Insecure: Season 5

2021 · 10 episodes · ★ 2.0

What Season 5 of Insecure

Molly and Issa patch up their relationship, but the four friends are still striving to make their careers and love lives turn out the way they want.

10episodes

Oct 24, 2021aired

Dec 26, 2021final episode

4.9 hrtotal runtime

Season 5 Episodes

5x01 Reunited, Okay?!
Oct 24, 2021 · 32 min · ★ 1.9
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.
Directing: Melina Matsoukas · Writing: Amy Aniobi · Starring: Amanda Seales, Wade Allain-Marcus, Diallo Riddle, Taja V. Simpson
5x02 Growth, Okay?!
Oct 31, 2021 · 29 min · ★ 1.8
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.
Directing: Maurice Marable · Writing: Phil Augusta Jackson · Starring: Kendrick Sampson, Sahana Srinivasan, Courtney Taylor, L. Scott Caldwell
5x03 Pressure, Okay?!
Nov 7, 2021 · 28 min · ★ 2.1
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.
Directing: Ava Berkofsky · Writing: Jason Lew · Starring: Amanda Seales, Neil Brown Jr., Wade Allain-Marcus, Kristofer Gordon
5x04 Faulty, Okay?!
Nov 14, 2021 · 28 min · ★ 1.9
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.
Directing: Maurice Marable · Writing: Syreeta Singleton · Starring: Kendrick Sampson, Courtney Taylor, Brittney Ayona Clemons, Curtis Hamilton
5x05 Surviving, Okay?!
Nov 21, 2021 · 25 min · ★ 2.0
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.
Directing: Kerry Washington · Writing: Laura Kittrell · Starring: Kendrick Sampson, L. Scott Caldwell, Gregg Daniel, Malcolm David Kelley
5x06 Tired, Okay?!
Nov 28, 2021 · 27 min · ★ 2.0
A distracted Issa mulls over work and love as she stumbles through the consequences of her falling out with a colleague. Meanwhile, Molly - still struggling to cope with family matters - finds comfort in an unlikely source.
Directing: Natasha Rothwell · Writing: Grace Edwards · Starring: Kendrick Sampson, Courtney Taylor, L. Scott Caldwell, Gregg Daniel
5x07 Chillin', Okay?!
Dec 5, 2021 · 29 min · ★ 2.0
A long overdue girls' night filled with self-reflection and real talk puts things into perspective for Issa and her friends.
Directing: Amy Aniobi · Writing: Fran Richter · Starring: Amanda Seales, Kendrick Sampson, Elle Lorraine, Christina Elmore
5x08 Choices, Okay?!
Dec 12, 2021 · 28 min · ★ 2.2
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.
Directing: Kevin Bray · Writing: Eli Wilson Pelton · Starring: Kendrick Sampson, Sahana Srinivasan, Courtney Taylor, Ty Dolla $ign
5x09 Out, Okay?!
Dec 19, 2021 · 29 min · ★ 2.0
At a friend's going away party, Issa navigates unresolved feelings. After spending the day letting loose with her new man, Molly opens up about her fears.
Directing: Prentice Penny · Writing: Prentice Penny · Starring: Amanda Seales, Sarunas J. Jackson, Kendrick Sampson, Neil Brown Jr.
5x10 Everything Gonna Be, Okay?! Season Finale
Dec 26, 2021 · 41 min · ★ 2.1
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.
Directing: Prentice Penny · Writing: Issa Rae · Starring: Amanda Seales, Lisa Joyce, Sujata Day, Kendrick Sampson