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.

Although things are better than ever 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 is mortified when a video of her profanity-laced rap at an open-mike night goes viral.

Issa preps for a fund-raiser, but has trouble staying focused. Meanwhile, Lawrence mulls a job opportunity; and Molly learns something new from an old friend.