When Tessa overhears George break up with his girlfriend, Zoe, on Skype, she blames herself for his failed relationship and decides that she's going to get them back together. Unbeknownst to her, though, George is really enamored with Tessa's cute art teacher, Aimee. He admits to Mr. Wolfe that he's over dating crazy city women, and that he's looking for love in the burbs. George decides to embrace the holiday spirit with a tree trimming party complete with ex-girlfriend, potential new girlfriend and the Royces, and he soon finds himself under the mistletoe with a special someone.

When Tessa is asked to show new guy Josh Sherman around school, she becomes convinced that he's gay, when in fact he's an undercover narcotics officer. Lisa becomes deeply infatuated with Josh, and Tessa inadvertly convinces Mr. Wolfe to make special announcement to the student body. Meanwhile George re-evaluates his relationship with Dallas.