The approaching Rawley Summer Cotillion inspires Will to approach the girl of his dreams, Caroline Busse, but when she already has a date for the dance, he invites Bella to go with him, although both their eyes are distracted by others. Meanwhile, Scout tries to make the most of his evening with Paige, and Hamilton and Jake reveal secrets in an intimate moment.

It's the weekend of the annual Rawley Regatta, the biggest race of the year for the crew team, but everyone's minds are distracted by the approaching Parent's Weekend. Scout is excited about introducing Bella to his dad, her real father, but she is more savvy to what the Senator's reaction may actually be. Meanwhile, Will reaches out to his own father, and Jake has to hide her new identity from her self-absorbed mother.

Bella, Will and Scout find themselves in the crazy position of having to outsmart an evil upperclassman, Ryder, sweet-talk a cop while driving a stolen car, and retrieve a confessional letter before it destroys their lives. Meanwhile, Hamilton and Jake secretly go on their first official date, but with Jake in a dress, the sexual roles are confused as Hamilton tries to wear the pants in the couple.