John Cusack's Relationship History Is Packed With A-Listers: The Gorgeous Women He's Dated

If there is one thing that has remained constant throughout John Cusack's 40-plus-year career as a Hollywood star, it's his insistence on privacy. So fiercely has he been about keeping even the barest details of his personal life under wraps — especially those regarding his relationships with women — that, to date, it is hard to ascertain who he has truly been romantically involved with.

Whether they like it or not, celebrities' private affairs have become an inevitably huge part of the deal that keeps them relevant to the public. However, Cusack's stance on protecting his privacy has been as unapologetic as his views on marriage, which he famously summarized in a seven-word statement to Elle: "Society doesn't tell me what to do." 

So though his relationship history is packed with A-listers, Cusack has rarely offered any comment on it or on any of the people involved, leaving fans to piece the story together on their own. Here's a list of the women John Cusack has dated (or is rumored to have dated). 

Early in his career, when he was just beginning to find his footing in Hollywood, John Cusack landed smack in the middle of a love triangle involving one of his closest industry friends and his girlfriend. The couple in question were Rob Lowe and Melissa Gilbert, who shared a famously turbulent on-again, off-again relationship between 1981 and 1987. Much like it did for his friend and "Class" co-star Cusack, that period in the '80s proved professionally conducive for Lowe. And as female attention toward Lowe increased in the wake of his growing success, so did the issues in his personal life with Gilbert.

Lowe was unfaithful to Gilbert during their relationship — a fact he has openly admitted to — and this inevitably affected Gilbert, who decided to give her then-boyfriend a taste of his own medicine. And that is when Cusack got pulled into the messy affair. As Gilbert recounted in her memoir "Prairie Tale," she was on a shoot in Chicago, where Cusack was stationed at the time. Lowe had apparently called his friend and asked him to show Gilbert around the city. "He did, and we ended up having a little fling, which I kept from Rob," Gilbert wrote. "It was my own private 'screw you.' Only John and I ever knew about it." 

Another name John Cusack was linked to early in his career was Susannah Melvoin — the vocalist best known in pop culture for her association with music legend Prince. She earned the latter distinction in the mid-1980s, when she came into Prince's ambit through her musician sister and eventually joined his lineup, and, sometime later, apparently started going out with Cusack. 

While the exact timeline of their affair is unclear, it is believed that Melvoin and Cusack were an item when the star was working on his 1989 teen classic "Say Anything." As his co-star Ione Skye recounted in her memoir "Say Everything," Cusack had hinted at his relationship with Melvoin being more than just a fling (via Entertainment Weekly). "I've never been in love. At least not till recently," Cusack apparently told Skye, who went on to admit that she initially mistook his remark as a disclosure of his affection for her. (That love story would take its own course later in Cusack's life.) 

The seriousness of their relationship notwithstanding, Cusack and Melvoin seemed to be inseparable for a hot moment between the late '80s and early '90s. The singer was by Cusack's side for several Hollywood events, including "The Grifters" premiere and the 1991 Golden Globes. And while the pair was not photographed together for a brief period in the mid-'90s, they were spotted hand in hand again at the premiere of Cusack's film "City Hall" in 1996.

Let's rewind to the 1980s for a second. John Cusack was shooting "Say Anything" (check out things you only notice as an adult) — which, by many accounts, is considered his big Hollywood breakthrough as a rom-com hero — when he crossed paths with Ione Skye. The two were convincing on screen as endearing underdog Lloyd Dobler and smart A-grader Diane Court, a high school couple fighting against all odds to be together. But even after the cameras stopped rolling, some sparks apparently continued flying between Cusack and Skye. 

As Skye recalled in her 2025 memoir, her teenage crush on Cusack reared its head passionately when the two were on set having conversations about love, which left Skye with a tangle of questions: "As our romance had grown on camera, a real attraction had grown as well. I felt it all the time and knew he did too, but we'd just let it be on film," she wrote via Entertainment Weekly. 

Their youthful attraction culminated years later in a brief fling after Skye's divorce from musician Adam Horovitz in 2000. "I'd needed to get him out of my system and it had worked — now I knew we were meant to be in love only in the movies," she shared matter-of-factly. Skye told People that she had given Cusack a copy of her book before publication and that he had reverted with some feedback: "You made the experience sound so meh! It wasn't 'meh' for me."

John Cusack and Uma Thurman are two names that don't seem to fit into one pairing. Though both have been Hollywood icons for decades, their respective filmographies have never overlapped. Nor have they ever been memorably photographed together in public. To the uninitiated, Cusack and Thurman would appear to simply be two celebrities with unrelated lives. However, those who were conscious witnesses to '90s Hollywood know otherwise. 

