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.

Issa tries to hide her guilt from Lawrence, who reiterates his love for her. Meanwhile, Molly dives into a new romance, but has second thoughts about the future after learning unsavory details about her new boyfriend's past.

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.

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.

A sexually frustrated Issa explores a new dating outlook. On a girls' night out, Molly meets a promising new guy. Lawrence's commitment is tested by his new work friends.

Issa attempts to build a roster and butts heads with Frieda at a work retreat. Molly's day takes an unexpected turn at her parents' vow renewal ceremony. Lawrence stumbles upon some news about Issa.

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

Issa crashes on Daniel’s couch and tries to save up extra cash. Molly returns from a beach vacation with renewed determination to maintain boundaries in her life.

Issa gets advice from Kelli about her financial situation and plays wingwoman as Daniel tries to make a music-industry connection.