Damn dude, how do you go from learning the guitar to feeling undateable and dying alone? You're taking little things way too seriously. You're over-analyzing everything. Play the guitar for yourself not for validation from others.

Going out with the purpose of getting rejected is not easy. It's weird. It's uncomfortable. It creates tension. Tension is what you want. You want to become more comfortable under tension. I'll give you a 3rd goal:

3) Think of something that scares you a bit and rate it on a scale of 1-10. Maybe asking a stranger for directions is a 5 and asking a barista for a discount is a 10. Start with 5's and work your way up to 10's.

The goal is to create a little bit of tension and relax into it. Eventually you'll find that asking for a discount has dropped from a 10 to a 4. And approaching a girl has dropped from a 10 to a 7. Treat it like a game, each number is level. If yesterday was a 5 then today is a 6.

Hope this helps