Liza is back at Empirical trying to maintain her millennial masquerade and process her feelings for Charles. Meanwhile, Josh is pushing to rekindle their relationship, setting her work and personal lives on a collision course.
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.
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 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.