A good ol' "fuck it" suites me. Then I lean into it full tilt, most times I am absolutely sure I am being ridiculous in the event that I put myself out there. I try to forget about it after doing it, stepping away and disconnecting. If I don't give myself that breather moment of, 'okay you did it, now relax', it will spiral into the sort of conversation you think about five years from now. Like that one time I pulled into the Starbucks drive-through and the conversation went something like this:
"Welcome to Starbucks! I am Becky, what's your name?"
"I'm good how are you?"
...
She had to ask for my name twice and we both pretended it didn't happen.
I've come to realize, acknowledging the awkwardness helps let a lot of things go.