In July of 2025, I was at a country bar in Arlington, and a girl in a cowboy(cowgirl?) hat caught my eye. She was with three friends — not ideal, but oh well. I told my friend I was going to approach her and beckoned him to follow me. As the two of us walked across the room, I awkwardly stumbled as I passed another person. Shit. I took a left turn to a table and said that I had lost my nerve. “If you don’t,” he told me, “I’ll tell her what a pussy you are.” Well, guess I don’t have a choice now. I walked over and offered her a dance to the just-beginning song. I am not a great dancer, but I knew enough to adequately fill three minutes (three minutes is a lot, actually — the longer tracks scare me).
After the song, I tried to talk to her over the reverberations of the music for a few minutes. She was a recent graduate from a local university, she said, was currently working part-time but looking for more, and lived not too far from me. I proposed we continue the conversation over coffee later. She agreed, added my number, and promptly shot me a text. “I can’t believe that worked!” I told my friends. But it was not to be. She never did respond to my coffee proposal that was sent the next day — nor to my subsequent ice cream proposal.
I cite this incident not to mourn the conversation we never had and coffee I never drank, nor even to ponder the what-if of the stranger I so briefly met. In fact this counted as a win: at 26 years old, that was the first number I had ever gotten. When I reported back to my coach, Kahlah, she told me not to sweat it and that she was proud of me for making so much progress.
Hiring a dating coach is unusual. Struggling with dating, however, is not. For a lot of young people — certainly young men — dating feels like an elaborate humiliation ritual, where you try to get girls with seemingly (and on dating apps, literally) thousands of options to give you a chance. Many a sensitive young man might ask himself: why bother?
A shockingly high percentage are not, in fact, bothering: a full 45 percent of men aged 18 to 25 in a recent survey reported having never asked out a woman in person. In all likelihood, the fact that I’ve asked multiple women out in real life and gotten “yes” more than once puts me as above average in my age cohort… which is not a fact that inspires confidence in the future of American gender relations.
To understand why I chose to hire a dating coach, you need to know a little about me. Growing up and even in college I had effectively zero dating experience. I was anti-social and struggled with maintaining friendships, so I didn’t know how I would even begin to try dating. So, I didn’t. Like a lot of men, I used video games to dull the feeling that I was missing something. As I got older, I figured that I had nothing to offer until I had a good job, so I should wait until then. I graduated college in the COVID years, so that took time. It wasn’t until after I had finally got my career on track that I had some time to reflect on what I really wanted out of life and how I was going to get it. So, I started trying to date at age 25, totally barebones.
To say it went poorly is an understatement. I tried taking the same approach I took in my career: I would be kind and obsequious, while also being cautious and careful to avoid offense. That way, I would always put my best foot forward — or so I thought. After a couple of failed in-person approaches and a long distance situationship that appeared promising but petered out into nothing after a few months, I was distraught. Clearly I was doing things wrong. I decided that this was so painful that I never wanted to “fumble,” as the kids say, again. But how?
I decided that Blaine Anderson’s team might have the answer. She had a big footprint in the podcasting and social media sphere, and as a creature of such things myself, I found that appealing. Without getting into too much detail, there are a few different aspects of coaching. There’s an online curriculum to watch at your leisure — you could watch it all in one day, though I suspect it’d be difficult to properly absorb. To make everything stick, it’s recommended that you watch a little bit and then integrate what you learned into your life over a few weeks before you move on. There’s also a direct, one-on-one portion with a coach that features regular ~hour long video calls and 24/7 email communication that lasts around 6 months.
One of the first lessons I learned is that dating is a bit like marketing. There are concrete things that you can do to increase your overall “value,” but human beings are too complex to be plugged into some input-output equation. Sad to say, if you’re looking for a magic thing to make that one person buy your product, such as it is, what you’re actually looking for is a miracle worker.
Another important takeaway is that in order to have dates, you need to be willing to have bad dates. You need to be willing to be awkward and faceplant in humiliating ways that make you want to curl up into a fetal position and consider that, you know what, that .357 Magnum barrel sure seems tasty (this is a joke — I don’t own anything in .357).
The kicker for me was confidence. Real confidence, I’ve learned over the past few months, isn’t knowing that you’re never going to be awkward or that you’ll never get rejected. It’s knowing that those things are just part of life — table stakes — and that you’re going to be alright even when they happen.
“I’m going to give you the recipe,” a common refrain from the course goes, “but you have to bake the cookies.” All the advice in the world isn’t a replacement for getting out there. Hell, if you’re a young guy, just by doing that you’re setting yourself apart.
What’s the value of a dating coach then? For me, beyond knowing the “hows” better and having an expert to consult with, I knew I needed some structure to hold myself accountable. Now more than ever, it’s easy to stay inside by yourself, avoid the hard things, and shut out the world. Put simply, I wanted better for myself. As the Male Loneliness Epidemic™ drags on, I suspect more men will too.