Well, I hope this is not cliche, but it sounds like you need some work on the old ego, or chatting up anyone is going to be tough!

Poor is relative...ugly is subjective...and quite a few folks like the bald thing...

And I'm antisocial, but I'm married and doing OK at the moment...

Depressed...well, there's books, there's therapy, there's meds...are you having any luck with treatments like those?

I have started relationships while in the throes of untreated bipolar II, and that is not fun...if you have a depression issue, it helps (though it is not essential) to have some treatment underway before embarking on a relationship. Makes the whole getting-to-know-you thing a lot more pleasant.