Before their iconic characters Pacey and Joey got together on-screen, the Dawson's Creek co-stars date for from 1998 to 1999. "I'm just going to say that I met somebody last year," Holmes coyly told Rolling Stone in 1998. "I fell in love, I had my first love, and it was something so incredible and indescribable that I will treasure it always."
When asked if she was referring to Jackson, the magazine reported the then-19-year-old buried her face in her hands before saying, "I feel so fortunate because he's now one of my best friends. It's weird. It's almost like a Dawson-and-Joey type thing now. He's been in the business so long, and he's really helped me. I respect him as a friend and as a professional."
Alas, the couple broke up, though they remained friends throughout the iconic WB series' six-season run.
Two years after her romance with Jackson ended, Holmes began dating the American Pie star. The pair got engaged in December 2003, but Holmes ended the relationship less than two years later—and just a few months before the TomKat era began.
To end any speculation about the timeline of the actress' engagements, Klein told Access Hollywood at the time, "People are going to write what they want to write. Her being with Tom has nothing to do with her and I discontinuing our relationship."
Holmes, meanwhile, told W Magazine, "Chris and I care about each other and we're still friends. Tom is the most incredible man in the world."
Klein would reflect on their relationship in a 2012 interview with People, explaining, "We found comfort in one another. We had a similar upbringing, and we were going through the same experience. As the teenage craze came to an end, we found that our relationship was changing as well."
He continued, "From my side there was a lot of denial and fear about the future. It ended as amicably as these things can end."
In April 2005, Holmes became one-half of one of the decade's most infamous celebrity couples, beginning a very public whirlwind romance with the movie star, who was 16 years her senior. She overtly gushed about Cruise—her former childhood crush who was once plastered on her bedroom wall—in interviews. He jumped on Oprah Winfrey's couch to declare his love. They announce they were expecting their first child six months into their relationship and Holmes gave birth to their daughter, Suri, in April 2006.
Their straight-out-of-a-movie love story was bookended by a lavish $3 million Italian wedding (that boasted multiple bridal gowns, a serenade by Andrea Bocelli and guests like Will Smith and Jada Pinkett-Smith, John Travolta, Victoria and David Beckham and Jennifer Lopez) and the first family photo was splashed across the cover of Vanity Fair.
All was well...
But five years after tying the knot, the fairy tale seemed to be over and Holmes shocked the world by filing for divorce. "Tom is deeply saddened and is concentrating on his three children," Cruise's publicist told E! News in June 2012. "Please allow them their privacy."
Holmes' divorce attorney also issued a statement: "This is a personal and private matter for Katie and her family. Katie's primary concern remains, as it always has been, her daughter's best interest."
After gaining a reputation as one of the most public celebrity couples, Holmes and Cruise's split became of Hollywood's most private and their divorce was finalized in less than two months.
While they lost touch after Dawson's Creek ended its run in 2003, Holmes and Jackson reconnected in 2012, just after her split from Cruise, with Jackson revealing details during an appearance on Canadian talk show George Stroumboulopoulos Tonight. "Yeah, actually, like any old friend, it was like, 'Oh, hi how are ya? What's going on?' 'I had a kid,'" Jackson said. "It was very nice, actually."
The former couple once again reunited when they participated in Entertainment Weekly's cover story for the show's 20th anniversary in 2018.
In January 2013, Italian tabloid Grazia reported that Holmes was secretly dating the End of Watch actor, with the story going on to claim Joshua Jackson had set them up. Alas, it was basically fan-fiction, with Holmes' rep telling E! News, "This story has not one ounce of truth." Meanwhile, Gyllenhaal's rep said, "It's a complete fabrication."
And for good measure, Jackson's team added, "There is no truth to any part of this story."
Shortly after the debunked Gyllenhaal rumors, the First Daughter star once again was making headlines in Grazia for an alleged new relationship, this time with the jazz musician. Once again, the mag's reporting was denied. "They are not dating," Holmes' rep told E! News.
A year after her divorce, speculation about Holmes and the Oscar winner—who starred opposite Cruise in 2004's Collateral—quietly coupling up began when they were photographed together in the Hamptons. At the time, however, Foxx shot down the rumors, telling Entertainment Tonight that they were "100 percent not true. In fact, it's quite hilarious because we simply danced at a charity event along with a lot of other people."
But in the years that followed, the private pair continued to fuel romance speculation with sightings in Miami, New York City and Los Angeles. And the pair made a massive statement by posing for photos together at the 2019 Met Gala, seemingly confirming their romance.
A few months later, a source told E! News that Holmes and Foxx had broken up shortly after the high-profile appearance. This news emerged days after the Just Mercy star was spotted holding hands with singer Sela Vave outside of a nightclub in West Hollywood. (Foxx later set the record straight, defending Vave, then 21, from "home wrecker" claims.)
Both parties have never spoken publicly about their mysterious six-year relationship, but an insider told People the split was amicable. "It ran its course," the source explained. "This industry is very tough on relationships. Jamie thinks Katie is an incredible human being. They had a very, very deep connection. They brought each other a lot of joy and laughter."
Over Labor Day Weekend, The Secret: Dare to Dream star was photographed enjoying a dinner date with the NYC chef. The couple weren't shy when it came to PDA, passionately kissing throughout their meal and Holmes was snapped sitting on the restaurateur's lap. They've since been photographed dining and making out around the city.
The 33-year-old was previously engaged to designer Rachel Emmons, InTouch Weekly reported. A source told the publication the two "broke off their engagement very recently" because Emilio is "focusing on his restaurant." (He and Rachel were last photographed together on Aug. 23.)