Insecure

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 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.

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 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 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.

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 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.

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

While Issa and Condola continue planning for the Block Party, both are made aware that Condola is seeing Lawrence. Meanwhile, Molly may be developing feelings for Andrew, who wants to keep his options open.

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 and Molly prepare to spend Thanksgiving with their families while Lawrence makes his way to Condola's "Friendsgiving." But as the night progresses, truths surface for each party that no one was expecting.

When Issa has a block party crisis, she turns to a reluctant Molly for help.

Issa works around the clock to ensure the event goes off without a hitch.

At her ten-year college reunion, Issa's self doubt quickly surfaces, while Molly struggles to get out of her own head.

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.

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.

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.

A family emergency finds Molly stretched thin between taking care of loved ones, staying on top of work, and zeroing in on her own perceived shortcomings. As a hectic day unfolds, Issa and her new man grow closer than ever.