5. John Cusack
Age: 59 (28 June 1966)
Known for his roles in Say Anything and High Fidelity, John Cusack has never tied the knot. The actor has been open about his reasons for remaining unmarried, stating that he’s never felt the need to make that commitment. Cusack’s philosophy is one of independence and individuality, preferring to focus on his creative endeavors rather than societal norms.