I'm 28 and not had much sexual experience until getting into a relationship last year that I broke off after 6 months (she was 33).

After that I went on a string of dates with younger chicks. I managed to sleep with a 28 year old Latin girl on the first date who I was instantly attracted to. She wanted to see me multiple times a week from the start. That broke down a lot of self-limiting beliefs - never being able to sleep with attractive women or keep them interested, etc.

She's gone back to Latin Land and I managed to sleep with a 21 year old Chinese girl from NZ (2nd date).

All looks great so far. That second girl lost interest pretty quickly and my confidence took a hit. I've since (over the last couple of months) slept with a couple of women I wasn't that attracted to.

I've been on a good few dates since with women I wanted to sleep with (matched on Tinder) but wouldn't even kiss me on the first date for whatever reason (game).

I now have dates setup with a couple of attractive women and I'm already starting to sabotage myself. I keep thinking sure I can sleep with semi-attractive women or women who are desperate, but any attractive woman with self-esteem just doesn't seem to reciprocate. Now I'm already assuming these women I have setup dates with might like me over text but are not going to be into me in person.

I know it's a confidence issue, but it's a tricky chicken and egg situation. How do I convince myself I can attract and sleep with high self-esteem attractive women before attracting and sleeping with them?