40 is the New 20

In 40 is the New 20, stockbroker Gary learns that a co-worker is friends with his former high-school girlfriend, Jennifer. Eager to win her back, he helps Jennifer secure a job at his company. However, when she starts dating other men, Gary's obsession grows, complicating his pursuit of her affections.

This film features a cast including Pat Mastroianni, Claudia Ferri, Bruce Dinsmore, and Charles Bender. As a comedy from 2009, it reflects the humor and relationship dynamics of its era, making it a fitting choice for collectors interested in contemporary comedies. The film's premise offers a mix of romantic pursuits and comedic missteps, characteristic of the genre.