Seriously man, that would suck after a while..or just be plain old weird. But for this dude, he chose to capitalize, prey on the situation. Kind of wonder if him and the chick have met at this point, or established a system.

As far as the worst possible scenario to unfold for a dude who has a strange, pressing desire to get into a conversation about his dick; this is pretty damn brutal, man. A solid, proper trolling that he invited upon himself.