I finally did it. I was at a bar went up to a random cute girl that was standing alone and asked how her night was going we talked for a bit then her friend (girl) came and it got kind of awkward so I said nice to meet you to both and shook there hands haha I left and then came back 5 minutes later saying I don't do this very often but I said she was really pretty and if I could get her number she then seemed a little disappointed and said she had a bf but I was the sweetest guy ever. I said he was a lucky guy and left.

I didn't get a number, kiss, or anything but God damn it I finally approached. Felt good. Nothing bad happened and none the "bad" scenarios that I made in my head happened.