Issa struggles after the break with Lawrence and difficulties with a new task at work. Molly doubts her worth at work, and Lawrence adapts to his new housing situation.

Issa tries to make sense of a cryptic encounter; Lawrence considers crucial decisions; after receiving some harsh truths, Molly plots to join the office "boys club"; Issa and Freida encounter a problematic vice principal.

A sexually frustrated Issa explores a new outlook on dating; on a girl's night out, Molly meets a promising new guy; Lawrence's new work friends test his commitment.

Issa's confidence is shaken; Molly hangs with a childhood friend; Lawrence has a wild and crazy night.

Issa explores casual relationships; Molly learns some new truths; Lawrence stumbles on news.

Tensions run high during Derek and Tiffany's dinner party. Molly rethinks her future after being forced to come to terms with her romantic realities. Issa tries to make things right with Frieda.

Over the course of one pivotal month, Issa, Molly, and Lawrence face choices impacting their work and personal lives, with each considering whether to embrace a new future or look back to the past.