Dating is tough. And for many single straight young men, it can feel downright hopeless. 

As a man in his mid-30s, I can attest to this. When I was younger, meeting a potential partner felt so accessible. In school, it’s easy to meet women your age who have similar interests and hobbies because you’re in the same classes and extracurriculars.

Then, in my mid-20s, right around the time I was embarking on my new career away from home, dating apps hit the scene, making it easier than ever to swipe, meet people, and go on dates.

But in the years since, dating apps have become “enshittified”. You’ve got to pay Tinder, Bumble, and Hinge for higher profile visibility, and to see your potential matches. On top of that, we had a global pandemic that allowed folks like me to work remotely but also removed a lot of the daily social interactions that could eventually lead to a relationship.

So when a 20-something Vox reader and podcast listener told me over the phone that he too was struggling to date, I got to digging to find out why — and what could be done about it. 

It eventually led me to Charlie McKeever, who calls himself the “Happy Man Coach.”

McKeever works with men one-on-one in Austin, Texas, in addition to organizing retreats and weekly meet-ups, to troubleshoot men’s dating and relationship troubles and their broader vulnerability issues. He invited me to one such gathering at a bar called The Water Tank, where I met some of McKeever’s clients. I was blown away by how self-aware and enlightened they were. 

“You can call me a dating coach, but I would call myself a confidence coach,” McKeever explained. “That’s important for dating, it’s important for relationships, and it’s important for life. So I help men own themselves, to get to know who they are to reclaim themselves in their life.” 

The guys in McKeever’s group were realistic about how men like themselves can struggle to pursue relationships. Steve, a man who dated aimlessly for years, but recently found a partner, told me about a recent conversation with his friend. “My friend was talking about, ‘I wanna manifest a relationship.’ And that basically meant to them, ‘I wanna wish for this to happen.’ And they thought that that was going to actually work,” said Steve, whose last name is being withheld so he can speak freely about his relationships. “And I was like, well, that’s not gonna work … You have to be like, ‘I want this and I am going to take action by doing that.’ And go do it. It’s like an action-oriented thing.”

McKeever shared some of his insights with the host of Vox’s Explain It to Me podcast, Jonquilyn Hill. Read an excerpt of their conversation, edited for length and clarity, below. And listen to Explain It to Me on Apple Podcasts, Spotify, or wherever you get podcasts. If you’d like to submit a question, send an email to askvox@vox.com or call 1-800-618-8545.

What kinds of men do you coach? And what are some of the general issues they’re having with dating and romantic relationships?

In general, men are very feeling. We’re also very mission oriented; very singularly focused; and we like to succeed. We don’t want to fail. I’m a big fan of Alison Armstrong‘s research, and in it, she says that a man doesn’t want to do something that he doesn’t think has a high probability of success. So he’s going to only do the things that he thinks are worth it, right?  

At some point he has to learn that he needs to be himself and be who he enjoys being in his life and then do things from that place, right? Doing it as a happy, whole, contented person. And then he’ll see things from a perspective of abundance and not from a place of scarcity and lack, which is where we come from when we think that we need somebody. We need a person’s approval. We need their acceptance in order to be okay. And if we can only be okay if [we have it] then we’re really in a very precarious place.  

Loving yourself is all well and good. But what do you say to a man who’s doing the work? They love themselves. But they’re still looking for “their person.”

That’s totally legit. And there would have been a time that I would have eye-rolled at all of this, too. But this work doesn’t come down to magic. There’s no secret. It’s really very logical that when I’m dependent on something outside of me, then I’m going to feel very powerless. I’m going to feel very choiceless. I’m going to feel very victimized by the other person. And that’s just not a great place to be. It’s not a great place to live.

One thing I hear from men quite frequently is the word intimacy. They talk about intimacy. They talk about connection. The thing that we don’t know, that we don’t realize, is that intimacy is not just sex. At the end of the day, what we really want — and this is the part that [men] are kind of confused about — is that we really want to be seen. We really want to be heard. We really want to be understood.

And the interesting thing about intimacy and being seen and being heard, being understood, is that if we’re in this place where we’re protecting ourselves, where we’re trying to get something from somebody, the thing that we think that we don’t have, then we actually subvert that connection. If we just blame the external, then what happens is we feel powerless. We feel dependent, we feel choiceless, and we don’t recognize how much we’re influencing our own situation.  

How would you advise a young man who is not comfortable with approaching a woman in real life? Maybe because they worry they will come off as creepy or cringe? 

If we believe that it’s not okay to be ourselves, that it’s not okay to bother somebody, not okay to approach somebody — that it’s cringe, that it’s weird, that it’s whatever — then we’re going to disengage. We’re going to disconnect. We’re going to avoid. Because if the idea of walking up to somebody and talking to them is painful, then we’re going to avoid it. We’re not going to want to engage in that.

This is where men’s work comes in. If I’m living my life from the outside in, not the inside out, then I’m going to say to myself, “It’s not okay for me to go up and talk to that person, because I can only be this and I can’t be that.” But what we’re really wanting — what we’re walking around hungry for, desperate for — is acceptance. But if we don’t accept ourselves first, if we don’t say it’s okay to be me, then we’re never going to believe that it’s going to be okay to go up and talk to somebody and share ourself with somebody.

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