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 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.

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

Issa tries to let go of some cherished mementos. At work, Frieda tries to help Issa get back in Joanne's good graces. Molly bonds with her new colleagues about an over-confident associate and vents to her therapist about her status at work.

As she and her friends try to make time for each other no matter what, Issa looks back on all it took to get to where she is today.