As Diana sets out on her honeymoon, Liza considers Charles's proposal. Kelsey turns Quinn down, but some speed bumps in her personal and professional life make Kelsey doubt herself. Lauren's 30th is out of this world.

Liza tries to settle into the next chapter of her personal life. Liza and Kelsey dig deep to win over Fupa Grünhoff, a teenage climate change activist.

Liza travels to Montauk to help a sexy pro surfer with his memoir. She comes back to the office refreshed. An unexpected adventure with Quinn leaves Kelsey questioning her career choices. Josh's new love interest gets loud.

After Quinn's new romance goes public, Liza decides to fact-check her manuscript. Maggie gets an exciting new job offer and love interest. Sparks fly between Liza and someone from her old life.

Liza and Kelsey start an underground event called Inkubator. Liza debates telling Charles about Quinn's true motives. Maggie’s first class lands her an invite to dinner at the dean’s.

After an Empirical author dies, Charles reconnects with the widow who was the real-life inspiration for his novel, The Miseducation of Henry Cane. Maggie teaches a class on her past art and is confronted with a big problem.

When Caitlin needs help with a Vassar event, Liza is forced to turn to an inconvenient source: Quinn. Kelsey is unhappy with her time in the spotlight and tries to find a way out of it. Maggie gets cancelled.

Liza and Charles work closely together to land a married writing duo; after Redmond calls her out, Kelsey takes drastic measures to keep an author she nurtured at her literary salon; Kelsey's personal life gets complicated.

Maggie debuts a new art show at an unconventional venue; Clare helps Kelsey at work, as their dating lives become intertwined; Liza convinces Charles to come to her literary salon where a major talent reads.

Things seem to be warming up between Liza and Charles, but a piece of intel and an exotic trip make Liza feel iced out; Kelsey moves into a new apartment, and Lauren throws her a housewarming party with a surprising ending.

Charles and Liza make amends and promise not to lie anymore, but Kelsey's plans force Liza to withhold the truth. Lauren plans a romantic reunion. Sparks fly between Maggie and an enemy-turned-friend.