I'm dipping my toe back into dating again, and of course I have absolutely no idea what I'm doing. This is a universal trait, of course. I do feel very comforable in the company of the opposite sex, but there are those inevitable moments when I feel like I'm assembling an IKEA set of drawers with one...


To answer your three questions, first remember this: EVERYONE in the dating pool our age has some baggage. They all are worried about making a good impression and dating has its risks for everyone involved. Don't anticipate that making bad decisions are inevitable or even a possibility when entering a dating relationship.
Instead... go into that pool, not with past dating/relationship failures hanging over your head, but with the confidence of knowing the good things about yourself.
If it is hard to identify those good qualities that would be attractive to a woman, ask a couple of female friends whom you trust. Going in with confidence in who you are will more likely help you to make better decisions about whom you want to date.