John Cusack's Dating and Relationship History

Updated April 10, 2024 564.5K views 18 items

It's nearly impossible to avoid falling in love with John Cusack after seeing him in his iconic role as the lovesick Lloyd Dobler in Say Anything, as the bitter, yet romantic Rob Gordon in High Fidelity, or as any of the charming men he's played on the big screen. But what is his love life like in real life? Who has John Cusack dated? Now's your chance to learn about the famous women who've been lucky enough to have dated John Cusack. Fans will also enjoy these photos of young John Cusack and a votable list of John Cusack's best romantic roles.

If you're wondering who John Cusack's wife is, stop now - John Cusack has never married and does not have children! John Cusack's dating history is quite extensive, but since his 2011 relationship with Brooke Burns, his personal life has been kept private.

This list features John Cusack's ex-girlfriends along with additional information about them, such as when they were born and what they do professionally. These women may differ in personality and appearance, but what they all have in common is the fact that they've either dated or canoodled with John Cusack. It's easy to be jealous of the women John Cusack has gone out with, so you'll have to try to contain your envy.

The list you're viewing is made up of John Cusack's exes like Jennifer Love Hewitt and Uma Thurman. This list answers the questions, "What are the names of John Cusack's ex-girlfriends?," "Who has John Cusack been intimate with?" and "Who was John Cusack engaged to?"

Check out our list of women who dated John Cusack below.

