Sometimes I forget this happened, but it was so long ago, I copied this from a comment I made, but edited it a bit more here...
2003 - 2004?
Middle school or early high school (I don't understand well your USA system), one girl asked me to be her bf (maybe as a joke idk, her 2 friends were with her and basically told her to speak to me), i literally did a 180 and said bye, just wasn't into those things yet, only cared about watching Digimon and stuff. Typical nerd with thick glasses.
I always considered her physically unattractive but she was mostly a sweet heart with everyone, soft spoken, her mom was a religion teacher at our school.
Anyways, next year, hormones were doing its job I guess, she looked the same ugly duckling to me, but she also... I dunno, like something was calling me towards her. Funnily enough we got closer and for a short while became friends (since we got paired to do homework and stuff together a couple of times at school) and I though many years later, even to this day "man, I should've said yes, even if it was a prank or a short thing".
She became the girlfriend of the only "jock" (for you Americans) of the class about 3 months after my "rejection".
And that pretty much is my only type of relationship with the other sex. Never felt in love or got into a relationship. Even if the whole thing was a cruel prank to make fun of me, that would've been better than not experiencing anything and still dateless to this day. Especially since as a kid you don't need money, dress well, speak well or a car to really start dating (especially in a poor country like mine), meanwhile as an adult in mid 30s, in Europe is basically mandatory plus having great social skills.
I feel like this works both ways. See Bowling Alone. Loneliness is a rising statistic, though unlike others I see isolation/escapism(/internet usage) as a symptom not a cause. I think money is a big reason.
Not sure about OP, but some of my perspective is from living in a tiny village in car-centric USA so there is not much social here for me, if anything at all. The "my people" are probably out there, perhaps even nearer than I think but that doesn't mean we'll ever have reason to know each other.