Connell Barrett

We've got approaching, we've got online dating, we've got flirting, and how to handle yourself on a date.

Let me start with a story though.

I want to talk about the first make or break moment, which is the moment you decide you either will or won't approach that woman.

I remember

Many years ago, I'm in a Starbucks on Park Avenue, 29th Street, New York City, on a Sunday afternoon.

I had never approached a woman before, but that day I saw this really pretty brunette sitting by herself.

She's on her phone.

I remember she looked like Katie Holmes, who was my crush at the time.

She was my late 2000s crush.

And...

I walked over to her seat, her table, and I wanted to approach her, but I didn't.

I literally just walked around her table a couple times trying to think of the right thing to say, not coming up with anything good enough.

And I went and sat down.

thinking, okay, let me try again.

I was worried about other people seeing me and wondering how bad it might feel if I bothered her and creeped her out.

And I was also just worried that I would say the wrong thing and she wouldn't want to talk to me and that would make me feel shitty.

So I sit back down, I'm trying to think of something better to say.

And five or 10 minutes later, she walks up, leaves.

And I remember thinking, gosh, if I could have only gone and approached her, I might be on a date with her tomorrow.

I might have her in my life, but I don't now.