Yeah, I've asked out a handful of girls.
First one was in kindergarten, she was my girlfriend for a couple days or something. It felt more like a friendship, though. She broke up with me on the bus and I cried. I was 5, eat me.
In first grade, left a love letter on a girl's desk, got ripped on hard for that. I don't even remember why I did it, or what her name was.
Next time was freshman year of high school. I was the token weird guy, she was the token weird girl, our friends really had to encourage us because we were both so stuck in our own heads all of the time, even though we liked each other. She was my girlfriend for about 3 weeks, got two dates outta that and kissed her on the cheek. I shook her dad's hand, too, which really stuck with me for some reason. That was around the time I started getting into ne'er do well shit such as prostitutes, but she was a good girl. She couldn't handle how edgy I was being, and I was rather lukewarm to her despite how much I enjoyed hanging out with her. I shoulda known that something was wrong with me right then and there.
Last time was last year, met a interesting woman at a company training thing, asked her out to dinner while we were on our lunch break. She ended up cancelling on me, I actually felt relieved.
That's gonna be the last one, though. Turns out I'm gay. Thanks for reading.