Example: I was joking with a girl who travels to interesting places for work. I know she is interested. This is me making light conversation ,more or less for maintenance.

And I said " sign me up for bring a friend to work day"

She of course responded with "lol I'm pretty sure we don't do that.

I followed up with "have you told your boss bringing a handsome ...."friend" could boost work productivity?

It wasn't overly conceited, but I figured it might be enough for her to sense confidence.