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 gets advice from an unexpected source.

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

Issa struggles in the aftermath of her breakup with Lawrence, while facing challenges at a new work assignment. Molly questions her worth at work, while Lawrence adjusts to his new living arrangement.

Issa, Molly and Lawrence face choices affecting their work and personal lives, and consider what the future holds for them.

When Issa and Condola decide to confront the elephant in the room head-on, Lawrence gets uncomfortable; in search of a real connection, Molly struggles to get Andrew to open up during a date night.