Insecure, Seasons 1-5

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.

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.

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.

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.

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.

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.

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.

Season One Finale. The lingering tension between Molly and Issa threatens to resurface during a girls' trip. Lawrence reconnects with his friends.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Issa gets advice from Kelli about her financial situation. Later, Issa plays wing woman as Daniel tries to make a music-industry connection.

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.

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.

The girls take a trip to a music festival to celebrate Tiffany. Molly has trouble leaving her obsession with work behind.

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.

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

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

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.

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.

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.

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.

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.

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.

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.

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

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.

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.

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.

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.

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.

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.

A family emergency finds Molly stretched thin. Issa and her new man grow closer than ever.

A distracted Issa mulls over difficult choices in both work and love, while Molly finds a comforting audience in an unlikely source.

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

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.

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.

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.

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.

A comical peek at Issa Rae in this comedy series that looks at the friendship of two modern-day black women and all of their tribulations.

Visit the Los Angeles set and locations for a day of shooting the comedy series 'Insecure' with creator and star Issa Rae.

A conversation with Issa Rae and others from her hilarious new comedy series 'Insecure.'

Get an extended look at the 'Insecure' characters' favorite reality show, 'Conjugal Visits.'

Ready for more Issa? See what's coming for her in Season 2 of the hit HBO comedy series 'Insecure.'

Creator and star Issa Rae and executive producers Prentice Penny and Melina Matsoukas talk Season 2 of 'Insecure.'

Get an inside look at Sn 2 / Ep 1 of the HBO series 'Insecure.'

Get an inside look at Sn 2 / Ep 2 of the series 'Insecure.'

Get an inside look at Sn 2 / Ep 3 of the series 'Insecure.'

Get an inside look at Sn 2 / Ep 4 of the series 'Insecure.'

Get an inside look at Sn 2 / Ep 5 of the series 'Insecure.'

Get an inside look at Sn 2 / Ep 6 of the series 'Insecure.'

Get an inside look at Sn 2 / Ep 7 of the series 'Insecure.'

Get an inside look at Sn 2 / Ep 8 of the series 'Insecure.'

See every scintillating episode of 'Due North' the fictional and very funny soap parody seen in Season 2 of 'Insecure.'

Check out what's coming in Season 3 of the hit comedy series 'Insecure' starring Issa Rae.

It's the first day on the Season 3 set of 'Insecure.' Hear what Issa Rae and her fellow cast and crew have to say before the cameras roll.

Get an inside look at Sn 3 / Ep 1 of the HBO series 'Insecure.'

Get an inside look at Sn 3 / Ep 2 of the HBO series 'Insecure.'

Get an inside look at Sn 3 / Ep 3 of the HBO series 'Insecure.'

Get an inside look at Sn 3 / Ep 4 of the HBO series 'Insecure.'

Get an inside look at Sn 3 / Ep 5 of the HBO series 'Insecure.'

Get an inside look at Sn 3 / Ep 6 of the HBO series 'Insecure.'

Get an inside look at Sn 3 / Ep 7 of the HBO series 'Insecure.'

Get an inside look at Sn 3 / Ep 8 of the HBO series 'Insecure.'

Join Yvonne Orji on the set of "Insecure" as she talks about playing "Molly" in Season 3.

From hair and makeup to shooting a baby shower scene, follow Amanda Seales as she transforms into "Tiffany" for Season 3 of "Insecure."

Visit with Natasha Rothwell on the Season 3 set of "Insecure" as she opens up about her character "Kelli."

Delve inside Season 3 of 'Insecure' with director Millicent Shelton.

Delve inside Season 3 of 'Insecure' with director Stella Meghie.

Delve inside Season 3 of 'Insecure' with director Prentice Penny.

The cast of Insecure provides insight about the growth of their characters.

An all new trailer for Insecure, Season 5.

A look back to Season Inesure Seasons 1-4.

Cast and crew discuss the final season.

Show creator Issa Rae, executive producer Prentice Penny and costume designer Shiona Turini discuss epsidoe 2 of the final season.

Show creator Issa Rae, executive producer Prentice Penny and episode director Melina Matsoukas discuss epsidoe 1 of the final season.

Show creator Issa Rae, executive producer Prentice Penny and episode actress Christina Elmore discuss epsidoe 3 of the final season.