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Season 3, episode 15: "The Bubble"

Liz's ridiculously good-looking boyfriend Drew lives in a beautiful-people bubble of what Jack describes includes "free drinks, kindness, and outdoor sex." His handsomeness is basically his only asset: he's a former college tennis player who can't hit a ball to save his life, a doctor who doesn't know the Heimlich maneuver, and an adult who thinks putting Gatorade on salmon counts as cooking. Liz breaks the truth to him and they both realise he's content living that bubble life. He ends up riding off on a new motorcycle that he most definitely does not know how to ride. It's worth watching this episode just to see Jon Hamm flex his comedic chops and smile like a doofy human Golden Retriever. And, of course, to look at his ridiculously good-looking face.