Before I found StreetJelly, I played a few shows on Chatroulette, which is a website no one should ever go to. Ever.
My most embarrassing moment was a full band performance at a large music conference. Biggest audience I've ever played for, but the power to the PA and our instruments kept shorting out in the middle of songs.
My favorite guitar to play is a butterscotch blonde Telecaster, named after my daughter.