Morgan Taylor has had a crush on her boss Omar Curry since they were in college. She's been working at his family's law firm for months, hoping to get close to him in every way possible. When Omar's dad suddenly suggest the two replace him and Omar's mother at a legal retreat in Jamaica, Morgan finally has her chance to be alone with the handsome attorney. But does he feel the same way? As the two descend on Ocho Rios, Jamaica, Morgan learns that sometimes going on vacation with the boss can be a good thing.