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........

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