Issa struggles in the aftermath of her breakup with Lawrence, while facing challenges at a new work assignment, as Season 2 begins. Meanwhile, Molly questions her worth at work; and Lawrence adjusts to his new living arrangement.

A cryptic encounter tests Issa's interpretive skills; Lawrence mulls some important decisions; Molly plots to join the office "boys club" after being on the receiving end of a few harsh truths; Issa and Frieda deal with a difficult vice principal.

Issa's sexual frustration prompts her to reassess her dating outlook; Molly meets a potential beau on a girls' night out; Lawrence's new work friends test his commitment.

Issa's newfound confidence is shaken at a day party; Molly has an eventful reunion with a childhood friend; Lawrence's trip to the grocery store turns into a wild and crazy night.

Issa attempts to build a roster and butts heads with Frieda at a work retreat. Molly's day takes an unexpected turn at her parents' vow renewal ceremony. Lawrence stumbles upon some news about Issa.

Issa maintains her roster but is met with disappointment as she finds herself without a car. Molly worries about an important friendship while embracing something new. Lawrence gets a rude awakening at work after pitching his app.

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 affecting their work and personal lives, with each considering whether to embrace a new future or look back to the past.