Mike Sullivan works as a hit man for crime boss John Rooney. Sullivan views Rooney as a father figure, however after his son is witness to a killing, Mike Sullivan finds himself on the run in attempt to save the life of his son and at the same time looking for revenge on those who wronged him.
When record store owner Rob Gordon gets dumped by his girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in an attempt to figure out what went wrong. As Rob seeks out his former lovers to find out why they left, he keeps up his efforts to win Laura back.