Chester's style choices catch the attention of the school's new guidance counselor Sam, who becomes determined to help him open up. Meanwhile, Greta navigates the stark difference between her mother and aunt's parenting styles, and after secrets drive a wedge between Nathan and his twin sister Naomi, he shows up at Riley's party hoping that Chester can turn his miserable evening around.

When the chaos of Club Fair Day is unexpectedly interrupted, the teens are forced to reckon with some difficult truths. Later, just as Naomi decides to take her relationship with Jack to the next level, she makes a startling discovery.

Nathan and Naomi are forced to play nice at their older sister's wedding rehearsal dinner – but the truth seeps out during Nathan's toast. Meanwhile, Chester, Greta, and Riley sneak into an aquarium to get away from their problems and get high instead, and later, Nathan once again forces Chester to play hero.

Chester gets creative in his methods for landing in Sam's office, only to be given advice he may not be ready to absorb. Megan grapples with the rapidly evolving world and what her acceptance might mean for the happiness of her children. After a highly stressful labor, Naomi and Arianna help their friend through her unconventional birth.

After nearby fires force the school to close, Chester, Greta, and Riley spend the day together, growing closer and sharing intimate details about their personal lives. With Chester distracted by an unexpected encounter with Sam, Greta and Riley explore new levels of their relationship.

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