After her 29th birthday, Issa reconsiders her relationship with live-in boyfriend Lawrence, and reconnects with an ex at an open-mic night; 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.

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 her friends to Jared.

Issa asks Daniel for help during Career Day; Molly finds herself in a tough position at work; Lawrence bonds with a surprising confidante.

Issa desperately tries to find a way to take down her open mic video that has surfaced online; Molly invites her perfect guy to a party.

As Lawrence gets serious about his commitment to Issa, she attempts to keep things together; Molly struggles with a new boyfriend's past.