If you had the ability to sleep with lots of women (or whatever gender does it for you) how can you be so confident that you wouldn't?

I dated a lot in college. Had subpar girlfriends in high school. I never had attention from women. When I was younger I had no friends and always dreamed of a perfect girl to save me from my miserable existence that I used to call a life. I thought I had so much to offer that someone would totally appreciate me and love me. How the fuck would I know otherwise?I didn't interact with people so there was no baseline of what a talented or caring person looked like. But I'm getting ahead of myself.

For every girl I dated, the bar was raised. For the last one I really experienced the darker side of relationships. The fights. The accusations. The indifference and the sheer pedestrian routine of it. I was bored. We grew to resent each other and it was worse than being alone.

That was many years ago. It took me about a year to get back on my feet. I thought I was hideous (I'm not good looking, maybe a 5 at best, but not the worst) had nothing to offer the opposite sex. But I was working in a job that forced me to be out going and warm up to people in a minimal amount of time. That job (as shitty as it was) made it at least possible to talk to women otherwise I'd be up shit's creek without a paddle. Slowly it started getting easier and easier. But I was still so terrified of ending up in a situation of pure boredom and resentment. So I started to casually date. Every time someone tries to make it official or I start getting comfortable with her I freak out and move to another girl.

I've been doing this for years now. Once the honeymoon phase is over, I'm out. Or I think I can do better. I still haven't done better than her. I dont think about her any more. But I don't think about her any less.

I have a lot of hobbies and I work my ass off. Because of that, to the untrained eye; I'm different, cultured, interesting. The truth of the matter is that I'm a giant fuck up and fail at everything so I try things until I barely grasp the basics then give up. That fools most people. I've been by myself for practically my whole life so I'm insanely independent and have myd shit in check: nice clean place, well-dressed, etc. But once again, I'm a fraud and it's all the input and collaboration of many women from my past.

Now I'm at an age in my life where most women in my age range are past their peak and age is rearing its ugly head (not that there's anything wrong with that, it's nature). They're getting divorced. Swearing off attractive men in exchange for balanced and reliable men. Or they're just damaged like you wouldn't even understand and I have terrible taste/ am scared of rejection.

Also because of all this dating, I've grown extremely indifferent. Everything is the same to me and it's rare that I'm ever surprised. People confuse my indifference for confidence. Apparently that goes a long way.

Now to finally get to the meat of your question: for the first time ever I have the ability to garner the attention of the opposite sex, my standards are way too high to settle, I'm too mentally banged up because no one hugged me as a kid, the only way I'll ever be happy is by being alone, and my 8 year old mentality only makes me feel appreciated/cared for when people want to sleep with me.

TL;DR I'm the male version of the overweight girl that lost weight or the girl with "daddy issues" archetypes.