Grandma's Boy (2006)

Plot: When his roommate spends the rent money on hookers, Alex, a 35 year old video game tester has to find a new place to live. After an "encounter" with his friend's mom, Alex is forced to move in with his grandmother. Trying to save face with his younger co-workers, Alex says that "a really cute chick said I could sleep with her and her two crazy girlfriends" (meaning his grandmother and her two roommates).

Alternative Plot: When he and his roommate can't pay their rent, video game creator Alex (Allen Covert) finds himself homeless and moves in with Lilly (Doris Roberts), his wacky grandmother. Lilly and her elderly pals like to hang out in front of the television all day, but their constant presence puts a damper on Alex's social life and pot smoking. Alex wants to court co-worker Samantha (Linda Cardellini), but he's preoccupied by a rivalry with another game designer, so the would-be relationship is in limbo.

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