The Confidence Trap

More young men are struggling with anxiety and self-doubt, but in dating are too often told they need to be confident

None of us can resist a bad first-date story. They are ubiquitous in American culture. And like a train wreck, it’s difficult to turn away.

Recently, I came across a particularly memorable example on TikTok. The narrator was recounting a recent dinner out with his wife at a packed restaurant that put them inches away from a young man and woman who were out on a blind date. Things fell apart almost immediately. Within 30 seconds of sitting down, the young man announced that he just returned from a business trip to China where he learned that “business and sex are often one in the same.” Things only deteriorated from there. The date ended with the young woman fleeing the restaurant.

Bad dating stories abound on the Internet. And although admittedly anecdotal, men appear to be responsible for a disproportionate share of these dating disasters. Surveys provide some corroboration. A recent Pew survey found that among singles, women were far more likely than men to say it was difficult to find someone who meets their expectations. What’s more, men and women agree that it is men, more than women, who have unrealistic standards when it comes to dating.

The Self-confidence Problem

A wealth of scholarship has found that self-confidence, even the unearned variety, is an asset in nearly every facet of life. And men, at least in general, do not appear to be in short supply. But social conventions are changing. Today, men are instructed to avoid manspreading and mansplaining. In the dating context, however, many of the old rules still seem to apply. More often than not, men are still expected “to ask for, plan, and pay for dates; initiate sex; confirm the exclusivity of a relationship; and propose marriage.”

The confidence requirement in dating is tied up in traditional notions of masculinity. There is an expectation that men should know what to do in a given situation, even if they have never encountered it before. Taken to its extreme, the confidence imperative encourages men to refuse to ask for help, admit ignorance, or even acknowledge feelings of uncertainty. These public and performative displays of confidence can lead to unfortunate situations, ranging from missed-social cues to more egregious behavior.

In a recent Washington Post piece, author Christine Emba suggests that young men are struggling to navigate the dating landscape in the post-Me Too era. While some behavior is clearly problematic, other interactions fall into a murkier area: “You know enough not to be Harvey Weinstein, but what if you end up canceled like West Elm Caleb?” This heightened concern hasn’t gone unnoticed. One therapist told Emba, “Men in their twenties are terrified, and they talk about it a lot.”

Even as American culture holds up the importance of confidence in dating, for many men it’s not so straight forward. More than half (52 percent) of single men say one of the most important reasons they are single is that it is difficult for them to approach people.

A Deteriorating Social Life

When it comes to dating, one of the most significant assets we have is our social circle. Having a large and active social network provides abundant opportunities to meet lots of different types of people with whom you have some personal connection. Dating through your social circle may come with challenges, but it can also increase feelings of trust and safety. The problem for young men today is that their friendship networks are much smaller than they once were—a survey conducted in 2020 found that more than one in four (27 percent) young men reported having no close social connections at all.

The living situation of many young men may also serve as a social limiting factor. A recent Pew study finds that more than half of young men are now living at home, in large part due to the pandemic. The logistical challenges of dating while living with your parents are self-evident, but this trend might have other negative social consequences as well. Compared to previous generations, young men today are relying more on their parents for emotional support as opposed to their peers. Compared to their friends, parents might not be the best source of advice when it comes to navigating the current rules for dating, relationships, and sex.

It’s not only the shrinking size of young mens’ social circles that’s the problem. Compared to older men, young men are more likely to have gender-segregated friendship groups. More than half have few or no friends of the opposite sex. For heterosexual young men, the deficit of female friends is a major liability. First, it deprives them of an opportunity to hear the perspectives of women when it comes to dating, relationships, and sex. Previous research has also shown that “men who have female friends are significantly more likely to express their feelings and receive emotional support than are those without.” Finally, in a culture that regularly sexualizes and objectifies women, these types of friendships can serve as a potent corrective.

Online Dating and Social Trust

As their social support withers, it’s not surprising that so many young men are gravitating towards online dating. But online dating has its own problems.

The ubiquity of online dating belies how unpleasant most people find the experience. Nearly half of young adults report having used an online dating app or website at some point. But the ease with which dating apps connect strangers is part of the problem. As I wrote recently, the challenge of online dating is that it places “strangers with few if any shared social experiences, or contacts together, resulting in people having little trust in situations where trust matters the most.”

The problem with dating someone who has no connection to your life—who does not know any of the same people or run in the same circles — is that there are few if any repercussions for poor behavior. On the other hand, the consequences of ghosting your friend’s roommate are immediate. It can risk damaging a relationship that you care about. The strength of shared social bonds encourages people to be on their best behavior.

Communication is also far more difficult online than it is in person. It’s incredibly easy to miss social cues or misread intentions when you are communicating in characters. And because there are few rules or norms for dating online, it’s difficult to know when you are guilty of overstepping or where to draw the line.

And this is another reason online dating is so limiting. The lack of feedback. Dating online reduces opportunities for people to receive constructive criticism. Bad dates more frequently result in ghosting or blocking. But without regular feedback, it’s much more difficult to learn from our mistakes. If online dating encourages people to treat dating as a “trial-and-error process,” it rarely affords them opportunities to grow.

But where does this leave us? Too often, we focus on individual infractions without acknowledging structural problems that encourage or incentivize poor behavior. We focus on “locker-room talk,” but not the societal problems that allowed this environment to develop in the first place. A recent survey found that more than one-third of young men were criticized for not acting sufficiently masculine when they were growing up. A culture that shames a young man who enjoys cooking with his mother is part of the problem.

Social relationships are most successful when they are structured, the rules are well-established, and the road signs are clearly visible. Today, social rules and norms have become murkier, and there’s not enough guidance on how to proceed. We don’t have to excuse bad behavior to acknowledge the social and cultural forces behind it. If we want young men to abandon destructive social and dating behavior, we should stop telling them just to be confident and start offering better models for it.