Despite her now thriving business, Issa struggles to find her footing and turns to an old friend for support. Meanwhile, Molly contemplates jumping back into the dating pool.

Pulling up to her ten-year college reunion in style as an alumni panelist, Issa's self-doubt quickly surfaces, while Molly – still reeling from her breakup – struggles to get out of her own head. As the crew takes the opportunity to reflect, old wounds remain tender.

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.

A long overdue girls' night filled with self-reflection and real talk puts things into perspective for Issa and her friends.

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.

At a crossroads in her career, Issa weighs the pros and cons of two viable paths while simultaneously contemplating an important personal next step. Meanwhile, with help from Kelli, Molly spends an overwhelming day getting her parents' estate plan in order.

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 her new man tread awkward waters at a work-related social event. Meanwhile, Molly juggles multiple suitors, and Issa plays defense against online attacks about her business.

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.

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 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 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.

Molly and Andrew embark on the ultimate double-date.

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.

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.

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 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.

Issa tries to concentrate on her business plan, but is driven to distraction; Molly steps out of her comfort zone in her love life.

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

Issa and Condola prep for a mixer to promote the block party. Molly has feelings for Andrew.

The girls get together to help Tiffany with her new baby girl. Later, Issa struggles to finalize key details for the block party and turns to Molly to leverage Andrew's connections.

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.

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.

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