Two former co-workers, Eric and Alex, have been recently laid off of their jobs and they run into each other on a job interview. While searching for new jobs, they forge a personal relationship that involves Alex, a womanizing ladies' man, helping the naive and recently dumped Eric understand women better. Along the path are various dating scenarios from different characters that come in and out of the lives of both Alex and Eric who all demonstrate the struggles, strains, and triumphs of Dating While Black.