In the wake of her 29th birthday, Issa Dee reconsiders her dead-end relationship with Lawrence, her live-in boyfriend. Meanwhile, Issa's best friend, Molly, mourns her singledom and the state of her lady parts. Later, Issa uses an open-mic night as an excuse to reconnect with an ex. Written by HBO

After the unexpected events of the previous night, Issa tries to decide what to do about Lawrence, while sticking to her plan to embrace a bolder side of herself. Molly treats herself to a fancy day and goes on a promising date. Lawrence gets advice from an unexpected source. Written by HBO

Issa and Lawrence try to move past their issues at home; Issa deals with doubts from her colleagues; Lawrence gets a reality check from a headhunter; Molly introduces Jared to her friends.

Issa turns to Daniel for help during Career Day; Molly finds herself in a tough position at work; Lawrence bonds with a surprising confidante.

Issa searches for a way to get her open mic video taken down; Issa reconnects with Daniel; Lawrence faces questions about his future with Issa; Molly invites her perfect guy to a coworkers engagement party.

Issa tries to keep things together while hiding her guilt; Lawrence gets serious about his commitment to Issa; Molly embraces a new relationship.

A girls' trip finds Issa and Molly in close quarters, while Lawrence vents with his boys.