Hmm. Second regret: playing a character that everyone assumed was a lesbian when, in fact, she was just interested in people (male or female) with specific outlooks on life. Strangely, the only ones that openly fit the particular criteria were female personas. There were a couple male characters she was attracted too for these reasons, but you know, they never once paid her any attention; or when they did, made it clear that other criteria that made them unsuitable for a relationship would crop up.
OOC, in regards to her sexuality I would just say, "Yeah, she's a lesbian, lol." Inside I kind of died a little each time, because I had created a pretty deep character that everyone just reduced to 'look, just another space lesbian'.
Other issues with that character aside, my favorite RP experience was my character "coming out" to a character she liked. I knew the response it would get. Obviously she was going to be shot down. I had done enough research to know that the other character was involved in another relationship, etc. It was just so awesome because it took years to get the character into a position to ask, and a few months to set up a situation where it would be appropriate to ask.
I've just always enjoyed a challenge, and playing something interesting and just enough out of the norm to make even social interaction a chore held a certain fascination for a time.