Inside Katie Holmes' Dating History

Over the years, we've seen Katie Holmes morph from girl-next-door on "Dawson's Creek" to bona fide Hollywood star and devoted single mom. Alongside this transformation were various partners by her side, albeit at different times.

Joshua Jackson and Chris Klein were her go-to guys for the early part of her career before Holmes somehow did the seemingly impossible and married her longtime Hollywood crush, Tom Cruise, with whom she shares daughter Suri Cruise. Since her divorce, the actress has dated a Hollywood star, a New York City chef, and other creative types. Through it all, though, her daughter has remained the one fixture in her life. "I feel very blessed to have such a special daughter," Holmes said in an interview with Shape. "Being her mom is absolutely the greatest gift and privilege."

From co-stars to other types of creators, let's take a ride down memory lane and go inside Katie Holmes' dating history over the years.

The late '90s teen drama series "Dawson's Creek" was Katie Holmes' first foray into fame. On the show, her character, Joey Potter, is an a love triangle with her longtime best friend, Dawson Leery, played by James Van Der Beek, and his best friend, Pacey Witter, portrayed by Joshua Jackson — off-screen, Holmes and Jackson were even were a thing as well before deciding they were better off as friends. It's no secret that she referenced Jackson in a 1998 Rolling Stone interview. "I'm just going to say that I met somebody last year," she said. "I fell in love, I had my first love, and it was something so incredible and indescribable that I will treasure it always."

Over the years, the two have kept in touch, with Holmes apparently calling Jackson after her 2012 split from Tom Cruise, per Us Weekly, though Jackson was then in a relationship with actress Diane Kruger. In 2018, the twosome reunited for the "Dawson's Creek" reunion. Even then, it was evident they still had major chemistry — and the show's longtime fans were all about it, as BuzzFeed reported.

However, any hopes of them reuniting for real were squashed when Jackson got married in 2019 to actress Jodie Turner-Smith, with whom he shares a daughter. With rumored marital problems, though, we'll keep holding out for a real-life Joey-Pacey reunion.

In the late 1990s and early 2000s, the "American Pie" movies were all the rage — with the first film generating over $235 million worldwide – and Katie Holmes dated one of the franchise's stars: Chris Klein, who played sweet lacrosse player Chris "Oz" Ostreicher. They began dating in 1998 and got engaged in late 2003, managing to keep their relationship details mostly private.

However, barely three months later, the two called off their engagement and broke up, remaining tight-lipped as to the reason. There was speculation at the time that Klein's struggles with substance abuse may have played a role.

In 2012, Klein opened up about his past struggles and where the relationship went wrong. While he said his drinking "didn't help" matters, it wasn't the reason they broke up. "Katie and I were on a journey together" in young Hollywood, he described to People, explaining their similar background and experience. But, he explained, once they began aging out of the teenage scene, their relationship changed. "From my side there was a lot of denial and fear about the future," he said, adding that their breakup was mutual.

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

When Katie Holmes began dating Tom Cruise in 2005, she morphed into an adult mega star seemingly overnight. Their relationship was truly a whirlwind, beginning in the spring of 2005. Cruise wasted no time sharing his excitement for Holmes, as seen from his iconic "Oprah" interview where he jumped up and down on the couch. Interestingly, the actor had been Holmes' Hollywood crush since she was young, which she shared in a 2004 Seventeen interview (via HuffPost).

After two months of dating, Holmes told "Access Hollywood" (via E! News) she planned to study Scientology — Cruise has long been a prominent member of the Church — to prepare to convert. By June 2005, the couple was engaged; by October, they were expecting a baby together, daughter Suri Cruise, born in April 2006. By November, the couple married in Italy.

Holmes once described the marriage to Marie Claire as "exciting" and "fun." Of Holmes, the actor told Playboy (via Today), "She's funny and charming, and when she walks into the room, I just feel better." He added, "I'm just happy, and I have been since the moment I met her. What we have is very special."

However, the fairytale came to an end in June 2012, when Holmes filed for divorce. The actress strategically kept mum, though Cruise later confirmed that Holmes divorced him to protect Suri from Scientology.

After her divorce from Tom Cruise, Katie Holmes and daughter Suri Cruise started a new life for themselves in New York City, with Cruise said to be estranged from his daughter. In October 2014, the single mom opened up to People about their new life for the cover story. "I don't have any fear now, I don't have a lot of rules for myself, and I don't take myself that seriously," she said, explaining she had moved on from the media frenzy that previously was her life. "I don't want that moment in my life to define me, to be who I am. I was an actor before, an actor during and an actor now." The actress' sole focus immediately following the split was on her daughter, who, she said, "means everything to me."

