Grandma's Boy (2006)

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).