Member-only story

I went in for the kiss on every first date.

The Kissing Dilemma — Should Men Wait or Take the Leap?

Trey Hamilton
8 min readJan 19, 2025

Yeah, I did.

Every first date, I went in for the first kiss.

But it wasn’t always like this.

I used to wait for the 3rd, 4th, and sometimes even 5th dates to kiss a girl. Why!? I was scared of being rejected.

Scared shitless, actually.

Until one day, I thought to myself, what if I just tried to do it on a first date?

So I did. The first time happened like this:

We were at a bookstore called Waterstones for all you Yanks; I believe you have Barnes and Noble.

We went there after a coffee. We were in a secluded part of the store on the 2nd floor and looked at her and said:

Me: Can I kiss you?

Her: Wow, I guess, why not!?

So we kissed. She laughed on the tube home about how bold it was, and no one had ever done that before. They usually went for it at the end of the date.

I can still see myself trembling to this day cause I was so nervous.

Going forward, that was my MO. If I liked her and always asked for a kiss. It did wonders for my confidence. Cause if…

--

--

Trey Hamilton
Trey Hamilton

Written by Trey Hamilton

Author - The First Date Fix - Dating Coach - Content Creator -Dog Dad | follow me for some ramblings of a millennial who has dated. A LOT! TheFirstDateFix.Com

Responses (1)