Not too long ago, I psyched myself up to do it, it was my way out of my rut. All I needed to do was seal the deal and I could have a casual relationship, fix my confidence and be happy.
I went to a reunion we were having, and the wait for her arrival was grating. Nobody was around, and it seemed incredibly easy to get it over with if she turned up. It felt like purgatory. Then people turned up all at once, including her and her ex, who proceeded to flirt with her, destroying any opportunity I could have possibly had to fix my problem. Everyone offered me to join them hanging out at the park, but I didn't want to torture myself any longer, I just went home. When I got in, I cried silently.
That's basically the story for every single time I've tried.