He said, "You know. Help me out?"
"You mean pay your bill?" I replied.
He said, "Yeah. I mean, yeah, I guess. Or... like... maybe like take some stuff off or something...?"
After I assured him there was absolutely no way I was paying his tab for him, he went back to the table and I awaited the inevitable dine and dash. To his credit, he walked back up a few minutes later with his date's card and was very apologetic.
It's probably the only time a stranger has asked me to give them $100, and definitely the only time someone has asked me to straight-up pay their tab.
I don't think the woman left happy.