There is nothing in life more terrifying to me than talking to an attractive woman.

For years, I’ve told myself that I don’t know how to talk to women. It’s a convenient excuse. It implies that I need more knowledge, that if I just learned how, all my problems would go away. 

Except it’s a lie. 

Worse, I know it’s a lie and I keep telling it.

I’ve dated plenty of women. I’ve never sat down at a coffee shop or bar on a first date and froze up. They haven’t all gone well, but probably no more than my fair share.

So my problem isn’t that I don’t know how to talk to women.

A more honest statement would be that I don’t know how to meet women.

It’s the approach. The fear of rejection takes hold of me and I freeze up. Sentences that used to make sense seem quaint. Analysis paralysis tells me that I have to be incredibly charming. I try to figure out what to say to what she’s going to say to what I’m going to say to what she’s going to say to what I say.

No matter how many times she looks in my direction, I don’t have the courage to walk in hers.

And I’ve never really needed to get over this fear.

AOL Instant Messenger started to become popular around the same time I became interested in girls in middle school. Instead of flirting in person, I could just get a girl’s screen name, or better yet, have a friend give it to me. 

Like Brad Paisley, I was so much cooler online.

I asked my first girlfriend out on AIM in 10th grade. 

I Started flirting with my second via Myspace. By the time I got to college I had mostly transitioned to Facebook Messenger, but the pattern was the same. I could say things online I couldn’t say in person. 

I could be the person online I wanted to be in person.

I still remember where I was in 2013 when I first heard about Tinder, and who told me about it. I was already on dating sites then, but dating apps seemed like a whole different ball game. I could not wait until the Android app came out.

The medium has changed over the years, but I estimate that I’ve met at least 95% of the women I’ve dated via the internet.

The sad thing is that this is pretty common.

These days everyone is on dating apps. It’s gotten to the point that dating apps are ‘The Apps.’ And no one is having a good time.

I’ve been off The Apps since October of 2022, and as I approach dating again in 2024, I want to keep it that way. I hate how I feel on The Apps. It feels like such a meat market, like I have to constantly sell myself. I have to be the funniest, most charming, most extreme version of myself to wade through the sea of men. 

There has to be another way. 

I didn’t spend the past year not dating, fighting through my loneliness to go back to that. 

It’s only my fear that’s stopping me. Part of being a man is finding and facing the fears that keep us from being the men we know we can be. So I’m going to borrow an idea from the recovery community and commit to starting an in-person conversation with 90 women in 90 days beginning January 1st. 

One woman a day. 

Just one.

Attempting to talk to 90 women sounds terrifying. Talking to just one brings up a lot of fear, but seems doable. Just one brilliant moment of courage each day.

My hope is that I’ll encounter these women throughout the course of my daily life. But if this challenge means I need to make an extra trip to the grocery store, run an errand, or go drink a mocktail at a bar to find a woman to talk to, I’ll do it. 

Because I want to be a man of integrity. Especially with myself.

I doubt most of these conversations will lead to a date. Even less will lead a second. But even if none of these conversations turn into a date, I’ll still succeed. That’s the beauty of this challenge: I can let go of the outcome. 

And that’s really what’s driving that fear. An outcome I don’t want. A rejection that, when it comes down to it, probably says more about where she’s at than anything about me.

It’s just a loss of the illusion of control.

To keep me on track, I’ve asked men in my life to check in with me about it. And in doing, so I’ve been able to connect with other men around this fear. I’m also sharing about it here, and plan to post updates so I can keep myself on track and share what I’ve learned. 

If you want to hear about how it goes, please subscribe.

Throughout it all, I hope to keep the purpose of why I’m doing this front and center:

To improve my sense of agency in my dating life.

To improve my ability to connect with others.

To create a more satisfying love life.

And ultimately, to help me find a life partner. 

But all that happens one little step at a time.

So what are you doing in 2024 to become the best version of yourself?