The Headmaster

Gavin and his ex-wife bring their son to the school for his interview and they're worried that the haircut he got might not make a good impression on the head master. So they bring Skylar along who was the one who brought their son for his haircut to explain. But when the man meets her he can only think about hooking up with her. Later when they go to his place, he makes a move which she rebuffs. And when Gavin and his ex hear about it, they're worried this ruins their son's chances.

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S02E15 - Nipplegate - Getting Dressed With Pamela