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The gang recounts their worst Valentine's Day experiences in order to cheer up Ellen.
Sophie encounters an obstacle with a new beau. Ellen uses her new job insurance to see a therapist. Jesse gives Valentina a hand at work while Sid and Charlie try to sell terrible wine.
Jesse and Sid introduce the gang to an old college ritual. They all spend the next 48 hours attempting to complete various tasks in order to achieve a group "rewardishment."