Insecure - Episode Guide

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 gets advice from an unexpected source.

Issa and Lawrence try to move past their issues at home, as she deals with her colleagues' doubts and he gets a reality check from a head hunter. Molly introduces Jared to her friends, and later struggles to give words of wisdom to a new summer associate at work.

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.

A mortified Issa searches for a way to get her open mic video taken down and finds herself reconnecting with Daniel during a trip to his studio. Lawrence faces questions about his future with Issa. Molly invites her "perfect guy" Chris to her co-worker's engagement party, while attempting to navigate her "friendship" with Jared.

Issa tries to keep things together while hiding her guilt, as Lawrence doubles down on his commitment to her. Molly embraces a new relationship, but after learning more than she wants to about her new beau's past, struggles to focus on their 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.

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

Issa struggles in the aftermath of her breakup with Lawrence, while facing challenges at a new work assignment. Molly questions her worth at work. Lawrence adjusts to his new living arrangement.

Issa tries to make sense of a cryptic encounter. Lawrence considers crucial decisions. After being on the receiving end of 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 Dro, a childhood friend. A trip to the grocery store turns into a wild and crazy night for Lawrence.

Issa tries to build a roster at a work retreat, but butts heads with Frieda. Meanwhile, Molly's day takes an unexpected turn at her parents' vow renewal ceremony; and Lawrence stumbles upon news about Issa.

Issa maintains her roster but is met with disappointment as she finds herself without a car; Molly worries 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.

Issa, Molly and Lawrence face choices affecting their work and personal lives, and consider what the future holds for them.

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 Coachella 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 originally 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.

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

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.

The girls rally behind a friend. Molly and Andrew find themselves at a crossroads. Issa continues to search for happiness.

At her ten-year college reunion, Issa's self-doubt quickly surfaces, while Molly struggles to get out of her own head.

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 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.

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

A much-needed girls' night puts things into perspective for Issa and her crew.

Issa finds herself at a crossroads in both her career and relationship. Molly spends an emotional day getting her parents' will 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.

Looking back at five memorable seasons of Insecure, this documentary finds creator/star Issa Rae and others reflecting on the hit series.