While walking my puppy home from the dog park recently I passed two attractive women waiting outside an apartment building. They were looking good. Probably on their way out somewhere, waiting for their Uber. 

While walking up, I had the thought “I should say something.” 

Just go up and say hi. How’s it going? Something. Anything.

I almost never do. I walk by. I check them out. I think I should say something. But I don’t.

And that’s when the shame kicks in.

I’m not good enough. How are you ever going to meet women if you don’t talk to them?

What kind of man are you?

I don’t know why it comes back to a question of my masculinity. 

There’s some part of me that thinks “If I were a real man, I’d just know how to talk to women.” And must be less than a ‘real man’ since it’s something I struggle with. 

On some level I realize that it has nothing to do with women. There’s some part of me inside that feels incomplete. It doesn’t feel good enough as it is, and tells that if I were only able to go talk to pretty girls it would feel good enough, that I would be a ‘real man.’ But that sense of lack will be there regardless of my success (or not) approaching and meeting women.

That shame is why I stopped my “90 meetings in 90 days” challenge. 

Every time I walked by a pretty girl, my inner critic had one more thing to heap on me. Not only was I not a ‘real man’ because I couldn’t talk to them, now I had a goal that I wasn’t living up to. I was putting too much pressure on myself and living in my shame. 

I don’t have a good answer. I wish I did. I don’t know how to quiet that inner critic, and I don’t yet know how to open my mouth and speak to women. 

I do know that I’m not alone. 

Over the past several months I’ve talked to a lot of men about my attempts to date without dating apps. Without fail, every one of them says “good on you, man,” and “I don’t know if I could do that.” 

No one is having fun on dating apps, but the fear that comes with the alternative is even worse than the subpar results everyone seems to be getting. 

When I was younger I read books like The Game and dreamed of becoming a pick-up artist. Just being able to walk up to a woman and confidently hit on her, get her phone number sounded like magic. What a ‘real man’ I would be then. 

I never managed to become a pick-up artist, mostly because I would have a drink or two to get some liquid courage, and then end up having eight or ten more because I was still anxious (and I’m an alcoholic). 

But I’ve also talked to men who ran in those circles. Men who have approached thousands of women. And they’ve told me that fear in approaching never goes away. 

Maybe I just need to ignore the fear, make the approach and get more comfortable with being imperfect and afraid. Maybe I need to dive into the shame, figure out what’s driving that feeling of not good enough. Maybe I need to try out ways of meeting women that don’t involve walking up to them on the street or in a coffee shop. 

The right answer probably involves some combination of all 3. 

I won’t know for sure until I’m on the other side of it.

But I do know that I can’t solve a problem without acknowledging it. 

So here’s my acknowledgment: I’m a 33 year old man and I’m still terrified of approaching women, and that fills me with a lot of shame.