Cusack and Thurman were one of the industry's most well-known couples sometime in the '90s — a decade of growing stardom for both of them. Through the '80s, Cusack had firmly established his place in cinema as a youth heartthrob, while Thurman, who was yet to hit career greatness with "Pulp Fiction," had also begun making her way up the ladder with films like "Dangerous Liaisons." The coming together of these two young talents naturally grabbed attention. 

It is believed they first got together after Thurman's divorce from Gary Oldman in 1992. And though they eventually broke up and Thurman moved on and married Ethan Hawke in 1998, it didn't signal the end of their story. After Thurman's heavily publicized split from Hawke in 2003, Cusack again became the shoulder his ex-girlfriend leaned on for support. Interestingly, his love affair with Thurman is among the few romantic encounters from his life Cusack has openly admitted to, telling talk show host Howard Stern: "I dated Uma. Yeah. For a second."

Though he has denied ever being in a relationship with Minnie Driver, John Cusack was linked to her in the past. The timeline of their brief romantic affair apparently coincided with the 1997 film "Grosse Pointe Blank," the only film in which they have co-starred. Cusack led the acclaimed dark comedy as an assassin who reconnects with his former flame (played by Driver) upon returning to his hometown. 

Cusack was also a writer and producer for the film and, according to Driver, helped in great measure to turn the script into the success it finally became. As she recalled on James Corden's "This Life of Mine," Cusack got everyone aboard a "... moving creative train" and gunned for greater improvisation. "I got sort of vaulted into this because I read with Cusack and we had this massive connection," she said (via Entertainment Weekly).  

Chuffed as she sounded about having shared a moment with Cusack in the '90s, Driver didn't confirm an off-screen romance with him. "I knew that this was in a bubble, and I probably wasn't going to make a film like this again." Considering that she famously dated her "Good Will Hunting" co-star Matt Damon around that same time, her alleged affair with Cusack couldn't have lasted too long. She continues to speak highly of Cusack, describing him as "incredibly intellectually challenging and stimulating and fun" at the 2026 Golden Globes (per People). 

John Cusack starred in a 1997 film called "Midnight in the Garden of Good and Evil." It bombed despite boasting serious Hollywood pedigree, with Clint Eastwood in the director's chair and a star cast that included Cusack, Kevin Spacey, and then-newbie Jude Law. While it wasn't a career highlight for any of the names involved, "Midnight in the Garden of Good and Evil" endured in public memory as the film that became the stage for one of Hollywood's long-forgotten affairs. 

According to the rumor mill, Cusack was briefly involved with Alison Eastwood, daughter of the film's legendary director, at the time. She had a supporting role in the film as Mandy Nichols, the love interest of Cusack's John Kelso. Their on-screen dynamic seemingly spilled over into real life, and while neither star spoke about it publicly, their alleged affair found an eternal place in the legacy of the only film they worked on together.

For the better part of the public speculation that has surrounded his love life for decades, John Cusack has refrained from handing out any solid confirmations or denials. But there is one woman he was linked to for whom he broke his oath of silence: Neve Campbell. Best known for her starring role in the "Scream" franchise beginning in the '90s, Campbell dated the "Serendipity" star for a considerable period at the turn of the millennium.

Years later, in a rare moment of candor about his love life while talking to Howard Stern, Cusack dropped his armor to not just confirm his bygone relationship with Campbell but also fondly ponder over it for a hot second. "[We dated] for a while. She's a gorgeous girl," he said, adding, "It was like 4 or 5 years."

Shutterbugs first started spotting Cusack and Campbell together around Los Angeles in 2000. Campbell, by then, had been divorced from her first husband, Jeff Colt, for a couple of years, and Cusack, as always, had been going steady on his path as one of Hollywood's most elusive unmarried actors. The timing seemed just right for the two stars to connect. From Broadway openings in New York to casual strolls on the streets of Malibu, they accompanied each other everywhere and, though their relationship was reportedly punctuated by breaks, Cusack and Campbell had a good run. They remained friends after the breakup.

The early aughts were a happening time for John Cusack romantically. Or so it seemed, from whatever little tidbits the public and paparazzi could piece together about the famously private star's life. Another name that was thrown up in this regard was Meg Ryan, whom Cusack reportedly dated for a while in 2003. The pair had originally crossed paths a few years prior when they lent their voices to the 1997 animated film "Anastasia," in which their characters were love interests. 

When fate brought them back together in the 2000s, Ryan was going through a turbulent patch in her love life. She had notoriously pursued an affair with her "Proof of Life" co-star Russell Crowe while still married to actor Dennis Quaid, her husband of 10 years. Ryan's image as America's ultimate rom-com sweetheart had already taken a hit in the light of her apparent infidelity, when another layer of speculation surrounding her relationship with Cusack was added to the mix.

