Ok, so I have a pretty low self esteem. Came to an epiphany a couple of days ago, and have been really down in the dumps as this realisation has come to me. I feel as if I have opportunities that I don't act on. For example, I asked a girl what she was up to for next week (and then invite her on a date for the days she suggested free. It was late in the week so I was also scoping if she was going out on the weekend) but she said she was really busy during the week. Her messages were then the following:

HER: What are you up to this weekend?

ME: Literally nothing, have like twenty dollars left so I'm pretty broke right now haha

HER: Surely use that leftover money to come out again!

ME: Maybe.... are you going to __

HER: Yeah, I've got an event there

So I go there with some friends. She's just at the entrance so I see her, give her a hug, and then head to the bar with my friends to get some drinks (because we were there to celebrate one of my friends' birthday). My friends and myself sat down at a table and were chatting, and she happened to be in proximity lots of the time. Could tell she wasn't looking directly at me, but a couple of glances and peripheral. Anyways, I just can't get myself to go over and chat when she's talking with her friends. I guess just everything in my life has never turned out well and I have always failed (school, sports, women etc.). I feel like I've blown this opportunity. Not much I can do about it unless I see her around, but I'm just too embarrassed to do anything about it now. Didn't even speak to her... So disappointed in myself, this self-esteem issue is really eating at me.