The BEST episodes of Insecure season 5

Every episode of Insecure season 5, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Insecure season 5!

Follows the awkward experiences and racy tribulations of a modern-day African-American woman. Issa and Molly, these best friends must deal with their own real-life flaws as they attempt to navigate different worlds and cope with an endless series of uncomfortable everyday experiences.

Last Updated: 11/13/2024Network: HBOStatus: Ended
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Everything Gonna Be, Okay?!
star
8.18
135 votes

#1 - Everything Gonna Be, Okay?!

Season 5 - Episode 10 - Aired 12/26/2021

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.

Directors: Prentice Penny
Writer: Issa Rae
Watch Now:AmazonApple TV
Chillin’, Okay?!
star
8.11
149 votes

#2 - Chillin’, Okay?!

Season 5 - Episode 7 - Aired 12/5/2021

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

Directors: Amy Aniobi
Writer: Fran Richter
Watch Now:AmazonApple TV
Out, Okay?!
star
8.02
120 votes

#3 - Out, Okay?!

Season 5 - Episode 9 - Aired 12/19/2021

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.

Directors: Prentice Penny
Watch Now:AmazonApple TV
Surviving, Okay?!
star
7.86
141 votes

#4 - Surviving, Okay?!

Season 5 - Episode 5 - Aired 11/21/2021

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.

Directors: Kerry Washington
Watch Now:AmazonApple TV
Tired, Okay?!
star
7.74
145 votes

#5 - Tired, Okay?!

Season 5 - Episode 6 - Aired 11/28/2021

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.

Directors: Natasha Rothwell
Watch Now:AmazonApple TV
Reunited, Okay?!
star
7.74
151 votes

#6 - Reunited, Okay?!

Season 5 - Episode 1 - Aired 10/24/2021

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.

Directors: Melina Matsoukas
Writer: Amy Aniobi
Watch Now:AmazonApple TV
Growth, Okay?!
star
7.69
160 votes

#7 - Growth, Okay?!

Season 5 - Episode 2 - Aired 10/31/2021

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.

Directors: Maurice Marable
Watch Now:AmazonApple TV
Faulty, Okay?!
star
7.62
155 votes

#8 - Faulty, Okay?!

Season 5 - Episode 4 - Aired 11/14/2021

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.

Directors: Maurice Marable
Watch Now:AmazonApple TV
Choices, Okay?!
star
7.59
128 votes

#9 - Choices, Okay?!

Season 5 - Episode 8 - Aired 12/12/2021

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.

Directors: Kevin Bray
Watch Now:AmazonApple TV
Pressure, Okay?!
star
7.59
150 votes

#10 - Pressure, Okay?!

Season 5 - Episode 3 - Aired 11/7/2021

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.

Directors: Ava Berkofsky
Writer: Jason Lew
Watch Now:AmazonApple TV