“Say Anything” Star John Cusack’s Complete Dating History

Hollywood icon John Cusack has played numerous charming roles on the big screen, making it easy for fans to fall in love with him. Despite his status as a beloved actor, John Cusack’s dating history is as fascinating as his filmography. Now 58, Cusack remains unmarried and childless, but his romantic past is quite extensive.

Alison Eastwood – 1997

John Cusack dating Alison Eastwood in 1997 was a hot topic in Hollywood. Alison, the daughter of legendary actor Clint Eastwood, was an up-and-coming actress at the time. Their romance was brief but highly publicized, capturing the interest of fans and tabloids alike.

The couple’s relationship was filled with the typical Hollywood glamour and mystery. However, like many celebrity romances, it eventually fizzled out. Despite their short-lived romance, Cusack and Eastwood’s time together remains a memorable chapter in his dating history.

Marca / John Cusack, now 58, is not married and has no kids. But his dating history is quite extensive.

Neve Campbell – 1998

In 1998, John Cusack dating Neve Campbell made headlines. Neve, known for her roles in “Party of Five” and “Scream,” was at the peak of her career. Their relationship seemed like a perfect match between two rising stars in Hollywood.

The duo was often spotted together, enjoying each other’s company at various events. Despite the chemistry and public interest, their relationship was short-lived. Still, Cusack and Campbell’s romance remains a notable part of his dating history.

Meg Ryan – 2002

John Cusack dating Meg Ryan in 2002 was a surprise to many. Meg, America’s sweetheart known for her roles in romantic comedies, was a major star. Their relationship attracted significant media attention, given their status as prominent Hollywood figures.

Jennifer Love Hewitt – 2003

In 2003, John Cusack dating Jennifer Love Hewitt became a popular topic. Jennifer, a star in her own right, was famous for her roles in “Party of Five” and “I Know What You Did Last Summer.” Their relationship was another example of Cusack’s attraction to talented actresses.

Although their romance did not last, it remains a noteworthy part of Cusack’s dating history.

Ranker / Despite the brevity, Cusack and Meg Ryan’s time together added an interesting twist to his romantic history.

Jodi Lyn O’Keefe (2003 – 2009)

One of the longest relationships in John Cusack’s dating history was with Jodi Lyn O’Keefe. Jodi, known for her role in “Nash Bridges,” started dating Cusack in 2003. Their relationship lasted until 2009, marking one of Cusack’s most significant romantic commitments.

During their time together, the couple was often seen enjoying private moments and attending events. Despite their long-term relationship, they eventually went their separate ways. Their breakup marked the end of an era in Cusack’s romantic life.

Rebecca Romijn – 2004

John Cusack dating Rebecca Romijnin in 2004 added another interesting chapter to his romantic history. Rebecca, known for her role as Mystique in the “X-Men” series, was a stunning addition to Cusack’s list of girlfriends.

Ranker / Although John Cusack’s relationship with Rebecca Romijn was brief, it was widely talked about.

The couple’s time together was characterized by glamorous outings and red-carpet appearances. However, their romance was short-lived, and they eventually parted ways. Despite this, Cusack and Romijn’s relationship remains a memorable part of his dating timeline.

Brooke Burns – 2010

In 2010, John Cusack dating Brooke Burns captured the media’s attention. Brooke, a former “Baywatch” star, was known for her beauty and charm. Their relationship was another high-profile addition to Cusack’s romantic history.

However, despite the brief romance, Cusack and Burns’ time together is a notable part of his dating history.