First of all, if you want to pick up a chick, you probably shouldn’t mention her father in your pick-up line. Particularly if her father was recently incarcerated.
Secondly, am I the only one who envisions this encounter as having been extremely awkward and uncomfortable for the woman he’s hitting on? Somehow, I don’t imagine he was Holmes-esque in noticing the lack of wedding ring. I picture him staring at her hands, and analyzing her face with an “I Farted” face as he tries to be sneaky in analyzing if he stands a chance.
My guess, however, is that he doesn’t.