, the same as they’d hope a man would do with them.
The dating coach quoted in the VICE article put it about as cleanly as it can be put: “Women aren’t saying, ‘Don’t come talk to us.’ They’re saying, ‘Don’t objectify, harass or disrespect us.’” That’s a genuinely narrow, learnable line — not a minefield.
But if you’ve spent your entire adolescence being told the line is invisible and the penalty for missing it is public humiliation, of course you’d rather not walk it at all.
I think GenX parents did something well-intentioned here that backfired a little, collectively. A lot of us raised sons to be aware, to ask first, to never make anyone uncomfortable, to think hard before they acted. All correct.
What a lot of us maybe didn’t do enough of is teach them that rejection is survivable, boring even, and that a little bit of risk is the entry fee for any relationship worth having.
We handed them the caution without the confidence to go with it, and caution without confidence doesn’t produce respectful men. It produces men who stay home.
I raised daughters, not sons, so I watched this play out from the other side of the table. A lot of us raised our girls to speak up, to make the first move themselves, to not sit around waiting to be chosen. Good. Necessary.
Except now you’ve got a generation of women who were told to go get what they want, meeting a generation of men who were told not to want anything out loud, and the two of them are just… waiting. Politely. Forever. On apps that both sides agree they hate.
The apps didn’t fix this. They just hid it.
Because one thing everyone conveniently forgets when they talk about dating apps replacing real-life approaches: the apps didn’t solve approach anxiety. They just moved it somewhere you can’t see it happening.
Swiping isn’t brave. Swiping is the least risky possible version of interest — a tiny anonymous vote that costs you nothing and reveals nothing about you until someone else has already said yes first. That’s like meeting with an escape hatch, dressed up as innovation, and an entire generation walked through it gratefully.
The result is a dating culture where both sides are technically trying and neither side is actually risking anything. Men wait for a match to remove the uncertainty before they’ll say a word.
Women wait for men to message first, because after enough bad experiences, initiating with a stranger who can’t be vetted feels like its own kind of exposure.
Everyone’s optimising for safety, and the byproduct of a whole culture optimising for safety is a whole culture that’s lonelier than it wants to admit.
I’d also gently point out that this isn’t just a heterosexual man’s problem, even though the coverage always frames it that way. It’s a symptom of something broader — a generation raised inside constant surveillance, where every interaction is a potential clip, and the rational response to that is to interact less.
Gen Z inherited an environment where caution is the only move that never blows up on you publicly, and then they got blamed for playing it.
GenX knows rejection isn’t a life sentence, because we survived a lot of it and turned out fine, occasionally annoyed, but fine, whatever.
We know a moment of embarrassment beats a decade of wondering. And we know that “I don’t want to make anyone uncomfortable” is a fine instinct right up until it becomes a permanent excuse for never finding out what could’ve happened if you’d just said hello.
The line between respectful and invisible is thinner than either generation wants to admit.
Somebody’s going to have to walk up to somebody.
It might as well be either of you.
-Dana Dubois
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