John Cusack, Age 53 – Single

There have been many women that have had the chance of dating John Cusack and as it just so happens, most of them were famous. To be fair, after playing in so many iconic movies in the 80s and 90s who wouldn’t want to date John. However, he’s never actually met the person to make him decide to get married.

Some of his famous relationships include a short-lived one with Minnie Driver sometime around 1996. Two years later he started dating Neve Campbell whom she met in Canada while she was filming for a movie and they split up in 2002.  John played in Never Grow Old n 2019.