Insecure

In the wake of her 29th birthday, Issa reflects on her life and relationship choices.

Issa struggles with her feelings about Lawrence, work, and her life.

Issa and Lawrence try to move past their issues at home; Issa deals with doubts from her colleagues; Lawrence gets a reality check from a headhunter; Molly introduces Jared to her friends.

Issa turns to Daniel for help during Career Day; Molly finds herself in a tough position at work; Lawrence bonds with a surprising confidante.

Issa searches for a way to get her open mic video taken down; Issa reconnects with Daniel; Lawrence faces questions about his future with Issa; Molly invites her "perfect guy" to a coworkers engagement party.

Issa tries to keep things together while hiding her guilt; Lawrence gets serious about his commitment to Issa; Molly embraces a new relationship.

[HBO] HD. 'Real as F**k.' (Season One) Issa deals with drama at a work fundraiser; later, she clashes with Molly over life choices.

A girls' trip finds Issa and Molly in close quarters, while Lawrence vents with his boys.

Issa struggles after the break with Lawrence and difficulties with a new task at work. Molly doubts her worth at work, and Lawrence adapts to his new housing situation.

Issa tries to make sense of a cryptic encounter; Lawrence considers crucial decisions; after receiving some harsh truths, Molly plots to join the office "boys club"; Issa and Freida encounter a problematic vice principal.

A sexually frustrated Issa explores a new outlook on dating; on a girl's night out, Molly meets a promising new guy; Lawrence's new work friends test his commitment.

Issa's confidence is shaken; Molly hangs with a childhood friend; Lawrence has a wild and crazy night.

Issa explores casual relationships; Molly learns some new truths; Lawrence stumbles on news.

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.

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 impacting 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 cherished mementos; Molly vents to her therapist about 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. 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.

While Issa and Condola continue planning for the Block Party, both are made aware that Condola is seeing Lawrence. Meanwhile, Molly may be developing feelings for Andrew, who wants to keep his options open.

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 date night.

Issa and Molly prepare to spend Thanksgiving with their families while Lawrence makes his way to Condola's "Friendsgiving." But as the night progresses, truths surface for each party that no one was expecting.

When Issa has a block party crisis, she turns to a reluctant Molly for help.

Issa works around the clock to ensure the event goes off without a hitch.

Feeling deflated after the block party, Issa seeks comfort.

Molly and Andrew embark on the ultimate double-date.

Each reflecting on past mistakes and lessons learned, Issa and Lawrence discuss happiness.

Issa extends a timely olive branch to a friend.

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.

Eager to embrace newfound responsibilities, one of Issa's exes finds himself torn between two places.

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, 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.