In grade 8, I was hanging out with my "friends" in a forest on our school's property. At the time, I had a crush on this one girl who lived very close to the school. One of the guys who I was hanging out with, who shall remain nameless, stalked this girl while she was walking home and found out her exact address. Nameless then told me that he discovered her house and told me to ask her out right then (about 6 pm). So I walked up to her door knowing that I could not go back. I rang her doorbell and experienced the most autistic thing I have ever done. Her sister opened the door, and while she held it open, I saw her whole family of five eating dinner and staring at me. I asked to talk to my crush and was greeted by her brother and then finally her. I proceeded to ask her out right then and there. I got rejected and walked away, literally shook. What terrified me even more was the fact that her mom worked, and continues to work with my mom. The next day I proceeded to yell at Nameless and got in trouble. I don't know if my parents found out about this but I'm sure as hell not gonna ask.

TL;DR : Asked out a girl I liked in front of her family.