I Want Someone to Eat Cheese With 2007

James, a struggling improv actor affiliated with Second City, faces the uphill battle of managing his weight, battling depression, and feeling stuck in life in the vibrant city of Chicago. Despite his attempts to sneak in indulgences on his diet, the weight of his insecurities drags him down further. After an embarrassing stunt on his TV prank show, which leads to its abrupt end, he finds himself in a state of disarray.

The fallout is immediate and painful: his girlfriend Andrea cuts ties, and his agent, Herb, no longer represents him. The final straw occurs when he makes a fool of himself during Career Day at an elementary school, where he shares his personal struggles, much to his dismay, in front of the teacher, Stella.

Seeking solace, James often parks his car outside Wrigley Field as the sun sets, enjoying the picturesque views and reflecting on his life. By day, he wanders Chicago’s North Side alongside his friend Luca, who encourages him with the beauty of their surroundings.

Everything shifts one day when James, dressed as a pirate for a hot dog stand, serendipitously learns about a local remake of his favorite film, Marty (1955). Although he knows the director, his attempt to secure an audition falls flat. Defeated, he leaves a Compulsive Eaters Anonymous meeting and finds himself indulging in ice cream to find comfort.

It is here that Beth enters his life—an alluring woman who recognizes him from Second City and offers him complimentary ice cream. While conversing, Beth poses a quirky question, explaining it thoughtfully, which captivates James. As romance blossoms, Beth invites him on adventures, including a shopping spree where she tries on underwear.

Their relationship flourishes with Beth attending one of James’ comedy shows and daring to visit his apartment, shared with his mother. As the chemistry builds, she offers to return to his place, indicating their relationship is deepening.

However, as events unfold, it becomes clear Beth has reservations—she admits she has never been with someone of James’ stature before, leading to heartbreak when she turns him away the next day, feeling unprepared for the relationship’s demands. The situation worsens when James discovers that the role he coveted in Marty has been snatched by teen heartthrob Aaron Carter.

As the narrative progresses, James starts to embark on a new journey in his life. He moves into his own apartment, rekindles a connection with Stella, and continues to chase his acting dreams, demonstrating resilience in the face of adversity.