Katie Holmes' Ex-Boyfriends Have A Lot To Say About Her

Katie Holmes' colorful love life took yet another turn in the summer of 2026 when she stepped out with Jason Bard Yarmosky, an artist from New York City. The pair engaged in several public displays of affection while appearing to launch their relationship at a showing of the Olivia Wilde film "The Invite." They also co-ordinated their navy outfits while attending a four-day pop-up Ferragamo store at Bridgehampton's Topping Rose House. While Yarmosky has yet to speak about their burgeoning romance, plenty of Holmes' past suitors have gladly opened up about their experiences dating and splitting from the star.

Holmes launched to fame thanks to her role in the '90s teen drama "Dawson's Creek," and she's been in the spotlight ever since. Indeed, Holmes regularly makes the headlines, though not always for her work as an actor. When it comes to catching up on all the intimate details and rumors surrounding Holmes' love life, fans and critics alike simply cannot get enough. So, which ex-boyfriend believes they still have a natural chemistry? Which ex compared their three-year stint together to being prom king and queen? And which comedian joked that they're now cured of dating white girls?

The truth about Katie Holmes' first notable relationship was that it all began with her "Dawson's Creek" co-star Joshua Jackson. Luckily, the pair remained amicable once they split in 1999: after all, they'd have to share the screen for another five seasons and their characters, Joey Potter and Pacey Witter, also became romantically involved. In fact, they've had nothing but positive things to say about each other ever since. While guesting on podcast "Dinner's on Me" in 2025, Jackson confirmed they're still very much part of each other's lives. "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.'" 

That same year, they played love interests in "Happy Hours," a rom-com also directed by Holmes. And Jackson couldn't have been more stoked to share the screen again with his ex. "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 gushed to Today (via People). "[Y]ou never know until you're actually doing the thing, but to still have chemistry with somebody after all of those years is nice." And with the project planned to be the first part of a trilogy a la Richard Linklater's "Before" series, they may get the chance to rekindle this chemistry twice again.

Three years after splitting from Joshua Jackson, Katie Holmes entered into a relationship with Y2K heartthrob Chris Klein, aka lovable jock Oz in the "American Pie" franchise. The pair spent three years together and even planned to marry before calling off their engagement amid a wave of tabloid speculation. Indeed, when asked by Seventeen about her ideal wedding during their time together, Holmes answered (via InStyle), "I used to think that I was going to marry Tom Cruise." Inevitably, tongues started wagging when she later did just that. 

However, Klein insisted that the "Top Gun" star had nothing to do with their break-up. "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). "Kate was incredibly respectful about the decision she was making to move on. She called and said, 'Listen I want you to know before you see it anywhere else.'" In the same interview, Klein said, "We were like the prom king and queen." According to Klein, he looks back with fondness on their time together, when they were the new kids on the block in the entertainment world. "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."

Katie Holmes' public profile skyrocketed in 2005 when she started dating superstar Tom Cruise, even more so after his sofa-jumping antics on Oprah Winfrey's daytime show — one of Cruise's Tom's wildest interviews to date. And at the end of the following year, by which point they'd also welcomed daughter Suri Noelle into the world, they became husband and wife. In 2012, Cruise still appeared to be head over heels for Holmes, telling Playboy (via ABC News), "She is an extraordinary person. When she walks into the room, I just feel better." However, just a month later, the "Dawson's Creek" favorite filed divorce papers, inevitably sending the tabloids into another frenzy.

The pair subsequently released a joint statement, which read (via The Guardian), "We are committed to working together as parents to accomplish what is in our daughter Suri's best interests. We want to keep matters affecting our family private." No doubt thanks to a water-tight settlement, neither party has publicly spoken about each other regarding the personal details of the decision since. After the divorce, Holmes packed up and moved to New York. "I remember walking the city with my parents after dinner one night and thinking, 'I need an apartment here. I need to be here,'" she told InStyle in 2022 of the big move post-divorce. "That time was intense. It was a lot of attention."

Understandably, after all the Tom Cruise drama, Katie Holmes has decided to keep quiet about her personal life ever since. In fact, she never once publicly spoke about the nature of her relationship with Academy Award winner Jamie Foxx. But with the fact they showed up arm-in-arm on the red carpet of several events, including the high profile Met Gala in 2019, it seems fair to surmise that they were once an item. In fact, Holmes and Foxx managed to keep things on the relative down-low for a good six years. But despite this lengthy period, it doesn't seem as though marriage was ever on the cards, as Foxx and Holmes split not long after the Met Gala.

"This is not some intense romance," an insider told People in 2015. "Jamie and Katie are friends and have been for a long time. They are two adults who are attractive and single, and so apparently conclusions will be drawn. But contrary to those conclusions, they're not about to run off and make some serious commitment." Foxx has also never explicitly discussed his time with Holmes. However, the comedian gave the tabloids some ammunition with a musical number performed in the 2024 Netflix stand-up film "What Had Happened Was..." In the special, he told the audience (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." Here's a timeline of Jamie Foxx's relationships. 

Following a string of failed relationships with high-profile actors, Katie Holmes changed tact in 2020 when she began dating a man better known for being a chef, Emilio Vitolo Jr. Unfortunately, this new approach didn't result in a happy ever after, either. They split up after just eight months. However, there doesn't appear to have been any major drama between the pair. "Their relationship fizzled. They figured out they're better off as friends," an insider told Us Weekly. Both parties appeared to confirm that their separation had been entirely amicable with a 2021 exchange on social media. 

Indeed, Holmes thanked Vitolo Jr. ahead of the Tribeca Film Festival premiere of "Almost a Year," a pandemic-themed short film co-produced by the former and co-starring the latter. Yes, as well as running swanky New York eatery Emilio's Batalo, Vitolo Jr. is also an aspiring thespian. In response, he posted six heart-shaped emojis. In a 2024 interview with People, the multi-talent also discussed the experience of being followed by the paparazzi during his brief spell with Holmes. "It's a different animal when you're in the public eye, you know what I'm saying?" he remarked. "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."

Katie Holmes got tongues wagging in the spring of 2022 when she was spotted locking lips with multi-instrumentalist Bobby Wooten III while visiting the Guggenheim Museum. And they appeared to make things official a month later when they hit the red carpet together at The Moth's Anniversary Gala. Wooten was in attendance to give an honorary award to musical maverick David Byrne: He'd played the bass in the Talking Heads frontman's critically acclaimed show, "American Utopia." "He's impacted my life like crazy so it's quite easy to speak on everything he's done for me," the musician said to Us Weekly. However, he seemed just as excited about the woman on his arm. "I'm happy to have [Katie] here as my date," he beamed.

The couple also enjoyed each other's company at the Tribeca Film Festival and things appeared to have gotten serious when they were seen visiting Katie's mom, Kathleen Ann Stothers-Holmes in New York. However, by the end of the year, they'd decided to part company. "Katie and Bobby broke up last week; she's no longer [talking] about him to his friends," a source claimed to Us Weekly. "They just didn't work out together for the long run." And both parties have kept schtum about the reason for their split. As with most Hollywood stars, Katie's eventful love life doesn't stop there. Check out Katie's age-gap relationship with Bard Yarmosky.