Movies like The Lonely Guy

About a Boy stars Hugh Grant as a perpetually single man who forms an unlikely friendship with a young boy, leading to his personal growth. The comedic journey and exploration of singleness and connection align well with themes found in The Lonely Guy.

In Her, Joaquin Phoenix portrays a lonely writer who develops an intimate relationship with an artificial intelligence operating system. This film offers a unique take on loneliness and the search for connection, offering a poignant perspective that viewers of The Lonely Guy might find resonant.

Bridget Jones's Diary is a romantic comedy chronicling the life of a single woman in London, played by Renée Zellweger, as she searches for love while navigating numerous mishaps. Its blend of humor and heart makes it a fitting companion for fans of The Lonely Guy.

High Fidelity, starring John Cusack, revolves around a record store owner and compulsive list maker who revisits his past relationships to figure out why he's so unlucky in love. It's a film for those who enjoy a blend of humor, introspection, and music within their romantic comedies, much like The Lonely Guy.

Annie Hall is another Woody Allen classic. It traces the rise and fall of a comedian's relationship with the eponymous character. With its witty dialogue, neurotic characters, and existential musings on love, Annie Hall caters to the same audience that appreciates the comedic yet tender storytelling of The Lonely Guy.

Play It Again, Sam features Woody Allen as a recently divorced film critic trying to navigate the murky waters of single life with the help of his idol, Humphrey Bogart. Like The Lonely Guy, it's a quirky, character-driven comedy that focuses on the trials and tribulations of romance and loneliness.