Photo: Astrid Stawiarz / Getty Images
Brooke Burns
John Cusack and Brooke Burns first crossed paths in 2010, and the sparks ignited a brief but noteworthy romance. They were spotted at several high-profile events, sparking a flurry of romantic speculation in Hollywood's gossip mills. Despite the intense media scrutiny, Cusack and Burns managed to maintain their relationship out of the limelight. However, their romance was short-lived, and the couple called it quits in 2011. Despite the low-key nature of their relationship, they managed to leave an indelible mark on each other's lives.
More Brooke Burns
- #279 of 439 onThe 400+ Most Beautiful Women In Hollywood
- #23 of 138 onThe Best Hallmark Channel Actresses
- #84 of 312 onHallmark Channel Actors and Actresses
Photo: The Heart Truth / Wikimedia Commons
Rebecca Romijn
Cusack's shared screen space with Rebecca Romijn in 2004's The Punisher, and instant sparks flew between them. However, their relationship garnered widespread media attention only when they were publicly spotted together later that year. The handsome duo's chemistry was undeniable, making them one of Hollywood's exciting power couples. Unfortunately, their passionate romance came to an abrupt end in 2005. Their break-up was as quiet as their relationship, with both parties preferring to keep the details of their split private.
More Rebecca Romijn
- #67 of 1,285 onThe Most Beautiful Women Of All Time
- #171 of 439 onThe 400+ Most Beautiful Women In Hollywood
- #163 of 180 onThe Best Living American Actresses
Photo: Kevin Winter / Getty Images
Jennifer Love Hewitt
In 2003, John Cusack and Jennifer Love Hewitt began dating after they met while filming the movie Runaway Jury. Their on-screen chemistry was palpable, and it wasn't long before rumor mills started hinting at a budding romance. Cusack and Hewitt dated for a year, with their relationship generating a major buzz in Hollywood. However, the couple parted ways in 2004 for unspecified reasons. The duo maintained a dignified silence and kept the reasons for their split to themselves.
More Jennifer Love Hewitt
- Dig Deeper...What Really Happened To Jennifer Love Hewitt?
- #43 of 1,285 onThe Most Beautiful Women Of All Time
- #44 of 439 onThe 400+ Most Beautiful Women In Hollywood
Photo: Vince Bucci / Getty Images
Jodi Lyn O'Keefe
John Cusack started his relationship with actress Jodi Lyn O'Keefe in 2003. They met on the set of the thriller Identity where they played supporting roles. Despite the low-key nature of their relationship, they dated for almost six years until 2009. Their decision to part ways was mutual and amicable, making one of the longest relationships Cusack had been in.
More Jodi Lyn O'Keefe
- #457 of 1,134 onThe Most Beautiful Women In The World
- #533 of 1,102 onThe Most Beautiful Celebrities Of Our Time
- #114 of 138 onThe Best Hallmark Channel Actresses
Photo: Tinseltown / Shutterstock.com
Meg Ryan
Renowned for his long list of Hollywood relationships, John Cusack's pairing with Meg Ryan in 2002 was noteworthy. The fire was ignited when they met during the filming of the romantic film Serendipity. The couple's bond grew, and they dated for around a year. Though they made an adorable couple, the relationship didn't stand the test of time and ended in 2003. Nonetheless, their relationship made headlines and left fans speculating about what could have been.
More Meg Ryan
- Dig Deeper...Every Tom Hanks And Meg Ryan Movie, Ranked By Rom-Com Die-Hards
- And Deeper...Famous Scorpio Celebrities And Historical Figures
- #696 of 1,285 onThe Most Beautiful Women Of All Time
Photo: Telemundo / Wikimedia Commons / CC BY-SA 4.0
Gabriela Spanic
John Cusack was rumored to be dating Venezuelan actress Gabriela Spanic in 2003. The news of their budding romance captured the attention of both the Hollywood and Latin American media. However, their relationship was fleeting, and it fizzled out within a few months. Despite the brief duration of their affair, Spanic and Cusack remained close and maintained an amicable relationship after their split.
Photo: Arnaldo Magnani / Getty Images
Neve Campbell
John Cusack was linked to Canadian actress Neve Campbell in 1998 when they co-starred in the theatrical production of the film, The Raven. Their romantic connection was immediately noticeable on set, leading to a year-long relationship. Unfortunately, their blossoming love story concluded in 1999 due to their conflicting professional commitments.
More Neve Campbell
- Dig Deeper...Cool Facts About Neve Campbell That Made Us Scream For More
- And Deeper...Famous People Who Are Libra
- #353 of 1,285 onThe Most Beautiful Women Of All Time
Photo: Frank Trapper / Getty Images
Alison Eastwood
John Cusack's relationship with actress Alison Eastwood was reportedly sparked on the set of the film Midnight in the Garden of Good and Evil, where they first met in 1997. The pairing, however, was short-lived, reportedly ending in the same year it began due to personal differences and both actors' busy schedules.
Photo: Rune Hellestad / Getty Images
Minnie Driver
British actress Minnie Driver and John Cusack's love story began when they shared screen space in the 1997 film Grosse Pointe Blank. Their synergy was plausible on and off-set which led to a passionate romance. Unfortunately, their relationship lasted less than a year, ending soon after the film's release. Minnie Driver later revealed that she found out about their breakup from a celebrity interview with Cusack.
More Minnie Driver
- #136 of 200 onThe Best Actresses Working Today
- #123 of 166 onThe 100+ Most Stunning Women of the '90s
- #877 of 1,134 onThe Most Beautiful Women In The World
Photo: Ron Galella / Getty Images
Susannah Melvoin
In the early 1990s, John Cusack dated musician Susannah Melvoin, known for her association with Prince’s band, The Revolution. Their romance started organically through mutual friends, flourishing for some time despite their busy schedules. The reason for their split remains private, but their relationship reportedly ended on amicable terms.

