I think you're picking the wrong problem. This doesn't have to be dealt with on the object level. If you're not socially anxious you're social discovery autopilot works fine. One thing that helps me with social anxiety is to visualise myself in the 'close embrace' of Argentine Tango with other people.
I think at some level, social anxiety, particular when it manifests in relation to the opposite sex has to do with misunderstandings about what makes for positive sexual experiences. It's about instinctive interest, awareness and communications of authentic desire to fulfill our drive for autonomy, feelings of competence about what we're doing sexually, and feelings of intimacy, desiredness, loved and respected to fulfill our need to relate to others. When I keep that in mind in non-sexual social settings, I feel myself come in my zone!
As in, how do you find ways to meet the right people you talk to? Presumably, they would have personality fit with you, and be high on both intelligence and openness. Furthermore, they would be in the point of their life where they are willing to spend time with you (although sometimes you can learn a lot from people simply by friending them on Facebook and just observing their feeds from time to time).
Historically, I've made myself extremely stalkable on the Internet. In retrospect, I believe that this "decision" is on the order of one of the very best decisions I've ever made in my life, and has made me better at social discovery than most people I know, despite my dual social anxiety and Asperger's. In fact, if a more extroverted non-Aspie could do the same thing, I think they could do WONDERS with developing an online profile.
I've also realized more that social discovery is often more rewarding when done with teenagers. You can do so much to impact teenagers, and they often tend to be a lot more open to your ideas/musings (just as long as you're responsible).
But I've wondered - how else have you done it? Especially in real life? What are some other questions you ask with respect to social discovery? I tend to avoid real life for social discovery simply because it's extremely hit-and-miss, but I've discovered (from Richard Florida's books) that the Internet often strengthens real-life interaction because it makes it so much easier to discover other people in real life (and then it's in real life when you can really get to know people).