Issa tries to make sense of a cryptic encounter. Lawrence considers some crucial decisions. After being on the receiving end of some harsh truths, Molly plots to join the office "boys club." Issa and Frieda encounter a problematic vice principal.

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.

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

The girls take a weekend trip to celebrate Tiffany. Molly has trouble leaving her obsession with work behind.

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 is inspired while recruiting at a job fair with Frieda. Later, she treats Daniel to a thank-you dinner as she remains hopeful about their future. Molly starts her dream job at a black-owned law firm.

At a day party, Issa has her newfound confidence shaken. Molly has a blast from the past with childhood friend, Dro. A trip to the grocery store turns into a wild and crazy night for Lawrence.

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 maintains her roster but is met with disappointment as she finds herself without a car. Molly worries about an important friendship while embracing something new. Lawrence gets a rude awakening at work after pitching his app.

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

Tensions run high during Derek and Tiffany's dinner party. Molly rethinks her future after being forced to come to terms with her romantic realities. Issa tries to make things right with Frieda.

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 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 is mortified when a video of her profanity-laced rap at an open-mike night goes viral.

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.

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

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.

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 and Lawrence meet for drinks. Despite some initial awkwardness, the evening's events show just how deep their connection goes.

Issa needs moral support when her new project proves more complicated than she originally thought; Issa and Kelli press Molly to consider dating someone new; the girls attend Tiffany's baby shower and try to be helpful.

Trying to leave her troubles with Issa behind, Molly goes on a couples vacation to Mexico with Andrew and his brother and sister-in-law.

Still adjusting to newfound responsibilities, one of Issa's exes finds himself torn between two places, while an important woman in his life remains wary of his ability to be fully present back home.