In the wake of her 29th birthday, Issa reflects on her life and relationship choices.

Issa struggles with her feelings about Lawrence, work, and her life.

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.