Season 1: Episode 9: Win, Lose or Draw
Ray gets tired of being treated like a kid at his father's poker game, so he ignores his father's advice. He ends up losing all his money to Frank! Debra wants Ray to act like a mature adult and ask Frank for his money back, but Ray is too stubborn. Meanwhile, it turns out that Frank was only trying to teach Ray a lesson--that you can always go to your father and he'll make everything okay.