Photo: Lev Radin / Shutterstock.com
Gina Gershon
Leading into the mid-1990s, John Cusack reportedly had a brief and undisclosed relationship with actress Gina Gershon. Their romance began on a low-key note; however, their break up also remained equally inconspicuous. They appeared to have ended things quietly, with the details of their dating history remaining largely unpublicized.
More Gina Gershon
- #305 of 348 onThe Best Actresses In Film History
- #178 of 200 onThe Best Actresses Working Today
- #963 of 1,285 onThe Most Beautiful Women Of All Time
Photo: Frank Trapper / Getty Images
Lili Taylor
One of Cusack's longest and most well-documented relationships was with actress Lili Taylor. The pair first met at an acting workshop in the 1980s and went on to date for a substantial period, building a strong bond both in their professional and personal lives. Sadly, their relationship ended in the late 80s for unspecified reasons but they remained friends, later co-starring together in various films.
More Lili Taylor
- #783 of 831 onThe Greatest Actors & Actresses In Entertainment History
- #1 of 82 onWho Is The Most Famous Taylor In The World?
- #5 of 16 on16 Female Character Actors You've Seen All Over But Can't Name
Photo: Walter McBride / Getty Images
Melissa Gilbert
In the 1980s, John Cusack dated actress Melissa Gilbert. Known for her role on Little House on the Prairie, Gilbert and Cusack began seeing each other early in their careers. Although they kept their relationship noticeably private, it is known that it lasted for about a year. The specifics of how they met and their relationship's end are somewhat of a mystery. Gilbert later became an acclaimed actress and best-selling author, while Cusack continued to enhance his acting career.
More Melissa Gilbert
- Dig Deeper...335+ Famous Taurus Historical Figures
- #170 of 227 onThe Most Trustworthy Celebrities In The World
- #141 of 298 onThe Best TV Actors And Actresses Of All Time
Photo: Frank Trapper / Getty Images
Claire Forlani
John Cusack had a relationship with British-American actress Claire Forlani in the early 1990s. They reportedly met on the set of a film, drinking in the atmosphere of Tinseltown. Their relationship attracted significant attention as both of them were on their way up the ladder of Hollywood stardom. Regrettably, their relationship came to an abrupt end after a couple of years. As to the reason for their split, nothing specific has ever been publicly stated.
More Claire Forlani
- #456 of 1,285 onThe Most Beautiful Women Of All Time
- #113 of 166 onThe 100+ Most Stunning Women of the '90s
- #161 of 1,134 onThe Most Beautiful Women In The World
Photo: Jiyang Chen / Wikimedia Commons / CC BY-SA 3.0
Uma Thurman
John Cusack allegedly dated the talented actress Uma Thurman in the mid-90s. The couple met while they were filming the romantic film Grosse Pointe Blank. Even though their romance was brief, lasting about a year, they reportedly had quite an intense relationship. Despite the end of their romance, they continued to remain friends and even worked together on several other films later.
More Uma Thurman
- Dig Deeper...Uma Thurman's Life Has Been Just As Crazy As The Bride's
- And Deeper...335+ Famous Taurus Historical Figures
- #57 of 200 onThe Best Actresses Working Today
Photo: Frederick M. Brown / Getty Images
Janice Dickinson
Janice Dickinson, known as the first supermodel, reportedly had a love affair with John Cusack, although the exact time is unclear. Their romance received massive attention because of Dickinson's prominence as a supermodel. Their relationship, however, was short-lived, and they ultimately decided to part ways.
More Janice Dickinson
- #32 of 80 onThe Best Reality Show Judges
- #90 of 213 on200+ Celebrities Who Went to Rehab
- #15 of 51 on51 Famous Survivors of Child Abuse
Photo: Lars Niki / Getty Images
Huma Abedin
John Cusack, in 2014, was rumored to be dating Huma Abedin, a political staffer and the former Deputy Chief of Staff to Hillary Clinton. Their supposed romance caused quite a stir in the press due to Abedin's political significance. However, their relationship never received public confirmation, making the timeline and details unclear.
Photo: Jeremiah Garcia / Wikimedia Commons / CC BY 2.0
Jami Gertz
The love story between John Cusack and Jami Gertz began in the 1980s. Both young actors at the time, they reportedly met at a film set. Their relationship got significant public attention due to their movie star status. However, they parted ways after a couple of years. Even though their relationship ended, they both had successful acting careers in Hollywood.
More Jami Gertz
- #217 of 1,285 onThe Most Beautiful Women Of All Time
- #645 of 1,102 onThe Most Beautiful Celebrities Of Our Time
- #44 of 99 onThe Greatest '80s Teen Stars