In January 2013, Holmes' rep set the record straight about her love life when Grazia alleged she had been seeing actor Jake Gyllenhall after supposedly being introduced by Holmes' former co-star and onetime boyfriend Joshua Jackson. Reps for all three denied the claims, stating the story was completely false.

Grazia soon launched another unverified story about Holmes, alleging she was seeing jazz musician and pianist Peter Cincotti, who also lived in New York City. Yet again, Holmes' rep quickly shut down the story, telling E! News, "They are not dating."

After a very public relationship with Tom Cruise, Katie Holmes engaged in a private relationship with actor Jamie Foxx. Initially, Foxx denied the dating rumors, telling Nancy O'Dell of "Entertainment Tonight" in October 2013, "It's quite hilarious because we simply danced at a charity event along with a lot of other people."

However, by March 2015, sources confirmed they were indeed spending time together but that they weren't serious. "Jamie and Katie are friends and have been for a long time," a source told People. "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."

By September 2017, the duo confirmed their relationship, openly spending time together on the beach in Malibu, California, per photos obtained by the Daily Mail, which offered an explanation for the couple's super private relationship prior: Allegedly, Holmes' 2012 divorce settlement had prevented her from dating publicly for five years.

But, by August 2019, the couple had already been broken up for several months. Holmes had reportedly initiated the breakup. Foxx did not propose after several years together. Foxx was rumored to have unsuccessfully attempted to rekindle their flame, but the actress had apparently moved on.

In September 2020, Katie Holmes and her new younger man, New York City chef Emilio Vitolo Jr., quickly got hot and heavy. People reported that they would text each other constantly and were seen cozying up to one another often. "Emilio is very charming, flirty. It's easy to see how Katie fell for him," an inside source said. "She seems very into him ... He can't get enough of her attention."

By April 2022, though, their relationship hit a rough patch. "Katie is focusing on upcoming projects and she doesn't have time to see Emilio around the clock," an exclusive source told In Touch. "She feels that their relationship is moving too fast. He really wants to make things work so is giving her some space."

A month later, the two had officially broken up, Us Weekly reported. "Their relationship fizzled. They figured out they're better off as friends. There's no drama that went down with the breakup," a source told the magazine, with another telling People, "They are at very different places in life."

But a report from OK! told a somewhat different story: Holmes had allegedly put the brakes on the relationship because she wasn't sure she could trust him. "Katie started to wonder if Emilio" — who has dreams of becoming an actor — "had ulterior motives for dating her."

It commonly happens that when two Hollywood stars become single, the media decides to pair them together. Katie Holmes was single again after breaking up with Emilio Vitolo Jr. in May 2021. Former Major Leaguer-turned-entrepreneur Alex Rodriguez also had experienced a breakup, splitting from his then-fiancée, Jennifer Lopez, in April 2021 after a lengthy relationship.

So, when Rodriguez was seen leaving Holmes' fancy Manhattan high-rise one Sunday that spring, the rumor mill went wild. However, Holmes' rep quickly put a stop to it, telling Radar Online that the two "have never even met." Both Holmes and Rodriguez denied the claims, with Page Six reporting that A-Rod just happened to be in the actress' apartment building because he was looking for a new place in New York City. As an inside source close to the former New York Yankees shortstop told the outlet (via Radar Online), "Alex is looking at lots of different apartments, he didn't even realize it was Katie's building — he's never met her."

A year after breaking up with Emilio Vitolo Jr., Katie Holmes was seen in New York City putting on the PDA with Bobby Wooten III, a Grammy-nominated musician and adjunct instructor at New York University's Tisch School of the Arts. In April 2022, the two were also spotted out and about with Holmes' mom, Kathy Holmes, an unofficial confirmation that the two were an item. In May, the couple made their first official public appearance in New York City as a couple.

In June 2022, Holmes spent time with Wooten's family when she was his date for his close friend's wedding. "Whenever they would go without seeing each other, they would kiss and be very happy to be together again," a inside source told Us Weekly. "Katie and Bobby were very affectionate with each other at all times; they looked very in love and didn't care who saw."

Sadly, by December 2022, sources confirmed that the two had broken up, telling Us Weekly, "They just didn't work out together for the long run."