Jack played by Jason Schwartzman is the youngest Whitman brother. He is the hopeless romantic of the bunch. He writes fiction based on his true-life experiences but denies it even though it is made clear as day. He truly plays up to being the emotional baby brother of Peter and Francis. He is so heartbroken over his ex he continues to wear the hotel robe from where he saw her last. Jack rarely even puts shoes on for most of the film but once or twice is caught in men's sandals. He finds a love interest wherever he goes and uses this as a distraction from his brothers on their trip.

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