So I do a lot better with quantified goals than vague goals sometimes, and especially goals I can break down into little pieces.
I've not been going out and getting socially acclimated a lot, so I set a goal to go out and do some social activity involving strangers at least once every 10 days (I can change this over time naturally). I use an online tracker that ensures I meet an average over time, which I've been using all year for some other goals with a lot of success.
I started with something really easy, a movie meetup. It went pretty well. I had a conversation with a couple interesting guys before the movie. I'll go to the one next week if my schedule allows.
The anticipation for these new things is often a little scary, but the event itself is pretty calm. Seems like there's always other new people anyway.