Issa struggles in the aftermath of her breakup with Lawrence, while facing challenges at a new work assignment. Molly questions her worth at work, while Lawrence adjusts to his new living arrangement.

Issa tries to make sense of a cryptic encounter. Lawrence considers some crucial decisions. After being on the receiving end of some harsh truths, Molly plots to join the office "boys club." Issa and Frieda encounter a problematic vice principal.

Issa, Molly and Lawrence face choices affecting their work and personal lives, and consider what the future holds for them.

Issa tries to let go of some cherished mementos. At work, Frieda tries to help Issa get back in Joanne's good graces. Molly bonds with her new colleagues about an over-confident associate and vents to her therapist about her status at work.

Molly and Andrew embark on the ultimate double-date.

Issa considers doing Nathan a platonic favor. Meanwhile, both Dr. Rhonda and Andrew ask Molly to consider a different approach in dealing with people who've wronged her, and Issa extends a timely olive branch.