In the pilot episode, Aubrey Hassel (Taylor Kudalis), fresh from the "show me" state, arrives at Central High to meet nerdy girls Ocean, Piper, and Elly.
Grayson and Cam check out the new girl, Sadie and Reagan seek to find out if their gym teacher, Cal Jammer, is the 1980s adult film star of the same name.
Aubrey worries that her plans with Grayson might be more than just platonic. Ocean and Ellie argue over the meaning of art, while Mr. Duder and Ms. Tupelo warm up to each other in the break room.
Sadie recruits a reluctant Grayson to do her dirty work. The nerdy girls go on a hike with Cameron and Grayson, while the queen bees discuss their concern about Aubrey's increasing popularity.
Grayson approaches Cooper Davidson for the dirt he promised to Sadie. Piper reports on her audition for Sweeney Todd. Reagan decides she needs to take measures against Aubrey.
The girls head to the beach to celebrate the last days of summer. Aubrey finally talks to Cooper, infuriating Reagan. Grayson hits on Ms. Tupelo and confesses to Mila that he's been spying for Sadie.
Sarah and Casey finagle an invitation to Reagan's Halloween party. Mila reveals Sadie's betrayal to Reagan, leading to a tense standoff between the two. At the party, things go awry when Reagan spikes Sarah's drink.
Aubrey and Piper head to Boston to hang out in Harvard Yard and try Indian food. Grayson and Leyla clash over loyalties, meanwhile, in New York City on a visit to Strawberry Fields.
In the season finale, Aubrey and Piper visit Harvard Yard and dish on Aubrey's date over an Indian dinner. In New York City, Ocean visits John Lennon's grave and advises Leyla on how to talk to fain the group's trust.