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 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 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.

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.