problems with socializing with the other sex

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So I have really hard time with asking girls I like out. I'm not exactly the worst of the bunch looks wise, probably at 6/10 and my body is nothing special. I have no really hard time with socializing, I have a tight group of friends and can navigate a social situation pretty easily. I'm pretty self-conscious when meeting new people and have a bad case of stage fright though.

The problem I'm looking advice for is that all that supposed semi-confidence goes out of the window when I think of asking a girl out. I ponder on it, spin it in my head sometimes for weeks, before either forgetting about it or in rare cases actually following through with it. Because of this I can't really just go in a bar and talk to a girl like most others seem to be able to.

I suspect this has something to do with my history. I was made a laughing stock for three years in my upper secondary, because I wrote a cringy admirer letter to one of the super popular girls. I was incessantly bullied for it until I got away from it in high school, but the baggage followed. I felt inadequate and that I don't deserve anyone. After all, who would want a naive, blue-eyed romantic who got raised up watching Disney movies?

I gathered up the courage once in high school to ask one girls out, but it ended in failure and rejection after a couple of dates, which subsequently made me quit trying altogether for some time. At this time my friends started getting girlfriends etc. which made me feel envious and angry at myself for being the way I was.

Only now in university have I forced myself to get used to the dating culture again, but because of my experiences I don't have any sexual experience, which makes me insecure too. I feel like I'd just fuck it up (no pun intended) if I ever get to play hide the sausage.

What do I do?

I don't have a good thread starting image so have a fluffy cat.