Jayson, you sound a lot like a young man who worked for me a few years back. He was smart, shy, liked gambling at the local card clubs, and lived with his parents. And, oh yeah, on one of his earlier jobs doing demographic sampling if his crew finished early the supervisor would take them to a strip club.
He would ask me for tips on how to ask a woman for a date; he'd never been on one at age 26. I suppose he trusted me, a mid forties Hispanic lesbian more than anyone else for this sort of advice. ( Miss Anna, there was a Nordic blonde woman at the market, she adjusted her hair while looking at me, do you think she was trying to get my attention? That sort of thing. )
His favorite radio station was KPFK, a strongly left wing oriented broadcaster. They had a Friday morning show with a community involvement opportunities segment; I suggested he go to some of these and just make friends. He did and became less shy.
Ultimately it turned out he just didn't quite have what it takes to work with us, a shame as I really liked him. I used my Power Dyke Super Rolodex to help find a job for him that was a better fit for his skills. I check every once in a while and he's still there, he's dating now and enjoys life more.
Jayson, perhaps you could check to see if there are any shyness support groups in your area, or maybe community groups that would fit your interest.