I lost mine in high school, and kinda regret the way it went down? Basically I had a girl who wanted to be my GF and I wasn't into her nearly as much as she was into me, but I was too awkward to stop hanging out with her even after she started pushing me to become FWB (Part of it was that I didn't think she was that hot, part of it was that I wasn't emotionally mature/ready for a GF and I knew it). Basically she wore me down, and I gradually became okay with more shit, and so when she said we might as well just have sex at that point I said sure. I lasted like 1 minute, neither of us knew how to position ourselves right, and it fucked things up in the future. On the plus side, later when I met someone I really did want to be with, it worked out better since I had some idea of what the shit I was doing.