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.
Jerry Maguire used to be a typical sports agent: willing to do just about anything he could to get the biggest possible contracts for his clients, plus a nice commission for himself. Then, one day, he suddenly has second thoughts about what he's really doing. When he voices these doubts, he ends up losing his job and all of his clients, save Rod Tidwell, an egomaniacal football player.