Liza sends Caitlin off to college and struggles to weigh her feelings for both Josh and Charles.

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 pursue an erotica author writing under a pseudonym, and are shocked to discover their identity.

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

Liza finally makes her divorce official. Diana meets a hot stranger outside of work. Liza ends up in the hospital.

After Liza and Kelsey strike a deal for Colin's novel, an unexpected publicity hype leads to a bidding war. Emboldened by her therapist, Diana introduces herself to Richard, the therapist who works next door.

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

While facing an impasse with Josh, Liza draws closer to Charles at the Hamptons Book Fair. Kelsey feels erased from Colin's narrative.

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.