Angie and Will dive headfirst into binge-watching a show called "JOUST!" together, but when Will starts to date someone new and ditches his TV-watching plans with Angie for time with his new love interest, Angie grows frustrated. Meanwhile, Poppy and Douglas bond over working on Rory's class president campaign until Poppy finds out about some of Douglas' shady campaign tactics.

Angie is sent into a tailspin when her long-absent ex-boyfriend Derek, Graham's father, suddenly appears on her doorstep. She asks Will and Miggy for help because, despite his faults, she can't resist Derek. Meanwhile, Douglas and Poppy try for a romantic second date.

After rent on the Winebrary goes up, the gang all chip in in their own ways to help solve Poppy's new financial problem, each learning a valuable lesson in the process.