I love this thread! So many cringe-worthy stories.
In high school my two closest friends were prettiest/most sought-after girls in school and I always felt like their big lumbering friend. Both of them were about 5'2-5'3 and very slender/petite while I was 5'10 (which I'm happy with now but in high school I always felt like I was taller than 80% of the guys in school). I was pretty used to being ignored by guys in high school when my friends were around but a time or two it was particularly awkward and upsetting.
I transferred schools and I was asked out on a date by a guy from one of my classes. I really didn't know anyone and I think it was a bit of a relief to be asked out because I thought the guy was nice and it seemed like a good opportunity to meet people. I had a bit of a crush on him in class and I was flattered he asked me out. He suggested doing a double-date, which was fine so I invited my friend from my previous high school.
When the guys came to pick us up, my date took one look at my friend and for the rest of the "date" he and his friend (who was my friend's date) sort of competed for her attention, asking her questions, telling jokes and just sort of ignoring me. And then when we got to the place for our date... my date paid for her and not me. It was pretty humiliating. Then some other random guys came up and started talking to my friend and the two guys got mad. I felt like I was awkwardly trailing after some weird high school version of the bachelorette.
My dating life improved after high school.