Katie Holmes’ Former Boyfriends Reveal What It’s Really Like to Date Her

Katie Holmes’ much-discussed dating history entered a new chapter in summer 2026, when she was seen with New York artist Jason Bard Yarmosky. The two appeared affectionate during a public outing tied to the premiere of Olivia Wilde’s film “The Invite,” later coordinating navy looks at a four-day Ferragamo pop-up at Bridgehampton’s Topping Rose House. Yarmosky has not commented publicly on the romance, but several of Holmes’ former partners have been far more open about their time with the actor.

Holmes became a household name as Joey Potter on the 1990s teen hit “Dawson’s Creek,” and she has remained a fixture in the public eye ever since. Her career has often shared the spotlight with speculation about her relationships, leaving fans eager to revisit the details of her romantic past. Which former boyfriend says their connection still feels effortless? Who likened their relationship to being the entertainment industry’s prom king and queen? And which comedian joked that he had finally been “cured” of dating white women?

Holmes’ first major romance began with her “Dawson’s Creek” co-star Joshua Jackson. The pair ended their relationship in 1999 but managed to remain on good terms, an important development considering they continued working together for five more seasons. Their fictional characters, Joey Potter and Pacey Witter, would also become a couple on the series. Over the years, both actors have spoken warmly about one another. During a 2025 appearance on the podcast “Dinner’s on Me,” Jackson said they remain connected, even if they do not speak on a regular schedule. “Sometimes it’s not a weekly or monthly or even a half-yearly call,” he said (via E! News). “But when you’re together — there’s always that, ‘I know, you know.’”

In that same year, Holmes and Jackson reunited onscreen as romantic leads in “Happy Hours,” a rom-com directed by Holmes. Jackson expressed genuine excitement about working with his former girlfriend again, recalling the intensity of their early years together and the friendship they maintained afterward. “We spent so much intense time at a particular moment in our lives and then we have maintained our friendship for all of these years, but we’ve never had a chance to be on camera together, and it was magic,” he told Today (via People). He added that it was rewarding to discover they still had chemistry after so much time apart. With the movie reportedly envisioned as the first installment of a trilogy inspired by Richard Linklater’s “Before” films, the former couple may share the screen again.

About three years after her split from Jackson, Holmes began dating Chris Klein, the “American Pie” star known for playing Oz. Their relationship lasted three years, and the couple became engaged before ending things amid intense tabloid attention. During the romance, Holmes was asked by Seventeen about her dream wedding and reportedly said (via InStyle), “I used to think that I was going to marry Tom Cruise.” Her later marriage to Cruise naturally fueled speculation that the two relationships had overlapped.

Klein later rejected that version of events, making clear that Cruise was not responsible for the breakup. “It looked like it was Katie and Chris together and two seconds later Katie and Tom together, but that’s ridiculously compressed,” he told People (via Yahoo! Life). According to Klein, Holmes contacted him directly so he would hear about her decision from her rather than through the media. He also nostalgically described them as “the prom king and queen.” Looking back, Klein remembered a carefree period when both were young actors finding success in late-1990s Hollywood. “We were kids, man,” he told The Daily Beast. “We were all working, successful, and having fun. It was late ’90s, young Hollywood, and we were having a good time … not unlike all those vampires today.”

Holmes’ fame reached another level in 2005, when she began dating Tom Cruise. The relationship drew even greater attention after Cruise’s infamous sofa-jumping appearance on “The Oprah Winfrey Show.” By the end of the following year, Holmes and Cruise had married and welcomed their daughter, Suri Noelle. Cruise was still speaking lovingly about Holmes in 2012, telling Playboy (via ABC News), “She is an extraordinary person. When she walks into the room, I just feel better.” Only a month later, Holmes filed for divorce, prompting a fresh wave of media coverage.

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The former couple issued a joint statement emphasizing their commitment to co-parenting Suri and asking for privacy (via The Guardian). Neither has publicly offered extensive details about the reasons for the split, a silence likely reinforced by the terms of their settlement. Following the divorce, Holmes moved to New York City. In a 2022 interview with InStyle, she recalled walking through the city with her parents and realizing she wanted to live there. “That time was intense. It was a lot of attention,” she said.

After the intense scrutiny surrounding her marriage to Cruise, Holmes became notably guarded about her private life. She never publicly defined her relationship with Oscar winner Jamie Foxx, though the two were photographed together at several events, including the 2019 Met Gala. Their apparent romance remained largely out of the spotlight for roughly six years, but the pair separated not long after that high-profile appearance. Neither ever suggested publicly that marriage was part of their plans.

An insider told People in 2015 that Holmes and Foxx were not pursuing an especially serious relationship, describing them as longtime friends who happened to be single and attractive. Foxx has also avoided directly discussing the romance. However, he sparked renewed tabloid interest with a song in his 2024 Netflix stand-up special, “What Had Happened Was…” During the performance, he joked (via Independent), “Sisters, I’m here to tell you, I’ve been cured. I’ve been cured of everything, no more white girls. I’m serious, no more white girls.”

In 2020, Holmes shifted away from dating fellow movie stars when she became involved with chef Emilio Vitolo Jr. The relationship lasted approximately eight months before ending, though reports characterized the split as calm rather than contentious. “Their relationship fizzled. They figured out they’re better off as friends,” a source told Us Weekly. Their friendly social-media exchange the following year appeared to support that account.

Holmes later thanked Vitolo ahead of the Tribeca Film Festival screening of “Almost a Year,” a pandemic-era short film she co-produced and in which he appeared. Vitolo, who operates New York restaurant Emilio’s Ballato and has also pursued acting, replied with a series of heart emojis. In a 2024 interview with People, he discussed the sudden paparazzi attention that accompanied their romance. “It’s a different animal when you’re in the public eye, you know what I’m saying?” he said. “It did get a little annoying, but whatever. It is what it is. It comes with the territory. It’s almost like a requirement. You become public domain.”

Holmes was linked to musician Bobby Wooten III in spring 2022 after the two were seen kissing during a visit to New York’s Guggenheim Museum. They appeared to confirm the relationship a month later by attending The Moth’s Anniversary Gala together. Wooten was there to present an honor to David Byrne, having played bass in Byrne’s acclaimed production “American Utopia.” Speaking with Us Weekly, Wooten praised Byrne’s influence on his life and added that he was delighted to have Holmes accompany him as his date.

The couple were also seen together at the Tribeca Film Festival, and speculation intensified when Wooten accompanied Holmes during a visit with her mother, Kathleen Ann Stothers-Holmes, in New York. By the end of 2022, however, the relationship had ended. “Katie and Bobby broke up last week; she’s no longer [talking] about him to his friends,” a source told Us Weekly, adding that they ultimately were not a lasting match. Neither Holmes nor Wooten has publicly explained the breakup, leaving the actor’s latest romance with Bard Yarmosky as the newest chapter in her closely watched dating history.