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.

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 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.