"They have amazing chemistry, and the timing was right," a source told Us Weekly at the time, even going on to allege that Cusack was interested in pursuing marriage with the "Sleepless in Seattle" star (via SFGate). Given Cusack's longstanding views on matrimony, the latter claim had already seemed like a stretch when the "Identity" star came forward and dismissed the whole theory. "I couldn't be more single these days," he told The Morning Call. 

The year 2003 was also when Jennifer Love Hewitt joined the ranks of the famous women John Cusack has been linked to in his time as a celebrity. While details about their early noughties dynamic are super scant, the two still find mention on lists of each other's past relationships, making their alleged love affair — no matter how brief or serious — worthy of a mention. 

As indicated by paparazzi photos, it is believed that Cusack and Love Hewitt hung out for a bit in April of that year, notably at the premiere of Cusack's film "Identity" in Los Angeles. Snaps from the event show them delighting in each other's company, with Cusack even playing around with Hewitt's hair in one of them. There is little indication that they dated for too long, though, given that Hewitt's dating records from that time — just as wide-ranging and lively as Cusack's — show that she had other more prominent relationships in 2003 and beyond. 

As someone in the thick of the action, Hewitt made no bones about her grievances with the modern dating scene, telling Blackfilm: "I, in the process of dating, probably do more of the [asking] out than getting asked, because guys do not ask anymore. It's a horrible thing. It just leaves you feeling more hurt when you're the one that kind of goes out and does all the work."

Another of John Cusack's relationships that attracted a lot of attention, or rather, speculation, was the one he allegedly had with Gabriela Spanic, a Venezuelan showbiz star primarily active in Latin television. Unlike his other high-profile liaisons, Cusack's meeting with Spanic did not happen in his Hollywood home turf. According to a report in the Irish Examiner, the two actors crossed paths at a party in the Dominican Republic, and their whirlwind romance unfolded at breakneck speed afterward.

Their brief fling is said to have occurred sometime after Spanic divorced Miguel de León, a Venezuelan star and her husband of seven years, in 2003. On the subject of his ex-wife, León said in an interview at the time: "She has every right to remake her life. If the person she's with right now is going to make her happy, then he's welcome to her world." 

If the rumor mill is to be believed, Spanic began rebuilding parts of her life with Cusack and had allegedly started house-hunting with him as early as 2004. Reports claimed that the duo was also thinking of locking things down with an engagement, which honestly sounded like a stretch even then, considering Cusack's past record and views on marriage. The circumstances under which their relationship ended are not known. 

There was a period in 2003 when John Cusack was frequently spotted out and about on the streets of Los Angeles with film star Jodi Lyn O'Keefe, who was then fresh off her newfound success as a television icon on "Nash Bridges." That career milestone hardly diverted from the widespread interest in her personal affairs; if anything, it only accelerated it. And before long, O'Keefe and Cusack emerged as the noughties' newest celebrity couple. 

Not much spilled out into the public about their tightly guarded relationship, which the two actors apparently kept up for several years, albeit with some breaks along the way. The only memorable account of their love affair surfaced in 2009, when Star Magazine reported that the pair had parted ways (via ONTD). "She desperately wanted to spend the rest of her life with John," an unnamed source was quoted as saying, citing their clashing views on marriage as a reason behind the split. 

While Cusack and O'Keefe never publicly acknowledged their relationship, they continued orbiting each other's lives even long after their purported breakup. In 2012, Cusack was among the celebrity names who attended the launch of O'Keefe's jewelry collection in California. (Another of his alleged ex-flames, Minnie Driver, was also present.) A year later, they co-starred in the 2013 thriller "The Frozen Ground," with O'Keefe telling Cinema Chords, "John Cusack is brilliant and fantastic to work with." 

In what constituted one of his last publicly known relationships, John Cusack seemingly went out with television queen Brooke Burns for a while in the late 2000s. The star of shows like "Baywatch" and "Out of the Blue," Burns was already a hot topic in noughties tabloids — largely owing to her once high-profile relationship with Hollywood icon Bruce Willis — when she was linked to Cusack, who was still riding the wave of success his film "2012" had brought him. 

"They've been going out seriously for more than a month," an unnamed source told Life & Style in 2010 (via Just Jared). They further claimed that Burns had also introduced Cusack to her daughter Madison, whom she shared with actor and ex-husband Julian McMahon, who died in 2025.

Little else emerged about their relationship, the details of which Cusack unsurprisingly kept under tight wraps, save for the age difference between them. While it was nowhere close to some other truly alarming age-gap relationships Hollywood has seen – Cusack was 12 years Burns' senior — it was apparently significant enough for gossip rags to latch onto. It is unclear when or if the relationship ended.