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Like many American men of his generation, Ryan Kessler, 28, is terrified of talking to women.
But it’s not a lack of smarts or swag that makes the single Manhattanite hesitant to approach women out in the wild; it’s the fear of being mistaken as a toxically macho, bone-headed creep.
Kessler told The Post that when trying to win over a potential love interest, the last thing he wants is to be considered a jerk who makes ladies cringe rather than swoon with a clumsy pickup line and unwelcome advances.
“I never want to make the other person feel uncomfortable, and l want to be respectful,” the cybersecurity analyst told The Post. “Some girls don’t want to be approached at all. So, I’m always trying to err on the side of caution.”
As a result, Kessler said these days his “interactions with women are very few and far between,” although he is on the hunt for his happily ever after. “I want to find ‘the one.”
Kessler considers himself a good guy but still has difficulty, at times, to muster up the courage to approach New York women at coffee shops, bookstores or even subway platforms.
“I don’t want to bother them,” the wannabe loverboy said, conceding that he’s not as timid when it comes to making the first move on dating apps, like Bumble or Hinge. Singles are on there to be digitally approached, yet “a lot of the time, in person, [women] are not there to be approached, so it’s kind of odd,” the 28-year-old pointed out.
Not wanting to come off as pushy is a concern shared by nearly half of single men in the U.S. who grapple with “approach anxiety,” per a 2025 report.
Researchers determined that “perceptions of being labeled as ‘creepy’ significantly impacted American men’s willingness to interact with women, and 44% of 1,000 men reported that this fear reduces their likelihood of initiating contact.”
It’s an unfortunate trend that seems to clash with what the majority of single ladies actually want. Seventy-seven percent of women between 18 and 30 — and 68% of those between 30 to 40 — hope to “be approached more,” according to the insights.
If anything, Liv, a 20-something and part-time Long Islander, has the “utmost respect” for men her age who summon the spirit to appropriately and politely make a pitch for her heart, “because it’s so admirable, in this day and age, to actually have the nerve and the kahunas to go and do that,” she said in a social media clip.
However, men still need to tread lightly when doing so.
“…the problem is, a lot of men pursue women knowing that that woman is not interested in them,” said lifestyle content creator Viv in a trending vid.
“I cannot tell you how many times I had been diplomatic and respectful [while declining a man’s advances], and it has led to me being borderline harassed … I’ve had [men] follow me, I’ve had a man grab me,” she added.
Connell Barrett, a 14-year New York City dating coach, stands behind how Viv — and most women — feel.
“Respect does not mean retreat. The single, straight man should still lead the dating dance in the courtship phase to a certain extent,” Barrett told The Post. “Women aren’t saying, ‘Don’t come talk to us.’ They’re saying, ‘Don’t objectify, harass or disrespect us.’”
Since rejection is another fear that young single men face, Barrett, whose clientele largely consists of heterosexual men under 35, suggests they ditch the mental gymnastics of “what if” and instead approach women with grace rather than angst.
“Adopt a new mindset. You’re looking for love, which is very human,” he said. “It’s OK to say ‘Hello’ to women out in the world, as long as you do it with the right measure of empathy and charm.”
However, it seems the sweet, charming route might not always be the best option, at least according to Grant Greenly, a 24-year-old actor and model, who has taken this approach — both in-person and on dating apps like Hinge and Raya — to no avail.
Now, the Texas native is completely done with wooing would-be sweeties altogether.
“I’m never doing it again, and I mean that. I don’t care how it impacts my dating life,” Greenly told The Post. “Approaching women today isn’t worth the hassle.”
For Greenly, the final straw was a recent attempt to say, “Hi. How are you?” to a looker who immediately shut him down with a cold, disapproving look, followed by an “Eww. Who are you?” response from another single woman he attempted to chat up at a club.
“Dating is not like how it was back in the day. Our dads didn’t have to worry about phones and computers warping people’s minds,” he groaned. “Nowadays, guys, including the ones who aren’t creeps, get posted online as a joke when they ask a woman out on a date.
“There’s this deluded idea that all men are out to get women, no matter what.”
As a result, the Southwestern gent said if he’s ever going to meet the girl of his dreams, she’s going to have to make the first move.
“I don’t see anything wrong with the notion that women should approach men for dates,” he said, citing gender equality as the basis of his position. “I know there’s the argument that ‘Men used to go to war.’ But now, women go to war, so why can’t they do the approaching?”
Levi McCachen, 37, backs up this belief, thinking it’s time for women to step up to the romantic plate.
“I recently went out, and a woman who wasn’t the type of girl I typically go for opened up a conversation with me. It was great, and I got her number,” McCachen, a stand-up comedian and podcaster, told The Post. “I thought it was awesome that she did the approaching.”
“If you go up and say anything to a guy you think is cute, he’s going to be, like, ‘Holy s—t, this is the boldest woman I ever met in my life,’” added the Canadian.
The professional funny man and podcaster reiterated his call to action online, saying, “Men, we need to stop approaching women altogether. Women, it’s your turn.”
“I was taught that if I walk into a room of 100 women, 99 aren’t going to be into me,” he added. “But one of them will be, and she’ll let me know it.
“All I have to do is not f—k that up.”
