Liza rallies the Empirical team to save her hometown bookstore from closure. Kelsey dips her toe back into the dating world.

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.

Kelsey dates a seemingly perfect guy, but Liza and Lauren think it’s too soon. At a party of doctors, Josh puts his relationship with Liza under the microscope.

Liza and Kelsey try to preserve their author’s anonymity, but a women’s erotica event threatens to expose the truth.

Liza returns from the Hamptons and has to deal with the aftermath. A famous life coach, whose book Empirical is pursuing, forces Liza to face some hard truths.

Liza deals with the aftermath of coming clean with Kelsey, and Charles tests their synchronicity. Kelsey and Josh become unlikely allies.

Liza faces further fallout with Kelsey, who is infuriated by Liza's lack of millennial know-how.

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

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.