The Modern Dating Dilemma: Fear, Respect, and the New Rules of Engagement

In today’s dating landscape, a curious phenomenon has emerged among young American men. Ryan Kessler, a 28-year-old cybersecurity analyst from Manhattan, exemplifies this new reality—he’s not lacking intelligence or charm, but rather is paralyzed by the fear of being perceived as a “toxically macho, bone-headed creep” when approaching women. “I never want to make the other person feel uncomfortable, and I want to be respectful,” Kessler explains, highlighting a sentiment shared by nearly half of single American men. According to a 2025 report, 44% of men surveyed admitted that fear of being labeled “creepy” significantly reduces their likelihood of initiating contact with women. This approach anxiety has created a paradoxical situation where men like Kessler, who genuinely wants to find “the one,” find their “interactions with women are very few and far between,” despite being actively looking for a meaningful relationship. He’s more comfortable making first moves on dating apps like Bumble or Hinge, where the context for approach is clear, but finds real-world interactions much more challenging because “a lot of the time, in person, women are not there to be approached.”

This reluctance among men appears to be at odds with what many women actually want. The same research indicates that 77% of women between 18 and 30—and 68% of those between 30 and 40—wish to “be approached more.” Liv, a twenty-something Long Islander, expressed having the “utmost respect” for men who appropriately and politely express interest, calling it “admirable, in this day and age, to actually have the nerve and the kahunas to go and do that.” However, women’s experiences with unwanted advances help explain men’s hesitation. As lifestyle content creator Viv points out in a viral video, “The problem is, a lot of men pursue women knowing that that woman is not interested in them.” She describes how politely declining men’s advances has sometimes led to harassment: “I’ve had [men] follow me, I’ve had a man grab me.” These concerning behaviors create a legitimate basis for women’s caution and men’s subsequent hesitation to approach, creating a complicated social dance where both sides are increasingly uncertain about the rules of engagement.

Dating coach Connell Barrett, who has worked in New York City for 14 years, offers a balanced perspective on this modern dilemma. “Respect does not mean retreat,” Barrett advises. “The single, straight man should still lead the dating dance in the courtship phase to a certain extent.” He clarifies that women aren’t saying “Don’t come talk to us” but rather “Don’t objectify, harass or disrespect us.” Barrett, whose clientele primarily consists of heterosexual men under 35, suggests that men should abandon the mental gymnastics of “what if” scenarios and instead approach women with genuine grace rather than anxiety. “Adopt a new mindset. You’re looking for love, which is very human,” he advises. “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.” His approach seeks to balance respectful behavior with the traditional expectation that men initiate romantic interactions, acknowledging that complete avoidance of approach isn’t the solution to the problem of harassment.

Yet for some men, even well-intentioned approaches have led to such negative experiences that they’ve sworn off initiating romantic interactions entirely. Grant Greenly, a 24-year-old actor and model from Texas, has reached this breaking point. “I’m never doing it again, and I mean that. I don’t care how it impacts my dating life,” Greenly declares. “Approaching women today isn’t worth the hassle.” He describes receiving cold, dismissive responses like “Eww. Who are you?” when attempting simple, polite greetings. What particularly frustrates Greenly is the public shaming that can follow a respectful approach: “Nowadays, guys, including the ones who aren’t creeps, get posted online as a joke when they ask a woman out on a date.” He perceives a societal assumption that “all men are out to get women, no matter what,” which has fundamentally altered how he views dating. As a result, Greenly has decided that if he’s ever going to meet someone special, she will have to initiate contact, citing gender equality as justification: “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?”

Greenly’s perspective is echoed by Levi McCachen, a 37-year-old stand-up comedian and podcaster, who believes it’s time for women to take more initiative in dating. McCachen shares a positive experience: “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.” He suggests that men might be pleasantly surprised by women who approach them: “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.'” McCachen has even made a public call to action, saying, “Men, we need to stop approaching women altogether. Women, it’s your turn.” His philosophy simplifies the complex dating landscape: “I was taught that if I walk into a room of 100 women, 99 aren’t going to be into me. But one of them will be, and she’ll let me know it. All I have to do is not f—k that up.” This stance represents a growing sentiment among some men that the traditional expectations around initiating romantic interest may need reconsideration in light of changing social dynamics.

The current state of dating reflects broader societal shifts in gender roles and expectations. On one hand, there’s a growing awareness of the harassment women have historically faced, leading to legitimate concerns about unwanted approaches. On the other hand, there’s confusion among well-intentioned men about how to express romantic interest respectfully without being perceived as threatening or inappropriate. The result is a communication gap where many women wish to be approached more, while many men are increasingly hesitant to do so. Some, like Kessler, continue to navigate this uncertain terrain cautiously, while others, like Greenly, have opted out entirely, expecting women to take on the traditionally male role of initiator. Dating experts like Barrett suggest a middle path—approaching with respect, empathy, and charm—but the ongoing dialogue about appropriate behavior in dating continues to evolve. Perhaps what’s needed is greater communication between genders about expectations and boundaries, allowing for genuine connections to form without the anxiety and miscommunication that characterize much of modern dating.