Wow I used to think MY most embarassing moment was bad... then I read some of yours!! Oh well here's mine anyway...
The summer after my senior year of high school my parents flew my best friend and I to Hawaii for a week. My friend and I ended up getting tanked (

) every night on our trip. After one night of partying particularly hard, we decided to go parasailing at about 11am. We get put in a boat with a family of 4, a young couple, an asian woman, and us 2. So my friend and I are the first up and its really fun and we're having a blast etc etc. we get pulled down and then have to wait the rest of the time while everyone else gets their chance at going up.
well we were on the boat for like 10 min when i start feeling REALLY sick. The water is really choppy and Im still pretty hungover and despite my best efforts to hold it in, I end up puking over the side of the boat. kind of embarassing, but not too bad.
so almost everyone else on the boat has had their chace at parasailing, execpt for the asian woman who was there alone. the captain of the boat asks if anyone will go up with her because she came alone. so im thinking: well the water is making the boat ride choppy and im getting sea sick, but when youre up with the parasail, its really smooth, so i wont be sick - ya know? i volunteer to go up with her, and they strap me in behind her.
so the asian woman (who speaks no english by the way) and i are up there for a few minutes and i start feeling woozy again.
"holy sh!t" im thinking to myself "do not puke. do NOT puke." and i try to distract myself from my nausea by thinking about any randomness that comes to mind.
finally, i cant hold it anymore. i try to cover my mouth, but that did NO good and I ended up vomiting ALL over myself AND the asian woman! i couldnt stop! it was all over the back of her neck! i was trying to apologize and say "sorry" between the hurls. and then she turns around and just says "sorry. sorry" and starts throwing up too!!!
so there we are. up in the air. both puking all ove. and the whole boats watching.
i cried for the rest of the day.