Insecure

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.

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 searches for advice and finds it from an unexpected source.

Issa and Lawrence try to move past their issues at home, as Issa deals with her colleagues' doubts and Lawrence gets a reality check from a head hunter. Molly introduces Jared to her friends, and later, struggles to give a new summer associate at work some words of wisdom.

Despite things being better than ever with Lawrence, Issa turns to Daniel for help during Career Day. Molly finds herself in a tough position when she's asked by a partner to give Rasheeda a talking to. Facing disappointment at his new job, Lawrence bonds with a surprising confidante.

A mortified Issa searches for a solution to a newfound problem. Lawrence faces questions about his future. Molly invites a 'perfect guy' to her co-worker's engagement party, while attempting to navigate her 'friendship' with Jared.

Issa tries to keep things together, as Lawrence doubles down on his commitment. Molly embraces a new relationship, but struggles to focus on the future.