Insecure Season 1 Episodes

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Overview TV Listings Seasons & Episodes Cast

Season 1 Episode Guide

Episode 1 - Insecure As F**k

Series Premiere. In the wake of her 29th birthday, Issa Dee reconsiders her dead-end relationship with Lawrence, her live-in boyfriend. Meanwhile, Issa's best friend Molly mourns her singledom and the state of her 'lady parts.' Later, Issa uses an open-mic night as an excuse to reconnect with an ex.
Episode 1 - Season 1, Episode 1: Insecure As F**k

Series Premiere. In the wake of her 29th birthday, Issa Dee reconsiders her dead-end relationship with Lawrence, her live-in boyfriend. Meanwhile, Issa's best friend Molly mourns her singledom and the state of her 'lady parts.' Later, Issa uses an open-mic night as an excuse to reconnect with an ex.
Episode 2 - Messy As F**k

After the unexpected events of the previous night, Issa tries to decide what to do about Lawrence while sticking to her plan to embrace a bolder side of herself. Molly treats herself to a 'fancy day' and goes on a promising date. Lawrence searches for advice and finds it from an unexpected source.
Episode 2 - Season 1, Episode 2: Messy As F**k

After the unexpected events of the previous night, Issa tries to decide what to do about Lawrence while sticking to her plan to embrace a bolder side of herself. Molly treats herself to a 'fancy day' and goes on a promising date. Lawrence searches for advice and finds it from an unexpected source.
Episode 3 - Season 1, Episode 3: Racist As F**k

Issa and Lawrence try to move past their issues at home, as Issa deals with her colleagues' doubts and Lawrence gets a reality check from a head hunter. Molly introduces Jared to her friends and later struggles to give a new summer associate at work some words of wisdom.
Episode 3 - Racist As F**k

Issa and Lawrence try to move past their issues at home, as Issa deals with her colleagues' doubts and Lawrence gets a reality check from a head hunter. Molly introduces Jared to her friends, and later, struggles to give a new summer associate at work some words of wisdom.
Episode 4 - Season 1, Episode 4: Thirsty As F**k

Despite things being better than ever with Lawrence, Issa turns to Daniel for help during Career Day. Molly finds herself in a tough position when she's asked by a partner to give Rasheeda a talking to. Facing disappointment at his new job, Lawrence bonds with a surprising confidante.
Episode 4 - Thirsty As F**k

Despite things being better than ever with Lawrence, Issa turns to Daniel for help during Career Day. Molly finds herself in a tough position when she's asked by a partner to give Rasheeda a talking to. Facing disappointment at his new job, Lawrence bonds with a surprising confidante.
Episode 5 - Shady As F**k

A mortified Issa searches for a solution to a newfound problem. Lawrence faces questions about his future. Molly invites a 'perfect guy' to her co-worker's engagement party, while attempting to navigate her 'friendship' with Jared.
Episode 5 - Season 1, Episode 5: Shady As F**k

A mortified Issa searches for a solution to a newfound problem. Lawrence faces questions about his future. Molly invites a 'perfect guy' to her co-worker's engagement party while attempting to navigate her 'friendship' with Jared.
Episode 6 - Season 1, Episode 6: Guilty As F**k

Issa tries to keep things together as Lawrence doubles down on his commitment. Molly embraces a new relationship, but struggles to focus on the future.
Episode 6 - Guilty As F**k

Issa tries to keep things together, as Lawrence doubles down on his commitment. Molly embraces a new relationship, but struggles to focus on the future.
Episode 7 - Real As F**k

As Issa prepares for an important work fundraiser, her plan to keep focused gets derailed. Lawrence considers a career opportunity. Molly runs into an old friend with a new outlook.
Episode 7 - Season 1, Episode 7: Real As F**k

As Issa prepares for an important work fundraiser, her plan to keep focused gets derailed. Lawrence considers a career opportunity. Molly runs into an old friend with a new outlook.
Episode 8 - Season 1, Episode 8: Broken As F**k

Season One Finale. The lingering tension between Molly and Issa threatens to resurface during a girls' trip. Lawrence reconnects with his friends.
Episode 8 - Broken As F**k

Season One Finale. The lingering tension between Molly and Issa threatens to resurface during a girls' trip. Lawrence reconnects with his friends.
Episode 9 - Season 2, Episode 1: Hella Great

Season Two Premiere. Issa struggles in the aftermath of her breakup with Lawrence, while facing challenges at a new work assignment. Molly questions her worth at work, while Lawrence adjusts to his new living arrangement.
Episode 10 - Season 2, Episode 2: Hella Questions

Issa tries to make sense of a cryptic encounter. Lawrence considers some crucial decisions. After being on the receiving end of some harsh truths, Molly plots to join the office 'boys club.' Issa and Frieda encounter a problematic vice principal.
Episode 11 - Season 2, Episode 3: Hella Open

A sexually frustrated Issa explores a new dating outlook. On a girls' night out, Molly meets a promising new guy. Lawrence's commitment is tested by his new work friends.
Episode 12 - Season 2, Episode 4: Hella La

At a day party, Issa has her newfound confidence shaken. Molly has a blast from the past with childhood friend, Dro. A trip to the grocery store turns into a wild and crazy night for Lawrence.
Episode 13 - Season 2, Episode 5: Hella Shook

