17-годишната Рю се връща вкъщи, след като е била в клиника за лечение на наркозависими, но няма намерение да остане „чиста“. На парти в дома на Маккей тя се запознава с Джулс, която е нова в града. Нейт започва да разбира Маккей, когато Маккей проявява интерес към Каси. Нейт и Мади отново са скъсали и правят всичко възможно да накарат другия да ревнува. По същото време Кат е притисната да направи нещо.

On the first day of school, Rue's excited about her new friend, Jules, but struggles to put the past behind her and gets into trouble at Fezco's. Nate becomes obsessed with Maddy's hookup, Tyler, while trying to get back together with Maddy. Kat finds out that a video of her has surfaced online. McKay takes the stress of college out on Cassie.

Kat decides to try camming and has her first session. Jules starts falling for a boy online and asks Rue to help her take some nudes. Maddy finds something odd on Nate's phone. Cassie and McKay spend the weekend at his school and go to a party at the frat he's rushing. Rue is confronted about her lies at NA.

Rue tries to get clean for Jules and chaperones Gia at the carnival. Jules encounters Cal with his family. Cassie and Maddy, annoyed at their boyfriends, decide to do molly together. Kat hangs out with Ethan until she misreads a situation. Nate reveals who he really is.

In the aftermath of the carnival, Maddy and Nate are forced to deal with a police investigation. Jules begins to feel pressured by her role in Rue's sobriety. Kat ignores a confused Ethan and embraces her new lifestyle. Cassie ries to distance herself from Daniel and focus on her relationship with McKay. Cal worries about how his actions have affected his sons.

On Halloween, Rue worries about her reliance on Jules, while Jules starts exhibiting concerning behavior. McKay questions his future in football. After a weird night with McKay, Cassie spends time with Daniel. Business is booming for Kat as she continues to push Ethan away. Nate comes up with a plan to get his life back on track.

Rue gets depressed and watches 22 straight episodes of a British reality show.​ Jules goes to visit an old friend. Cassie looks for advice in the aftermath of Halloween night.

In the Season One Finale, it's the winter formal at East Highland.

Rue and Jules cross paths for the first time since Christmas as East Highland rings in the new year.

As the semester kicks off, Jules questions Rue and Elliot's new friendship. While Cal hunts for answers, Nate makes a tough decision. The lines between fantasy and reality begin to blur as Kat ponders her relationship, and Maddy contemplates the decision to end hers.

Rue pursues a new business venture, Cassie settles into a routine, and Cal finds a target.

At Maddy’s birthday party, relationships are celebrated and questioned. Meanwhile, Jules turns to Elliot for advice and Cal takes a trip down memory lane.

Fate has a way of catching up with those who try to outrun it.

As relationships with mothers are tested, Rue tries to recover. Meanwhile, Lexi questions the possible backlash from her play, and Nate celebrates his newfound freedom.

Art imitates life as the East Highland crew watches their complicated dynamics reflected in Lexi's long-awaited play. Meanwhile, Fezco gets ready to attend.

As the show goes on, fragments of memories collide with the present and future.