While Chester catches the attention of the school’s new guidance counselor, Greta learns she can’t sneak anything past her aunt. After secrets drive Nathan and his twin Naomi apart, he hopes Chester can turn his awful evening around.

Nathan's guilt over what happened with Naomi manifests in a very public declaration, while Chester, Riley and Greta sneak into an aquarium to get high. Later, Nathan once again forces Chester to play hero.

Chester angles to land himself in Sam's office, only to struggle with the guidance he's given. Megan grapples with the rapidly evolving world. Naomi and Arianna help their friend through her highly unconventional birth.

When school shuts down, Chester, Riley and Greta spend a blissful and intimate day together. With Chester distracted by a chance encounter with Sam, Greta and Riley explore a deeper level of their relationship.

The GSA embarks on their long-awaited trip to San Francisco. Greta and Riley navigate a new awkwardness, Nathan and Naomi turn a fun game into a merciless sibling takedown, and Sam moves his questions for Chester offline.

On the way to San Francisco, Nathan and Arianna are forced to navigate an awkward truth, Riley and Greta struggle to connect, and Chester’s admission to Sam sends them both spiraling.

Chester recovers from his misfire with Sam, Naomi inadvertently shares a private video with her entire family, and Delilah leans on her friends for help making the most important decision of her life.

Back at school, Greta and Riley encounter residual weirdness from their trip to San Francisco, and Cooper makes French class way more interesting for Naomi... and Delilah. After an uncharacteristically nervous Chester braves his first date with Bo, Nathan makes him an offer he can't refuse.

As Chester plays the part of his "boyfriend," Nathan returns the favor with some unsolicited dating assistance. Meanwhile, Greta finds herself stuck between family obligations and an exciting new connection with Luz, and Delilah keeps Riley close for an unconventional date with Cooper.

Struggling to manage dynamics at home and at school, Riley pours herself into searching for a job, discovering support systems in Sam and Ana. Greta and Luz establish boundaries, while Chester and Bo find a spark. Later, Greta's family dinner is full of surprises and secrets.

Drowning in excessive male energy, Arianna hosts a girls-only sleepover for Naomi and Delilah. As they work to cast the negativity out of their lives, a potentially devastating secret also helps inspire a solution for Delilah and Naomi's romantic dilemma – much to Arianna's chagrin.

After Nathan tries rescheduling their mother-son date night, Megan begrudgingly joins him at a fundraiser for queer youth, where she struggles with revelations about both her kids. Meanwhile, her unexpected arrival forces Chester to divulge the details of his arrangement with Nathan to Bo, and Greta's indecisiveness finally catches up with her.

After her father delivers a crushing family update, a sleep-deprived Riley tries to avoid Sam's concern, searches for an MIA Chester, and bumps heads with Greta and Ana. Meanwhile, Naomi's dental procedure wreaks havoc on more than just her mouth.

Mark's Valentine's Day party for the teens has an unexpected effect on his wife. After untangling their relationship from Nathan, Chester and Bo land in Megan's crosshairs. Riley and Greta work up the courage to level with each other.

Valentine's Day puts love, truth, and friendships to the test as Riley struggles to put out the overwhelming fires around her, Cooper pushes Delilah towards honesty, and Chester and Nathan's relationship comes full circle.