I think I saw him pull over and talk to a lady whering a little skirt and a pink top. They talked for a moment and then I heard her say "Are you f'n crazy!? I don't do BJs for ten bucks! Come back when you get money!

I saw him later talking to a man in a brown suit. The guy was old and there were dudes in black suits and sunglasses standing around them. I snuck closer and I heard the old dude say "knocker her off? No problem. My men are at the ready. The only thing we need to discuss is cash. How much you offer'n?"
"mumble mumble"
"Don't make me laugh! Come back when you get a job!"

At least I think it was him. Is this what Bob looks like?