How to date without murdering your self-esteem?

I'm pretty insecure about being a virgin so late in my life and it's kind of a snake biting its tail situation. Obviously being insecure is very unattractive, but what would help me with this insecurity is exactly what the insecurity is preventing.

I've tried Tinder but honestly I'm just not someone who can just take rejection after rejection on the chin and keep trucking, or see my profile barely getting one like per day without getting depressed and feeling like shit about myself.

But on the IRL front I haven't been very succesful either. I have a few female friends which I enjoy spending time with, but not many women seem to see me as a dating prospect, and I rarely see any girls being interested in me (I have a hard time warming up to people too).

I just feel like I'm in a knot that I know how to break out from. I don't think I need therapy since I'm OK in every other regard, I have a job, a degree, a social life. etc. I think it just boils down to being…scared? of women I'm attracted to.

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