Jacqueline, in an attempt to see if her mother notices her, enrolls at Rawley Academy and presents herself as Jake. Things get complicated when she develops feelings for Hamilton, the dean's son. Hamilton begins to wonder if he is gay as he realizes he has feelings for Jake.
The rowing team's cox "Jake" Pratt makes a profound impression on Hamilton. Hamilton is surprised by this and starts to question his own sexual orientation.
Hamilton lets Jake know that he's not into guys. Jake's bike is confiscated by the groundskeeper and Hamilton offers to help get it back.
Kiss and Tell
Lena, an LA resident visiting Rawley Academy, hears about the drive-in and invites Jake to join her and Hamilton.
Hamilton and Jake agree to go alone together to the Ball, an agreement which is broken when Lena asks Hamilton to go with her. Jake reveals to Hamilton that she is in fact a girl and they kiss.
Winning Isn't Everything
Jake's mother makes an unexpected visit for parents' weekend and the regatta, leading to Jake and Hamilton having to try to keep Jake's secret from her.
Jake and Hamilton go on a date and are confused as to who should pick up the tab or ride the "bitch pad" of Jake's bike. They fight and then make up later.
Hamilton suggests moving in with Jake so that they can spend more time together. Jake thinks it's moving too fast and says no.
Will Bella Scout Her Mom?
Jake's masquerade comes to an abrupt halt and she and Hamilton travel with Bella and the others. Jake then leaves for New York.