Just because she's being flirty doesn't mean she's into you
And it's not fun to turn down someone like that
If they're interested they're going to have to ask
in writing and notarized to make sure there' s no miscommunication

I still can't forgive myself for not having asked a chick for her number after I had a good dance with her at a party....25 years ago. She was very pretty, exactly my kind of woman, at least physically, which is presumably why I was afraid to ask. It made me realise that I absolutely prefer to deal with the pain of rejection than to deal with the resentment and self-loathing of not having asked a woman out, asked for her number or even just talked to her.

How my gun looks at me after 3 whiskeys on an empty stomach

This outcome is good either way tho.
If she was actually into you and didnt do anything about it at all for years, then she is an idiot and you dodged a bullet.
If she is lying then she just wants to make you sad and you dodged a bullet.

This is the sort of comment that no one believes but I'm OK with that.

The night before I left for boot camp, I had not one but two longtime female friends throw themselves at me, within less than an hour of each other. I slept with neither of them, didn't do more than kiss either of them, but we're talking sudden, "OK, what is she-oh wow ok-5 minutes go by" kind of kisses. I'd known one of them since the first grade.

Now, here's the part where you stop formulating your accusations of implausible humblebrag and it becomes relatable to OP. 😁

YEARS, and by years I mean DECADES of my life passed before I considered the possibility that it was anything other than "we're probably not going to see each other again after this, let me give him a treat to remember me by."

And let me tell you, when that sort of realization hits you decades later, it's on a whole 'nother level.

Not today, CIA.

I used to have a major crush on the brother of my best friend but never said anything. Mainly because i was a teenager and he was in his mid twenties and it would have made everything awkward between me and my best friend (it kind of feels forbidden where i come from). I think someone who seriously says something like this has nothing to lose or they know that nothing will ever happen anyway and they want to play mind games out of boredom or due to low self esteem.

I'm really glad I watched little miss sunshine while in highschool. I took this to heart and am so glad I did.

So I kinda had the reverse happen. I graduated high school and this girl I kinda liked told me on the last day of school that she had a crush on me. So we dated for a few months but it never went anywhere.

OP, I don't think you ever saw my sister's best friend in highschool.

Who is she?