Liza sends Caitlin off to college and struggles with her feelings for both Josh and Charles.
Liza's identity is threatened by Thad's laptop and Kelsey learning the truth; a Silicon Valley billionaire invests in Empirical.
Liza rallies the Empirical team to save her hometown bookstore from closing; Kelsey rejoins the dating world.
Empirical's new investor tasks Liza with signing YouTube stars, forcing her to bridge millennial divides in the workplace and in her personal life.
Kelsey dates a seemingly perfect guy, but Liza and Lauren are concerned; Josh puts his relationship with Liza under the microscope at a party of doctors.
Liza and Kelsey investigate an erotica author writing under a pseudonym and are shocked by what they find.
Liza and Kelsey try to protect their author's anonymity, but a women's erotica event may reveal 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.