Jamie is moving in two weeks from Chicago to New York hoping to become a Broadway actress. Her best friend Jessica is bummed because she's not-so-secretly in love with Jamie. As moving day gets closer, Jessica tries to make Jamie jealous by dating other girls. But Jessica's plan backfires, in a way she could never imagine. Set in working class Chicago and infused with musical dance numbers, "Jamie and Jessie are Not Together" is a love letter to those gray areas of love and lust and to the young romances we will never forget.

Two recent exes with an undeniable connection confront what could have been if their cultural differences hadn't pushed them to new lives on opposite coasts.