At her 10-year college reunion, Issa's self-doubt quickly surfaces, while Molly struggles to get out of her own head.
Molly contemplates jumping back into the dating pool; Issa leans on an old friend.
Molly and Issa assess their relationships to figure out who and what still matters.
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.
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 is at a crossroads with both her career and relationship; Molly spends an emotional day putting her parents' wills in order.
A farewell party nudges Issa to face her unresolved feelings; having spent all day enjoying herself, Molly finally confronts her fears.
With Condola's guidance, Issa prepares for a mixer in her courtyard to pitch the block party to potential sponsors, but tensions arise 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 date night.
While Molly's family celebrates Thanksgiving together, Issa and Ahmal decide to do their own thing; when Lawrence joins Friendsgiving at Condola's house, the new couple breaks some awkward ground.
The women get together to help Tiffany with her new baby girl; 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; Tiffany enjoys a break from her baby, Kelli entertains a gullible new boo, and Molly attempts to put a grudge on hold.
Molly and Andrew take off for their first couples' vacation with Andrew's brother, Victor, and his wife, Lydia, and the trip is smooth sailing until a hotel employee steps out of line; Molly reevaluates her inability to let things go.
Issa and Lawrence catch up and talk about life, careers, past mistakes, and what makes each of them happy.
Issa considers doing Nathan a favor; Dr. Rhonda and Andrew ask Molly to consider a different approach in dealing with people who have wronged her.
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.
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; 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.
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; Molly helps give Issa a drama-free 30th birthday.
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 receiving 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 outlook on dating; on a girls' night out, Molly meets a promising new guy; Lawrence's new work friends test his commitment.
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 news about Issa.
Issa finds 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 reconsiders her future after facing her romantic reality; 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.
After her 29th birthday, Issa Dee reconsiders her relationship with her live-in boyfriend, Lawrence; Issa's best friend, Molly, laments being single; Issa reconnects with an ex at an open-mic night.
Issa attempts to make a decision 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 some advice.
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 head hunter; Molly introduces Jared to her friends.
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 coworker's 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.
Issa prepares for an important fundraiser; Lawrence considers a career opportunity; Molly encounters an old friend.
Tension between Molly and Issa threatens to resurface during a trip; Lawrence reconnects with his friends.