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When you ponder Katie Holmes’s big relationships, Tom Cruise is the first guy to spring to mind — well, after Dawson and Pacey, anyway. But before her six-year marriage to Cruise, the actress was engaged to Chris Klein, also a pretty face on the teen scene. Let’s look back and try to figure out whether he was the one who got away or just ancient history …
How It Began
These two got famous at around the same time: Dawson’s Creek, which Holmes starred in as Joey Potter, premiered in 1998, while Klein became a teen pinup in 1999 thanks to his role in American Pie.
Holmes had recently split from Joshua Jackson, whom she calls her first love — she told Rolling Stone their relationship was “something so incredible and indescribable that I will treasure it always” — when she and Klein crossed paths and fell in love. It was the year 2000, and they were both just 21. (The pair, both now 46, are only three months apart in age.)
How Long It Lasted
Five years! A long time for two kids starting out in Hollywood. Actually, though, Holmes wasn’t in Hollywood much — Dawson’s Creek was shot in Wilmington, North Carolina, so the first half of their relationship was largely long-distance. “We certainly don’t see each other as much as we’d like, but we try to use the time that we have to the best of our advantage,” she told People in 2002.
When Dawson’s wrapped in 2003, Holmes moved back to Los Angeles, and the couple got engaged during the Christmas holidays that year. But the wedding never happened: In March 2005, their split was confirmed.
How It Ended
During her engagement to Klein, Katie “joked” to Seventeen magazine, “I used to think that I was going to marry Tom Cruise.”
And we all know what happened next: Just weeks after the split from Klein was confirmed, Holmes was deep in a whirlwind romance with her former heartthrob, resulting rapidly in marriage, a daughter (Suri, now 19) and, after six years, divorce.
The picture that was painted at the time was one in which Klein was dumped for Cruise — but he says that wasn’t the case, and they actually split a few months before it became public knowledge. Either way, it was an awkward couple of years there for Klein, with him even being forced to deny wild rumors that Suri was actually his child.
What They Said About Each Other
Both parties were pretty coy during their relationship, with Holmes telling reporters in 2003, “Things are very good. Thank God.” When asked whether they were cohabiting, she replied, “That’s our business. But thank you for wondering.”
In November 2005 — just a few months after the breakup, but with Holmes already pregnant with Suri — Klein spoke to Details magazine about what had gone down. “Her being with Tom has nothing to do with her and I discontinuing our relationship,” he said. “People move forward, people move on, it’s what we do. We grew up. The fantasy was over, and reality set in. We weren’t lighting each other’s fire anymore.”
He added: “For me, what we had was very, very special and I hope that she’s making decisions that are making her happy and that she doesn’t have people in her life leading her astray from what she wants and what she believes.”
Around the same time, he also told AP Radio that he wouldn’t be reaching out to Holmes and Cruise to offer his congratulations. “Her and my relationship is a time in the past,” he said. “And it’s a time that I’ll always look back with in fondness, but her and I have moved on, and she has a separate life and I have a separate life. And it’s better that we keep it that way.”
Holmes was less open about the breakup but was quoted by Page Six in 2005 as saying she had no regrets. “I guess what I’ve learned is that it’s OK to have big dreams and not be embarrassed or apologize for it,” she reportedly said.
What They Say Now
Years after the split, in 2012, Klein spoke to People magazine about the relationship — and breakup — that still had everyone intrigued. “Katie and I were on a journey together … we were like the prom king and queen,” he said. “We had a similar upbringing and we were going through the same experience. We were kids, man. We met before we could legally drink.”
He added: “We were all working, successful, and having fun. As the teenage craze came to an end, we found that our relationship was changing as well. From my side there was a lot of denial and fear about the future. It ended as amicably as these things can end. When we were breaking up, we kept it to ourselves for a while. It looked like it was Katie and Chris together and two seconds later Katie and Tom together, but that’s ridiculously compressed. … Katie was incredibly respectful about the decision she was making to move on.”
Key Relationship Takeaways
Holmes and Klein’s split just seemed like two twentysomethings deciding their relationship had run its course — until the Tom Cruise factor made everything feel a little more complicated. No matter how amicable their breakup was, it can’t be easy when your ex settles down with the guy whose face she used to have pinned to the wall of her teenage bedroom.
Despite all this drama, Klein and Holmes are now on good terms, with sources telling Heat magazine in 2012 that Klein was one of Holmes’s “few really solid friends.”
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Life is going well for Klein now too. “It’s been a journey,” he exclusively told Us Weekly in May 2025 while promoting his movie Fear Street: Prom Queen. “I’m finally at a place in my career where these parts are becoming available to me. Directors and studios and wonderful producers … are starting to see me in [certain roles] a little bit more than they would’ve, and rightfully so, earlier in my career.”
The actor has now been married to wife Laina Rose Thyfault for a decade, with the couple sharing son Frederick, 9, and daughter Isla, 7.
Meanwhile, Holmes’ biggest relationship after Klein and Cruise was with Jamie Foxx, but the couple split in 2019, and she hasn’t been super serious with anyone since.
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