Episodes: Series - Insecure S5 - 2021

• episode #1
• episode #2
• episode #3
• episode #4
• episode #5
• episode #6
• episode #7
• episode #8
• episode #9
• episode #10

Issa arrives at her college reunion in style as a member of the university's alumni committee, but feels doubtful about her new company, while Molly struggles with her breakup with Andrew, and her friendship with Issa remains strained and fragile.

Although her business is thriving, Issa struggles to establish herself, so she seeks the support of an old friend. Meanwhile, Molly is thinking about returning to the world of dating and entering into a romantic relationship.

Lawrence struggles to balance his career in San Francisco with his new responsibilities as a father in Los Angeles, but his partner Condola complains that he is neglecting his son's care, and intense disagreements and mistrust develop between them.

Issa and her new boyfriend face awkward situations at a work-related social event. As Molly juggles several suitors, Issa tries to defend herself against online backlash around her work.

Molly faces a family emergency, leaving her exhausted between caring for her loved ones, keeping up with her work, and focusing on her personal flaws. As a busy day passes, Issa and Nathan become closer than ever.

Distracted, Issa thinks about work and love while stumbling through the repercussions of a falling out with a colleague. While still struggling to cope with family issues, Molly finds comfort in an unexpected source.

Issa, Molly, Tiffany, and Kelli meet for a relaxing girls' night, and engage in candid conversations about their various personal struggles, insecurities, and the developments in their friendships. Tiff then announces that she is moving to Denver.

At a critical moment in her career, Issa is trying to choose two professional paths while simultaneously considering a major personal next step. Meanwhile, Molly spends a stressful day finalizing her parents' estate plan.

At Tiff's farewell party, Issa confronts her unresolved feelings, and Molly reveals her fears after a relaxing day with her new boyfriend.

As she and her friends try to be there for each other no matter what, Issa remembers the sacrifices she made to become the woman she is today.