Grandma's Boy follows a 35-year-old video game tester, Alex (Covert). The movie starts with Alex and his roommate playing video games together, when their landlord (Schneider) informs them that they are being thrown out for rent delinquency, which turns out to be because of the roommates penchant for Filipino hookers.
After trying to crash with his friend/weed-dealer Dante (Dante), Alex is offered a place to stay by his Grandmother Lilly (Roberts). He politely turns it down, and goes to stay with his friend/co-worker Jeff (Swardson). But after being caught masturbating by (and ejaculating on) Jeff's mother, Alex winds up spending the night at the office.
Alex is woken up by Samantha (Cardellini), a consultant hired to help with game development. While Alex demonstrates his gaming prowess with some of the younger employees, Samantha has a meeting with the company owner, new-age nut Mr. Cheezle (Nealon), and meets the story's antagonist, game design prodigy JP (Moore).
Alex is soon humbled into accepting his Grandma's offer of a room, and meets her roommates, over-sexed Grace (Jones) and over-medicated Bea (Knight). The ladies soon have Alex doing odd-jobs and chores around the house which leaves him exhausted, and subsequently begins to affect his job performance. Alex's co-workers Jeff, Barry (Hill), and Kane (Yu) prove to be no help, and Alex is forced to think of a plan. An acquisition of a black-box backfires on him, as the ladies become infatuated with Antiques Roadshow, and don't allow Alex access to the TV, which he needs to finish his work.
Alex figures out a way around this. He offers the ladies tickets to the show, and gets them to go to bed early. After a motivational joint, Alex manages to finish his job. The next day, after a meeting, Alex, Samantha, Jeff, Barry, and Kane all go out to celebrate. After a run-in with a new-age restaurant and waiter Shiloh (Spade), the crew ends up at Alex's Grandmother's house, where they find the ladies laughing hysterically as they watch Spanish television. They soon realize why; Grandma Lilly and her roommates drank tea made of Alex's marijuana.
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