Inside Katie Holmes' Relationship History

There was something undeniably special about the '90s. Any moderately pop culture-obsessed millennial can attest to the fact that it was one of the most exciting eras for fashion, movies, and of course, TV shows. From "Seinfeld" to "The Simpsons," the '90s gave us iconic shows that are popular to this day. It also gave us "Dawson's Creek" — and Katie Holmes.

While the actor made her big-screen debut with Ang Lee's 1997 movie, "The Ice Storm," her role as Joey Potter in "Dawson's Creek" was what propelled her into the spotlight. The show spanned six seasons from 1998 to 2003 during which time Holmes found fame, lifelong friendships, and love. Dubbed a rising Hollywood star, fans expected to see more of the star on screen after the show's end. Although she appeared in several movies and shows, none of them were as successful as "Dawson's Creek." She is loved by fans all the same. In 2016, Holmes made her directorial feature debut with "All We Had" and she continues to make movies.

Career aside, the actor has had a pretty eventful personal life, especially when it comes to the romance department. Though private, her love life has nonetheless played out in the eyes of the public ever since her days as a teen idol. From a dreamy on-set romance to a messy public divorce, her heart has weathered it all. To jog your memory, let's step inside Katie Holme's relationship history. 

Katie Holmes and Joshua Jackson's young love

The first season of "Dawson's Creek" was all about Katie Holmes' Joey Potter falling hard for James Van Der Beek's Dawson Leery. But off camera, she was actually catching feelings for Joshua Jackson, who played Pacey Witter. During an interview with Rolling Stone in September 1998, a 19-year-old Holmes refused to confirm her on-set romance, but did state, "I fell in love, I had my first love, and it was something so incredible and indescribable that I will treasure it always." Per E! News, the couple was thought to have broken up after around a year of dating.

Their romance might have fizzled out, but Jackson wanted a different ending for his character on screen. In May 2022, he told Entertainment Weekly that he desperately wanted Joey to end up with Pacey in "Dawson's Creek." Sadly, the show's creator, Kevin Williamson, was Team Dawson. "I was like 'Hell no! No. No. No. That's not gonna work for me,'" Jackson proclaimed. "I had a whole conversation with Kevin [Williamson] about this. Like 'Look, I get it ... [but] this is the more interesting end for these characters.'" Suffice it to say, Joey chose the one who loved her for who she was.

Moving on from Holmes, the "Fringe" star got back into the dating scene with Diane Kruger in 2006, before breaking up after a decade together. In 2018, he met Jodie Turner-Smith and their one-night stand led to a happy marriage.

She was once engaged to Chris Klein

A year after breaking up with Joshua Jackson, Katie Holmes met "American Pie" star, Chris Klein, and the duo started dating. Naturally, the public was curious about the hip new pair, but the couple kept their relationship pretty low-key. When asked about their relationship by People, Holmes responded, "That's our business. But thank you for wondering." After dating for five years, the two got engaged. However, they parted ways in 2005, just two years after the pair put a ring on it.

In a 2012 interview with People, Klein fondly reflected on the relationship, stating, "We were like the prom king and queen." He added that they parted on fairly good terms. In another interview with The Daily Beast, he shared how their relationship was mostly long-distance and that he would only see Holmes when they took a break from work. "We were kids, man. We met before we could legally drink, so think about when you were 20 to 24, and that's what it was," he reasoned. "We were all working, successful, and having fun." As noted to People, he and Holmes had broken up some time before they'd publicly announced it, which made it seem like Holmes had moved on to her next man far quicker than she actually had. 

Katie Holmes and Tom Cruise's whirlwind romance

As Chris Klein told People, after their breakup, Katie Holmes was kind enough to give him a heads-up about her new relationship — and her next man was none other than Tom Cruise. The "Top Gun" star was one of Hollywood's most desirable men back then, but much to his swooning fans' dismay, the "Dawson's Creek" alum was the one who took his breath away. Interestingly enough, when Holmes was engaged to Klein, she confessed that she dreamt of marrying Tom Cruise when she was a young girl. By some strange coincidence, they started dating seven months later.

The TomKat era started out hot and heavy in April 2005. Right away, the pair seemed to have fallen head over heels in love, with Cruise jumping on Oprah's couch on national TV to celebrate his new girlfriend. After just three months of dating, the "Mission: Impossible" star asked Holmes to marry him with a stunning diamond ring. She obliged. Barely allowing fans to catch their breath, by October the couple had announced they were expecting their first child together. 

It was quite a trip. At least those who questioned the authenticity of their relationship weren't talking anymore. Meanwhile, not only had Holmes made up her mind to marry her couch-jumping beau, but she'd also embraced his controversial religion, Scientology. "I have looked into it myself, and I really like it, and I think it's really wonderful," she told "Access Hollywood" (via E! News).

