Insecure as F**k
Written by Issa Rae & Larry Wilmore
Directed by Melina Matsoukas
Frustrated with her “token” status at work, and without plans on her 29th birthday, Issa unenthusiastically raps in the mirror to vent. She checks messages on her computer, careful not to wake her boyfriend, Lawrence. Discovering a "Happy Birthday. I miss you” message from her ex, Daniel, Issa wonders if she should be more like her successful best friend, Molly.
Molly chats with her coworker, Diane, excited about a guy she recently started dating. The conversation ends abruptly when she receives a text from him: “I’m not looking for a relationship right now,” followed by a sad face.
At dinner to celebrate Issa’s birthday, Molly confesses she’s confused about why this keeps happening to her. Issa makes her laugh by telling her it sounds like her “pu**y is broken.” Issa says she’s thinking about breaking up with Lawrence, but Molly calls her bluff.
Lawrence, depressed over a bad job interview, asks Issa if they can stay in for her birthday. Issa agrees, but covertly texts Daniel that she misses him, too.
At work the next day, Issa listens to her coworker Frieda discuss the kids from the day before. She imagines Frieda sharing statistics about black women remaining single and bursts out, “You’re wrong!” Caught in an awkward position, she covers by presenting a new idea: building a kids’ program outside of the school.
Molly heads into the office and finds a crowd surrounding the newly-engaged Diane. She smiles, but winds up calling Issa in tears. Having just seen a post for an open mic night Daniel will be attending, Issa tells Molly that she's taking her out.
Issa gets ready to go out for the night. Irritated when Lawrence comments that Molly’s “standards are way too high,” Issa hints at breaking up. She tells him she's spending the night at Molly's.
The club isn’t their scene, but Issa and Molly decide to make the most of it. A cute guy approaches Molly, and Issa is thrilled when Daniel finds her at the bar. Aware of Issa's rap ambitions, Daniel dares her to take the stage. Issa performs a rap titled “Broken Pu**y.” When Molly outs herself as the song's subject, the cute guy walks away.
In the car home, Molly is pissed Issa made a joke of her heartbreak, but Issa is distracted by a text from Daniel. Molly tells her she’d be stupid to sleep with him.
Issa shows up at Daniel’s. They begin to kiss, and she mentions jumping from relationship to relationship. He clarifies that’s not what he’s looking for. Issa shows up at Molly’s with chips and dip, and Molly lets in her best friend.