I remember one night in Chicago, walking home after the gym.
Cold wind, hoodie up, headphones in.
I saw this girl at the crosswalk — exactly my type.
Soft eyes. Latina. Cute as hell.
She looked at me, then looked again.
And I did nothing.
I don’t know why that moment hit harder than others, but it did.
I kept walking, but my chest started tightening.
Not anxiety — shame.
It wasn’t about her.
It was about me.
By the time I got to my apartment, the silence in my room felt louder than the street.
I sat on my bed, shoes still on, and I remember thinking:
“Why the fuck didn’t I go talk to her? What am I scared of?”
And it was weird — because it wasn’t the fear of rejection.
I’ve been rejected a hundred times.
It didn’t kill me.
It was something nastier.
It was that I didn’t trust myself.
I didn’t trust that I could handle the moment.
Didn’t trust that I could say something real.
Didn’t trust that I was enough in that exact state I was in.
I kept playing out this fantasy in my head that I needed to be “on.”
More charismatic.
More confident.
More put together.
More something.
And every time I waited for that “better version” of myself to show up,
I abandoned the version that was actually here.
That’s what hurt.
It felt like leaving a younger version of me behind at the crosswalk
while I walked away pretending it didn’t matter.
But it did.
It always did.
The regret wasn’t from missing the girl.
It was from betraying myself — again.
And that night, I finally admitted it:
I wasn’t scared of her reaction.
I was scared of facing the part of me that didn’t feel worthy of being chosen.
That realization fucking stung.
But it also freed me.
Because the thing I was running from wasn’t women —
it was my own reflection in those moments.
And once I decided to stop running…
once I told myself,
“Even if I stutter… even if I tremble… even if it’s messy…
I’m still going,”
That decision didn’t make me fearless.
It made me honest.
I literally shook my body out in place, like I was resetting my nervous system.
And for the first time, approaching actually felt good —
not because I nailed it,
but because I showed up for myself.
And once I stopped abandoning myself,
something wild happened:
I started realizing how many women actually choose me.
Not a perfect version of me — me.
That’s when everything shifted.
Hope this helps out in your journey if you are going through something similar.
I hope this hits the way it needed to hit me.
However, what’s one moment in your dating life where you confronted something like this?
I’m genuinely curious.