Best Five-Dollar-Per-Person Date (2008)

Harold nights at the Upright Citizens Brigade Theater

Thursday nights are Harold nights at the Upright Citizens Brigade Theater—two teams of the comedy troupe's apprentices doing half-hour group improvisations on random topics, based on a set of rules invented by Second City's Del Close. The Harold is usually hilarious; it's cheap, it's intimate, and by its nature it'll give you some shared in-jokes for later. And the first set ends conveniently early, so you can grab a bite to eat or stop by an apartment afterwards.

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