Here is what I suggest.... go out and do it with a friend, and do the whole thing as a GAME, just the two of you fooling around having fun with each other and other people. This is how it should be done anyway... doing it with a wing can make it more fun and less serious (it SHOULD be fun and not serious!)
Now... I just wish I had a wing to apply my advice with
About a week ago I met a friend of a friend who doesn't know anything about PU, but I challenged him to it, we did just that on the streets of Bangkok for two nights. There was NO set that didn't blow-up to us, set down with us, spent with us at least 10 minutes if not 2-3 hours... We saw two girls sitting down in a restaurant and just came to them with "hey whats that soup you are eating" and were asked to sit down with them after about 1 minute. We could hang out together just two nights but the whole experience blew my mind.
My end goal is to be able to do it alone but... as with anything in PU- starting slow is key.... go out with a wing, have fun, fool around.. then take it from there. Why jumping to the deep end when you can make things easier?