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.
Issa is mortified when a video of her profanity-laced rap at an open-mike night goes viral.
Issa tries to hide her guilt from Lawrence, who reiterates his love for her. Meanwhile, Molly dives into a new romance, but has second thoughts about the future after learning unsavory details about her new boyfriend's past.
Issa preps for a fund-raiser, but has trouble staying focused. Meanwhile, Lawrence mulls a job opportunity; and Molly learns something new from an old friend.
Molly and Issa's trip could be undone by lingering tension between them; and Lawrence catches up 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, 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.
Issa's sexual frustration prompts her to reassess her dating outlook; Molly meets a potential beau on a girls' night out; Lawrence's new work friends test his commitment.
Issa's newfound confidence is shaken at a day party; Molly has an eventful reunion with a childhood friend; Lawrence's trip to the grocery store turns into a wild and crazy night.
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.
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.
Over the course of one pivotal month, Issa, Molly and Lawrence face choices affecting their work and personal lives, with each considering whether to embrace a new future or look back to the past.
Issa crashes on Daniel’s couch and tries to save up 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 and plays wingwoman as Daniel tries to make a music-industry connection.
Issa is inspired while recruiting at a job fair with Frieda. Later, she 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 weekend trip 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; 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, while 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.
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 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 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.
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.
Creator and star Issa Rae and showrunner Prentice Penny break down the first episode and how they’re setting the tone for the rest of the season.
Creator and star Issa Rae and showrunner Prentice Penny sit down with Yvonne Orji to unpack Molly’s relationship with Andrew and Issa’s friendship with Condola.
Creator and star Issa Rae and showrunner Prentice Penny are joined by Christina Elmore to discuss Condola and Lawrence’s interesting first Thanksgiving together and debate whether or not it’s possible to be friends with an ex.
Creator and star Issa Rae and showrunner Prentice Penny sit with Natasha Rothwell to discuss the shifting dynamics within the friend group.
Issa Rae, Prentice Penny and Jean Elie discuss Issa and Molly’s blowout fight as well as the dynamic between Ahmal and Kelli.
Issa Rae and Prentice Penny unpack Issa’s mindset after her fight with Molly at the block party.
Issa Rae and Prentice Penny are joined by Alexander Hodge to talk about what Molly and Andrew learn about themselves and their relationship during their first vacation together.
Issa Rae, Prentice Penny and Jay Ellis dive deep into the unfinished business Lawrence and Issa have with each other.
Issa Rae and Prentice Penny are joined by Kendrick Sampson to discuss Nsthan's lingering feelings for Issa and destigmatizing mental illness.
Issa Rae and Prentice Penny sit down with Amanda Seales to unpack the finale.
Looking back at five memorable seasons of Insecure's messy relationships and hella personal growth, this documentary finds creator/star Issa Rae and others reflecting on the hit series.
