Hey, bro. Try this...
In your head, instead of having 'this can go extremely well' and 'this can go extremely wrong' labels... only have these two labels...
- This can go extremely well
- This can go extremely funny
that way, you don't have to worry about things going wrong, nothing can go wrong, because you HAVE to label it as either Extremely Well, or, Extremely Funny. Things that go 'funny' can always be used in stories in later interactions and be amusing to tell.
^That's how you can frame it all to yourself.
Now, in regards to actually approaching and talking to people, how are you doing it? In such situations you can aim to talk to people just socially. Check out this guy's videos, he's good at this sort of stuff...
http://www.yourcharismacoach.com/
Hope this helps, bro.
Love
~Finesse