My most interesting Valentine's Day occurred when I was single. I had a roommate, she was cute but dated women. (When she was sick once, I went out for cough meds and brought home a girlie mag - it was a weird but fun experience looking over naked women with another woman!) Anyway, we decided weld get together and have a date, just for the hell of it. I remember getting dinner somewhere cheap and going to a movie.
The most interesting part was when she had me pick her up at work. She was at a strip club as part of the entertainment, and she had me show up when she went on stage! I had a big goofy grin on my face, I'm sure.