My cutest experience with being asked out happened with seeker5, on this forum!
Seeker and I met on this forum. We were heavily flirting with each other in one thread here and at some point I said "Hey, how about a blindfolded date?". So technically, I did ask him out, although I was kidding. We joked via PMs about this date and about how we'd wear wigs on the date. But then, he asked me out seriously, and even crossed the ocean to date me! We spent the evening walking around in the city, both wearing a green wig.
I was very impressed by his resolve and found all this very cute.
