11. Mean Teacher

Complete story — includes the ending

Drake wants to break up with his latest girlfriend Kelly ( Chelsea Brummet ), due to her habit of obnoxiously laughing in inappropriate situations. However, once Drake finds out that Mrs. Hayfer ( Julia Duffy ), their school English teacher who hates Drake, is Kelly's mother, Mrs. Hayfer threatens to send Drake to summer school should he break up with Kelly. Josh suggests that Drake should make Kelly break up with him instead, so Drake attempts to do so by acting repulsive during a dinner date, however his plan backfires. Meanwhile, Josh begins wearing a rather ugly shirt, resulting in good things consistently happening to him, such as: Receiving a perfect score on a school assignment, being handed an expensive watch and ring by a feuding couple, being gifted a classmate's entire video game collection, successfully avoiding Megan's pranks, and having Kelly set him up on a date with a teen model who loves magic and video games. Sometime later, Drake, now completely fed up with Kelly's incessant laughter, demands to wear Josh's lucky shirt to their double date. However, Josh refuses, leading to a fight that rips the sleeves off the shirt. Drake wears the sleeves and Josh the torso, however neither date goes well. Josh then agrees to let Drake wear the whole shirt until Kelly breaks up with him, then give the shirt back to Josh for the rest of the night. Sure enough, Kelly breaks up with Drake, much to his delight, and Josh's date takes a liking to him, even kissing him. The next day, the boys find that the shirt is gone, having been donated to Goodwill by Audrey on the suggestion of Megan. Initially angry, the boys overcome it by convincing themselves that the shirt was not lucky. During the end credits, a hobo wins the lottery jackpot while wearing the shirt.