After her 29th birthday, Issa Dee reconsiders her relationship with her live-in boyfriend, Lawrence, and reconnects with an ex at an open-mic night. Meanwhile, Issa's best friend, Molly, laments being single.
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, and Lawrence gets some advice.
While working through their issues at home, Lawrence gets a reality check from a headhunter, and Issa deals with doubts about her at work. Meanwhile, Molly decides to introduce Jared to her friends.
Issa turns to Daniel when she needs some help for Career Day, Molly finds herself in a tough situation at work, and Lawrence bonds with a surprising confidante.
Issa desperately searches for a way to get her open mic video taken down and reconnects with Daniel. Meanwhile, Lawrence faces questions about his future with Issa, and Molly invites her ideal guy to a coworker's engagement party.
As Lawrence gets serious about his commitment to Issa, she tries to keep things together while hiding her guilt, and Molly struggles with her new boyfriend's past.
Issa Rae
Issa
Yvonne Orji
Molly
Jay Ellis
Lawrence
Lisa Joyce
Frieda
Natasha Rothwell
Kelli