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 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.
Issa prepares for an important fundraiser at work, but faces an unexpected guest; Molly gets a new outlook on life.