75% chance it's the guy

Or a “can do” attitude.

The way I understood it, they're all friends and some people I know are like that with their close friend. Weird to me but whatever floats their boat.

Nothing wrong with being confident. There are girls I would drink with and say I have a 0% chance of getting laid, because I know that’s the truth.
There are other girls where if I drink with them, I would say it would be unusual if I didn’t score. You may not have confidence to pull this off, but let OP live his best life.