#11: Ouch
This had got to hurt like a gut punch. Granted, to a woman in her early twenties, a guy in his mid-thirties might seem old. Still, it’s a bit much to go for the “date my mom” suggestion after a night of flirting. Maybe her mom had her young? Who knows, this could be the best thing that ever happened to him if he keeps an open mind.

I’m assuming he didn’t take her up on her offer, though. I mean, otherwise, there would be more to the story. Still, it would take me a few years to get over that oblivious dig. Hopefully, he took some time to get his head back on straight and went back into that brutal dating game… with women in their 30s.