Prisoner of Love follows Chelsea Holmes, the self-proclaimed "prison matchmaker," as she dedicates her time to helping men and women living free lives find love with prisoners behind bars. And Chelsea isn't simply a matchmaker, she is also looking for love with someone on the inside. Prisoner of Love documents couples as they navigate the unique struggle of dating someone in prison. Chelsea does all she can to give these singles the tools to make their relationships successful beyond prison walls, but are these matches built to last?