In the wake of her 29th birthday, Issa Dee reconsiders her dead-end relationship with her live-in boyfriend. 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.

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

Although things are better with Lawrence, Issa turns to Daniel for help during Career Day. Molly finds herself in a tough position when a partner asks her to give Rasheeda a talking-to. Facing disappointment at his new job, Lawrence bonds with a surprising confidante.

Issa searches for a way to get her open mic video taken down and finds herself reconnecting with Daniel during a trip to his studio. Lawrence faces questions about his future with Issa. Molly invites her 'perfect guy' Chris to her co-worker's engagement party.

Issa tries to keep things together while hiding her guilt, as Lawrence doubles down on his commitment to her. Molly embraces a new relationship, but after learning more than she wants to about her new beau's past, struggles to focus on their future.

As Issa prepares for an important work fundraiser, her plan to keep focused gets derailed. Lawrence considers a career opportunity, and Molly runs into an old friend with a new outlook.

The lingering tension between Molly and Issa threatens to resurface during a girls' trip. Lawrence, meanwhile, reconnects with his friends.