Insecure

After her 29th birthday, Issa Dee reconsiders her relationship with her live-in boyfriend, Lawrence; Issa's best friend, Molly, laments being single; Issa reconnects with an ex at an open-mic night.

Issa attempts to make a decision 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 some advice.

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 head hunter; 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 coworker's 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.