The WORST episodes of Insecure

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

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: 8/22/2026Network: HBOStatus: Ended
Lowkey Lost
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#1 - Lowkey Lost

Season 4 - Episode 10 - Aired 6/14/2020

Molly takes Andrew to a work function and they struggle to see eye to eye. Issa continues to search for happiness. The girls get a distressing call about a friend.

Directors: Prentice Penny
Ghost-Like
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#2 - Ghost-Like

Season 3 - Episode 8 - Aired 9/30/2018

After facing numerous obstacles, Issa gets discouraged about her project, while Molly helps give Issa a drama-free 30th birthday.

Directors: Regina King
Lowkey Feelin' Myself
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#3 - Lowkey Feelin' Myself

Season 4 - Episode 1 - Aired 4/12/2020

With Condola's guidance, Issa prepares for a mixer in her courtyard to pitch the block party to potential sponsors – but tensions rise when they discover a mutual connection. Molly begins to develop unexpected feelings for Andrew.

Directors: Kevin Bray
Writer: Issa Rae
Lowkey Distant
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#4 - Lowkey Distant

Season 4 - Episode 2 - Aired 4/19/2020

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 carefully architected date night.

Directors: Thembi Banks
Writer: Amy Aniobi
Lowkey Thankful
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#5 - Lowkey Thankful

Season 4 - Episode 3 - Aired 4/26/2020

While Molly's family celebrates Thanksgiving together, Issa and Ahmal decide to do their own thing. Meanwhile, when Lawrence joins Friendsgiving at Condola's house, the new couple breaks some awkward ground.

Directors: Mark Sadlek
Lowkey Losin' It
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#6 - Lowkey Losin' It

Season 4 - Episode 4 - Aired 5/3/2020

The girls get together to help Tiffany with her new baby girl. Later, Issa struggles to finalize key details for the block party and turns to Molly to leverage Andrew's connections.

Directors: Nijla Mu'min
Lowkey Movin' On
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#7 - Lowkey Movin' On

Season 4 - Episode 5 - Aired 5/10/2020

With the block party finally here, Issa is determined to deliver a memorable event, despite some surprises. Meanwhile, Tiffany enjoys a break from her baby, Kelli entertains a gullible new boo, and Molly attempts to put a grudge on hold.

Directors: Stella Meghie
Lowkey Done
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#8 - Lowkey Done

Season 4 - Episode 6 - Aired 5/17/2020

In need of some positive vibes after the block party, Issa goes out of her way to do good for random people across L.A., eventually turning to an unlikely source for comfort. Meanwhile, Kelli urges her friends to reconcile.

Directors: Lacey Duke
Writer: Fran Richter
Lowkey Trippin'
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#9 - Lowkey Trippin'

Season 4 - Episode 7 - Aired 5/24/2020

Molly and Andrew take off for their first couples’ vacation with Andrew’s brother Victor and his wife Lydia – and despite their packed schedule, the trip is smooth sailing until a hotel employee steps out of line. Meanwhile, Molly begins to reevaluate her inability to let things go.

Directors: Jay Ellis
Writer: Jason Lew
Lowkey Happy
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#10 - Lowkey Happy

Season 4 - Episode 8 - Aired 5/31/2020

Issa and Lawrence catch up and talk life, careers, past mistakes, and what makes each of them happy.

Directors: Ava Berkofsky
Lowkey Trying
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#11 - Lowkey Trying

Season 4 - Episode 9 - Aired 6/7/2020

Issa considers doing Nathan a platonic favor. Meanwhile, both Dr. Rhonda and Andrew ask Molly to consider a different approach in dealing with people who've wronged her, and Issa extends a timely olive branch.

Directors: Kerry Washington
Obsessed-Like
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#12 - Obsessed-Like

Season 3 - Episode 7 - Aired 9/23/2018

Issa tries to concentrate on her business plan but is driven to distraction; Molly steps out of her comfort zone in her love life.

Directors: Kevin Bray
Reunited, Okay?!
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#13 - 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
Growth, Okay?!
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#14 - 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
Pressure, Okay?!
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#15 - 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
Faulty, Okay?!
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#16 - 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
Surviving, Okay?!
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#17 - 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
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Tired, Okay?!
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#18 - 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
Chillin’, Okay?!
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#19 - 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
Choices, Okay?!
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#20 - 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
Out, Okay?!
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#21 - 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
Everything Gonna Be, Okay?!
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#22 - 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
Ready-Like
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#23 - Ready-Like

Season 3 - Episode 6 - Aired 9/16/2018

Issa needs moral support when her new project proves more complicated than she originally thought; Issa and Kelli press Molly to consider dating someone new; the girls attend Tiffany's baby shower and try to be helpful.

Directors: Liesl Tommy
Thirsty as F**k
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#24 - Thirsty as F**k

Season 1 - Episode 4 - Aired 10/30/2016

Although things are better than ever with Lawrence, Issa turns to Daniel for help during Career Day. Molly finds herself in a tough position when a partner asks her to give Rasheeda a talking-to. Facing disappointment at his new job, Lawrence bonds with a surprising confidante.

Directors: Kevin Bray
Shady as F**k
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#25 - Shady as F**k

Season 1 - Episode 5 - Aired 11/6/2016

Issa is mortified when a video of her profanity-laced rap at an open-mike night goes viral.

Directors: Melina Matsoukas
Writer: Ben Dougan