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 turns to Daniel for help during Career Day; Molly finds herself in a tough position at work; Lawrence bonds with a surprising confidante.
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 prepares for an important fundraiser; Lawrence considers a career opportunity; Molly encounters an old friend.
Issa tries to keep things together while hiding her guilt; Lawrence gets serious about his commitment to Issa; Molly embraces a new relationship.