When Tessa gets her driver's license, Dalia hires her to drive her around to stalk her crush, Scott Strauss. As a result Tessa realizes that she and Scott might have feelings for each other. Meanwhile George and Noah's relationship is put to the test when George decides he wants to join the local country club.
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.
After winning a weekend trip to Atlantic City in a raffle, George takes Noah, Fred, Alex, and Tom for a "guy's night out". Once there, Fred has to face his gambling addiction, and George runs into Dallas' husband. Meanwhile, Tessa uses the time home alone to get to know Scott Strauss better.
George finds it difficult to talk to Tessa about sex after he finds a box of condoms in her room, so he seeks advice from her peers. While sending out the laundry, Dallas makes a discovery that leads to a life change.
When Tessa realizes that she's failing gym class, she decides to run for student body president in hopes of changing Chatswin High's obsession with sports. During the election, Lisa steps in as Tessa's campaign manager against Kenzie and Kaitlyn. Meanwhile, Ryan is injured during a wrestling match and finds himself mourned by his family, and George takes Ryan under his wing and introduces him to people who have moved forward from setbacks.
When Jill turns to the newly single Dallas for inspiration and support, her marriage to Noah goes on the rocks. Meanwhile Dallas begins spending a lot of time with her hot younger boyfriend, Yoni, which causes tension with George, and Dalia befriends Lisa to get back at Tessa for dating Scott Strauss -- so Tessa decides to take action and recruits Kimantha to make Dalia jealous.
When Fred and Sheila strike up a croquet match with Dallas and George, Fred misreads Sheila's interest in George. Fred tells George that Sheila is fantasizing about him and asks him to seduce her. Meanwhile Tessa desperately wants to impress the new poetry teacher, Ms. Evans, but she seems to prefer Dalia's prose.
When George picks Tessa up late from school she decides to get a job working for Dallas in order to buy her own wheels. Meanwhile Dallas invites her sorority sisters to stay with her in order to celebrate the opening of her store, A Crystal Cup of Crystals; however her rival sorority sister, Tulsa, decides to crash the party.