Josh and Liza's relationship becomes strained after he is included in a New York Times profile.

Liza has to bridge millennial divides in the workplace and in her personal life when Empirical’s new investor tasks her with signing YouTube stars.

Liza and Josh's future together is thrown into question after having opposing reactions to a near miss.

Liza and Kelsey dive back into the dating pool and quickly discover it's much more complicated than they'd hoped.

Liza pursues a new relationship as Kelsey revisits an old one. Diana learns the truth about Richard. Lauren encourages Josh to follow his heart.

Liza gets to know a charming journalist and confronts Charles, Diana agrees to a date with a familiar face, and Josh wants a reset.

It's Christmas in New York! Liza must attend a party with Caitlin and her ex-husband, Kelsey finds herself caught up in a web of her own making as she struggles to keep both her relationships under wraps, and Charles glimpses Liza’s other life.

Change is in the air at Empirical, and Liza considers her options. Meanwhile, Kelsey receives surprising news, and Charles finds a solution.

Liza and Charles' romance heats up, but Liza suspects he's keeping something from her. Millennial gets the scoop on a tell-all from acquitted murderer Audrey Colbert. Kelsey feels undermined by Quinn.

Millennial's deal with a youth clothing company falls into jeopardy after Liza's age is revealed, Maggie gets a crush on a male artist, and Quinn stages a publicity stunt.

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.

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.