Follows the awkward experiences and racy tribulations of a modern-day African-American woman. Issa and Molly, these best friends must deal with their own real-life flaws as they attempt to navigate different worlds and cope with an endless series of uncomfortable everyday experiences.
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.
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.
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.