For a generation raised on dating apps, social awareness, and endless discourse about consent, a strange thing has happened. A lot of young men have stopped approaching women altogether. Not because they don’t want to date. Not because they lack interest. Because they’re scared of getting it wrong.
The New York Post recently reported on what it calls “approach anxiety” among Gen Z and millennial men, and the stories feel familiar. Ryan Kessler, a 28-year-old cybersecurity analyst in Manhattan, told the publication that he wants a relationship, but rarely approaches women in public because he worries about making someone uncomfortable. “I never want to make the other person feel uncomfortable, and I want to be respectful,” he said, explaining that he usually chooses caution over connection.
That hesitation is widespread. A 2025 survey cited in the article found that 44 percent of single men said fear of being labeled “creepy” makes them less likely to initiate contact. This isn’t about confidence in the traditional sense. It’s about social risk. Being filmed. Being screenshotted. Becoming a punchline online for misreading a moment.
Why Gen Z and Millennial Men Have Stopped Making the First Move
What complicates things further is that many women say they actually want to be approached. The same report found that 77 percent of women ages 18 to 30 hoped men would do it more often, along with 68 percent of women in their 30s. In a viral clip, a woman named Liv said she respects men who politely make the effort, calling it admirable “in this day and age.”
Women aren’t imagining the risk here. Most of us have learned, often early, that a polite no doesn’t always close the interaction. Viv, a lifestyle creator, described experiences of being followed and physically touched after declining advances. You carry those memories into every new encounter, even the harmless ones.
Dating coach Connell Barrett told the Post that respect doesn’t mean disappearing. “Women aren’t saying, ‘Don’t come talk to us,’” he said. “They’re saying, ‘Don’t objectify, harass or disrespect us.’” That’s a narrow line, and many men don’t trust themselves to walk it.
Some have opted out completely. Grant Greenly, a 24-year-old actor and model, told the Post he’s done approaching women after repeated rejections and one particularly cruel response. “Approaching women today isn’t worth the hassle,” he said, citing fear of public embarrassment and online ridicule.
The result is a dating culture stuck in limbo. Men wait. Women wait. Apps pick up the slack, even though almost everyone claims to hate them. Equality gets invoked, but no one agrees on what it looks like in practice.
This isn’t nostalgia for bad pickup lines or louder men. It’s a generation trying to do the right thing, unsure where the line is, and lonelier because of it. Wanting connection hasn’t changed. The rules around how to reach for it just feel harder to read than ever.
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