I too have yet to go on an actual date, but the closest I've come to one was about a year ago when I was home from college on a break, and a good friend of mine who happens to be a female, whom at the time I had not thought about dating because she's a vegetarian, was also home, and she suggested that we meet at Pizza Hut. Once we got there, everything went pretty much perfectly until her sister and friend come in and sit down with us. Since it wasn't really a date, it wouldn't be all that bad, except that the friend was the girl I'd had a crush on since at least 10th grade, and who goes to the same college as me, and whom I had been trying for years to work up enough courage to ask out. Awkward. (Incidentally, several months later when I did ask her out, her response was "Sorry, I'm going with my boyfriend." She said it more politely than that, but after four years of buildup, there's no way for that not to hurt.) Since I'm too introverted, that's as interesting as the story gets.