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Insecure

Season 5 2021
TV-MA

  • 2021-10-25T02:00:00Z on HBO
  • 30m
  • 4h 43m (10 episodes)
  • United States
  • English
  • Comedy, Drama
Follows the awkward experiences and racy tribulations of a modern-day African-American woman.

10 episodes

Season Premiere

2021-10-25T02:00:00Z

5x01 Reunited, Okay?!

Season Premiere

5x01 Reunited, Okay?!

  • 2021-10-25T02:00:00Z32m

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.

2021-11-01T02:00:00Z

5x02 Growth, Okay?!

5x02 Growth, Okay?!

  • 2021-11-01T02:00:00Z26m

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.

2021-11-08T03:00:00Z

5x03 Pressure, Okay?!

5x03 Pressure, Okay?!

  • 2021-11-08T03:00:00Z27m

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.

2021-11-15T03:00:00Z

5x04 Faulty, Okay?!

5x04 Faulty, Okay?!

  • 2021-11-15T03:00:00Z27m

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.

2021-11-22T03:00:00Z

5x05 Surviving, Okay?!

5x05 Surviving, Okay?!

  • 2021-11-22T03:00:00Z24m

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.

2021-11-29T03:00:00Z

5x06 Tired, Okay?!

5x06 Tired, Okay?!

  • 2021-11-29T03:00:00Z26m

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.

2021-12-06T03:00:00Z

5x07 Chillin', Okay?!

5x07 Chillin', Okay?!

  • 2021-12-06T03:00:00Z27m

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

2021-12-13T03:00:00Z

5x08 Choices, Okay?!

5x08 Choices, Okay?!

  • 2021-12-13T03:00:00Z27m

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.

2021-12-20T03:00:00Z

5x09 Out, Okay?!

5x09 Out, Okay?!

  • 2021-12-20T03:00:00Z28m

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.

Season Finale

2021-12-27T03:00:00Z

5x10 Everything Gonna Be, Okay?!

Season Finale

5x10 Everything Gonna Be, Okay?!

  • 2021-12-27T03:00:00Z39m

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.

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