Insecure

On her 29th birthday, Issa gets fed up with her boyfriend and reunites with an ex at an open mic night, while Molly questions her single status.

Issa tries on a more audacious personality, but she's still avoiding Lawrence. Molly treats herself to a "fancy day" and meets up with a new man.

Lawrence and Issa try again. Molly learns more about Jared's background in the most awkward way possible. Issa hears her co-workers badmouthing her.

Molly's boss asks her to talk to a Black associate about the "company culture." Issa's class gets to know her a little too well on Career Day.

Issa needs that video to go away. She ropes in Daniel and Molly, who in turn calls up Jared... and they all end up somewhere they didn't expect.

Lawrence steps up his game, but Issa fights conflicting feelings. Molly gets uncomfortable when Jared shares something about his past.

Molly runs into an old friend who sings the praises of therapy. Issa's work fundraiser is on track to be a huge success — until Daniel shows up.

Lawrence says he's done with Issa but finds himself missing her. Issa tries to make up with Molly on a drama-filled girls trip with Kelli and Tiffany.