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Picture this: A guy at a bar swirls his drink, eyeing a woman across the room. He thinks, Should I say hello? Then he remembers a conversation he overheard: Another man had exclaimed, “I’m not going to go up to a random woman in a bar. Who wants to be picked up?” And, in response, the woman said simply, “Me.”

It’s a funny moment, but it captures the challenge many young men face today. In a world that’s hyper-connected but also brimming with new rules, regulations, and unspoken codes of conduct, countless men end up in dating purgatory—unsure how to break the ice, how to keep the conversation flowing, and how not to come across as a total creep. Let’s dive into why guys are struggling to find the right approach, and how everyone can inject a bit of trust, good faith, and yes, maybe even romance back into the dating scene.

A Game of Numbers (That Doesn’t Look Good for Guys)

If dating is a numbers game, it seems the odds aren’t stacked in favor of men. According to a 2022 Pew Research Center survey, 63% of men under 30 identified as single—nearly double the 34% of single women in the same age group. Not only are there more single men, but they also tend to be more actively looking for dates or relationships: Half of single men said they wanted a committed relationship or casual dates, while only 35% of single women felt the same.

What’s behind the discrepancy? Richard Reeves, president of the American Institute for Boys and Men and author of Of Boys and Men, suggests several factors. Perhaps women aren’t defining relationships in the same way men are, or maybe they’re dating older guys. And yes, many young women are also dating other women. Beyond that, though, Reeves points to something else: the rules of romance have changed—and guys are missing the memo.

Fear Factor: The New Dating Mindset

Modern dating feels a bit like an extreme sport. One misstep and you’re out of the game—or worse, labeled with the dreaded “toxic” brand. Reeves has noted that young men are increasingly risk-averse. Why? Because they’re well aware of what not to do: don’t mansplain, don’t harass, don’t be that creep at the bar. But figuring out what to do—how to confidently approach someone without stepping on any lines—can feel like solving a riddle blindfolded.

Adding to the fear factor is the accessibility of pornography. With a few clicks, men can access sexual content without the risk of rejection or the awkwardness of a first date. A 2020 study found that 91% of men (ages 18 to 73) consumed porn in the past month, compared to 60% of women. When you can swipe to satisfy a basic desire, why put yourself through the emotional roller coaster of real-life dating?

Politics: The Third (Unwanted) Wheel

Politics has always influenced relationships to some extent, but it’s arguably more polarizing than ever. A recent American Perspectives Survey found that 52% of single women would be less likely to date a Trump supporter, compared to 36% of single men. Meanwhile, 60% of single women worry women would fare worse if Trump returned to office, versus 47% of men with the same concern. Young men as a group have shown more support for Trump in the 2024 election, which could very well limit their dating pool.

When politics looms large, every choice—including who to date—feels loaded with significance. If someone sees the other side of the political spectrum as an existential threat, they might not even consider a conversation—let alone a date. Cue more isolation, more frustration, and fewer second dates.

Building Trust in a Swipe-Right World

So how do we fix this? Even in the digital age, the basics still apply: trust, respect, and empathy. According to Reeves, both men and women need to give each other the benefit of the doubt.

Women can help by offering kind, constructive rejections—no one wants to be ghosted or ridiculed for just saying hello.

Men must learn to graciously accept “no” for an answer without doubling down or lashing out.

Once upon a time, people met at dances, at bookstores, or in line for coffee. They’d risk a hello, sometimes get shot down, but they’d move on. That inherent trust in each other’s basic decency is something modern dating apps, with their endless arrays of faces and instant matches, seem to have undermined. Suspicion has replaced serendipity.

In Reeves’s words, “This whole enterprise needs a lot of grace … and a lot of accepting people in good faith.” Yes, there will always be bad apples, but the bulk of humanity (men and women alike) aren’t scheming to destroy each other.

Dating, at its heart, is about taking a leap of faith—whether it’s in a bar, on a dating app, or even at a friend’s party. Men who want to succeed need to get comfortable with polite approaches and respectful risks. Women who want to meet someone new should stay open to conversation—after all, sometimes you do want to be “picked up,” if only for a friendly chat.

The good news is that, for all the cultural changes and political tensions, most people are just trying to find connection. If both sides can let go of their fears and assumptions, perhaps we’ll see a return to that old-fashioned spark—minus the cheesy pickup lines.

So, here’s to stepping outside our comfort zones, remembering our shared humanity, and maybe, just maybe, striking up that conversation at the bar—even if you think nobody wants to be “picked up.” You might just be pleasantly surprised.