40 is the New 20(2009)

movie - first aired/released 2009-05-29 - audience 5.0

When he learns that a co-worker is friends with his old high-school girlfriend, Jennifer, stockbroker Gary helps his former flame get a job at his company in order to pursue her affections all over again. But when Jennifer rejects his advances and dates other men, Gary becomes increasingly obsessed with winning her back.