Issa attempts to build a roster and butts heads with Frieda at a work retreat. Molly's day takes an unexpected turn at her parents' vow renewal ceremony. Lawrence stumbles upon some news about Issa.
Episode 14 - Season 2, Episode 6: Hella Blows

Finding herself without a car, Issa is met with disappointment as she maintains her roster. Molly frets about an important friendship while embracing something new. Lawrence gets a rude awakening at work after pitching his app.
Episode 15 - Season 2, Episode 7: Hella Disrespectful

Tensions run high during Derek and Tiffany's dinner party. Molly rethinks her future after being forced to come to terms with her romantic realities. Issa tries to make things right with Frieda.
Episode 16 - Season 2, Episode 8: Hella Perspective

Season Two Finale. Over the course of one pivotal month, Issa, Molly and Lawrence face choices impacting their work and personal lives, with each considering whether to embrace a new future or look back to the past.
Episode 17 - Season 3, Episode 1: Better-Like

Season Three Premiere. Issa crashes on Daniel's couch and tries to save up some extra cash. Molly returns from a beach vacation with renewed determination to maintain boundaries in her life.
Episode 18 - Season 3, Episode 2: Familiar-Like

Issa gets advice from Kelli about her financial situation. Later, Issa plays wing woman as Daniel tries to make a music-industry connection.
Episode 19 - Season 3, Episode 3: Backwards-Like

Issa is inspired while recruiting at a job fair with Frieda. Later, Issa treats Daniel to a thank-you dinner as she remains hopeful about their future. Molly starts her dream job at a black-owned law firm.
Episode 20 - Season 3, Episode 4: Fresh-Like

Issa tries to let go of some cherished mementos. At work, Frieda tries to help Issa get back in Joanne's good graces. Molly bonds with her new colleagues about an over-confident associate and vents to her therapist about her status at work.
Episode 21 - Season 3, Episode 5: High-Like

The girls take a trip to a music festival to celebrate Tiffany. Molly has trouble leaving her obsession with work behind.
Episode 22 - Season 3, Episode 6: Ready-Like

Issa needs moral support when her new project proves more complicated than she thought. Issa and Kelli press Molly to consider dating someone new. Later, the girls attend Tiffany's baby shower and try to be helpful.
Episode 23 - Season 3, Episode 7: Obsessed-Like

Issa tries to concentrate on her business plan but is driven to distraction. Molly steps out of her comfort zone in her love life.
Episode 24 - Season 3, Episode 8: Ghost-Like

Season Three Finale. After facing numerous obstacles, Issa gets discouraged about her project. Molly helps give Issa a drama-free 30th birthday.
Episode 25 - Season 4, Episode 1: Lowkey Feelin' Myself

Season 4 Premiere. 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.
Episode 26 - Season 4, Episode 2: Lowkey Distant

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.
Episode 27 - Season 4, Episode 3: Lowkey Thankful

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.
Episode 28 - Season 4, Episode 4: Lowkey Losin' It

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.
Episode 29 - Season 4, Episode 5: Lowkey Movin' On

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.
Episode 30 - Season 4, Episode 6: Lowkey Done

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.
Episode 31 - Season 4, Episode 7: Lowkey Trippin'

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.
Episode 32 - Season 4, Episode 8: Lowkey Happy

Issa and Lawrence catch up and talk life, careers, past mistakes, and what makes each of them happy.
Episode 33 - Season 4, Episode 9: Lowkey Trying

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.
Episode 34 - Season 4, Episode 10: Lowkey Lost

Season Four Finale. 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.
Episode 35 - Season 5, Episode 1: Reunited, Okay?!

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.
Episode 36 - Season 5, Episode 2: Growth, Okay?!

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.
Episode 37 - Season 5, Episode 3: Pressure, Okay?!

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.
Episode 38 - Season 5, Episode 4: Faulty, Okay?!

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.
Episode 39 - Season 5, Episode 5: Surviving, Okay?!

A family emergency finds Molly stretched thin. Issa and her new man grow closer than ever.
Episode 40 - Season 5, Episode 6: Tired, Okay?!

A distracted Issa mulls over difficult choices in both work and love, while Molly finds a comforting audience in an unlikely source.
Episode 41 - Season 5, Episode 7: Chillin', Okay?!

A long overdue girls’ night filled with self-reflection and real talk puts things into perspective for Issa and her friends.
Episode 42 - Season 5, Episode 8: Choices, Okay?!

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.
Episode 43 - Season 5, Episode 9: Out, Okay?!

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.
Episode 44 - Season 5, Episode 10: Everything Gonna Be, Okay?!

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.
Episode 45 - Season 5, Episode 11: The End

In 2016, Insecure burst onto the television scene with a dynamic, hilarious, and vulnerable point-of-view like none other. Looking back at five memorable seasons of messy relationships and hella personal growth, INSECURE: THE END finds cast members, producers, writers, directors, crew, and, of course, the incomparable creator/star Issa Rae, reflecting on the series' genesis and the legacy it leaves behind. A love letter to those who brought the show to life and the fans who embraced it with open arms, this behind-the-scenes documentary highlights Insecure's commitment to authenticity, representation, and diversity - in front of and behind the camera - and is an intimate and celebratory farewell to one of HBO's most iconic comedies.


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