Dear Reddit what was your most awkward experience asking someone out?

In HS i was always really awkward with girls, in one case i had band with a girl and we'd practice. She dealt with my weirdness and awkwardness. So one day i finally had the courage to ask her out. I was so blunt and weird about it and also not the best looking guy in the world. Needless to say it was a no and we never practiced again

Reddit what was your most awkward moment of asking someone out?