One of them didn't see a divorce coming

A year after Katie Holmes and Tom Cruise's relationship was made public, Suri Cruise came into the world. She is the third and the youngest child of Cruise who shares two other children, Connor Cruise and Isabella "Bella" cruise, with his ex-wife, Nicole Kidman.

In November 2006, the couple got married in Rome. After seven years of a very public marriage, Holmes decided she wanted out — reportedly from both her marriage and from Scientology. She filed for divorce while Cruise was out shooting "Oblivion" in Iceland, catching him off guard. And while he told ProSieben (via CBS News) that he didn't expect it at all, the star eventually processed it. In fact, Cruise processed it at a record-making rate — his divorce with Holmes was settled within less than two weeks

After Holmes successfully carried out the mission not-so-impossible, People reported that she had been granted primary custody of their daughter. Tom was reportedly in agreement that Suri should be with her mom. But the question remains, why exactly did Holmes run for the hills? Well, she was allegedly trying to keep their daughter away from the Church of Scientology. During his deposition against tabloids that accused him of abandoning Suri after his divorce, Cruise was asked whether it was one of the reasons why Holmes left him. He responded, "Did she say that? That was one of the assertions, yes," per Radar (via HuffPost).

She moved on with Jamie Foxx after the divorce

While Katie Holmes and Tom Cruise's divorce was shrouded in mystery, their fans and the media had theories of their own. Per Radar, there were rumors of an undisclosed divorce agreement between the two. One of the alleged terms was that Holmes wasn't allowed to publicly date anyone for five years following the divorce. Legitimate or not, the unverified report aptly explains why the "Batman Begins" star kept her post-divorce romance with Jamie Foxx on the down low for a little over five years.

The two were first linked in 2013 when they were seen dancing together at a party in East Hampton. Fast forward to 2015, and Us Weekly published photos of them holding hands. Sources told People that the duo had been casually seeing each other for over a year. After multiple public sightings, Holmes and Foxx were said to be engaged in 2016, but Foxx's rep shut down the rumors. The following year, they held hands and frolicked at the beach, never officially confirming their romance. They looked happy and very much in love at Clive Davis's Pre-Grammys Gala honoring Jay-Z in January 2018, and as if the world needed further proof that they were, in fact, an item, Holmes's rep further denied rampant rumors that she and Foxx had broken up. Much to everyone's surprise, Holmes and Foxx were thought to have ended things after attending the Met Gala with coordinated looks in 2019 (via E! News).

Katie briefly dated Emilio Vitolo Jr.

The way to a man's heart is certainly through his stomach. But women also appreciate meals worthy of a chef's kiss that make you fall in love. In Katie Holmes's case, she fell for the man that cooks them and got kisses directly from the source. She and her former flame, chef Emilio Vitolo Jr., were first spotted together in 2020 at his family restaurant, Emilio's Ballato. "Emilio is very charming, flirty. It's easy to see how Katie fell for him," a source told People days after their first sighting. Three months later, the couple celebrated Holmes's birthday together, and Vitolo Jr. commemorated the day with a special Instagram post in which he declared his love for her in the caption, per People.

In the months that followed, Holmes and Vitolo Jr. didn't make much effort to hide their relationship and were often spotted packing on PDA. After nearly a year of dating, the pair broke things off. A source told People that their split was amicable, adding, "It was amazing while it lasted, but they are at very different places in life. Emilio has no hard feelings. His life is in N.Y.C. Katie can't wait to get back to work and to travel again."

Katie Holmes found love with Bobby Wooten III

Katie Holmes has come a long way since her hush-hush romance days with Jamie Foxx and she doesn't seem interested in holding back from flaunting her love life anymore. In April 2022, Holmes was snapped happily strolling about in Central Park with composer, Bobby Wooten III, as they walked arm in arm and kissed passionately. More interestingly, the musician had not only wooed his new boo but her mother, Kathy, too — he was spotted hugging her during their outing which led fans to think that he was more than just another man in Holmes's life. A month later, the couple made their red carpet debut at the Moth Ball's 25th Anniversary Gala. 

Wooten has even met Holmes's daughter, Suri, and she reportedly approves of her mom's new beau. "Suri has always been Katie's number one priority. She has the utmost respect for her daughter and is really conscientious about who she introduces her to," a source told Entertainment Tonight. Even with Suri's stamp of approval, their cute coordinating looks, and all the PDA they pack, netizens continue to wonder if Holmes and Wooten are in it for the long haul. Only time can tell.