All of Katie Holmes’ Boyfriends

Actress and director Katie Holmes has had quite a love life! Ever since her breakout role on the teen drama Dawson’s Creek, she’s been spotted with a long list of Hollywood hunks. Here is every man 44-year-old Holmes has dated over the past 25 years.

Holmes Dated Her Dawson’s Creek Co-Star Joshua Jackson

Katie Holmes’ character Joey was a hot ticket, too! She had Dawson and Pacey vying for her love throughout the series, with Pacey (Joshua Jackson) coming out on top. In real life, Jackson and Holmes had some serious chemistry — but their relationship was short-lived. In 1998, Holmes told Rolling Stone that she’d fallen in love with somebody one year earlier. She kept his identity private at the time but dropped quite a few hints.

“I fell in love, I had my first love, and it was something so incredible and indescribable that I will treasure it always,” said Holmes. While she went on to imply that they may not exactly be together anymore, she only had wonderful things to say about this mystery guy.

“And that 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.”

Holmes also described her ideal type, which she’s stayed true to dating over the years.

“I’m more apt to go for a dark-haired man,” she said. “I don’t know, it’s my thing. Someone who’s intelligent but not showy. Especially in this business. You get around so many people who always need to be on, and it’s nauseating. It’s like, ‘Would you just be normal?’”

The costars friend-zoned each other by 1999, but they stayed close over the years. At the 20-year Dawson’s Creek reunion, fans thought the two looked “truly, madly, deeply in love.” Jackson even rested his head on Holmes’ shoulder at one point. Allegedly, Woman’s Day went so far as to claim that the two were “finally ready to give their love another shot,” but we’re still waiting to hear how that went.

She Was Once Engaged to Chris Klein

Next in line as Katie Holmes’ suitor was American Pie actor Chris Klein. The two began a long-distance relationship in 2000 — or 1999, depending on the source. Holmes was shooting in North Carolina and Klein was keeping busy in LA, but the pair made it work. Daily Mail reported that Holmes moved to LA to be with Klein after Dawson’s Creek wrapped in 2003. By December of that year, the two were engaged. People claimed the stars had been dating for 5 years at that point, but who knows? By 2005, they called the engagement off.

Klein and Holmes have remained friends over the years despite (or maybe because of) not following through with their wedding. According to HuffPost contributor and former Seventeen writer Deb Baer, there may have been some accidental external factors to their failed marriage plans.

In an article titled “Did I Single-Handedly Ruin Katie Holmes Life?” Baer pointed to a 2004 Seventeen interview with Holmes. News of her engagement to Klein was already made public, prompting Baer to ask, “Are you the kind of girl who’s always dreamed about her wedding day?”

“I think every little girl dreams about [her wedding]. I used to think that I was going to marry Tom Cruise,” Holmes responded. The interview was published in October that year. By March of 2005, her engagement to Klein was called-off. By April, she was dating none other than Tom Cruise, after meeting his a couple weeks earlier, possibly because she was offered a role in Mission: Impossible 3. Coincidence?

Katie Holmes and Tom Cruise Share Daughter Suri

By June of 2005, after only 8 weeks of dating, Holmes had officially switched from Catholicism to Scientology, aligning with Cruise’s faith. A few days later, they announced their engagement after Cruise popped the question on the second floor of the Eiffel Tower.

In October 2005, “TomKat” announced they were expecting a child. Suri was born on April 18, 2006.

In 2012, Cruise gushed to Playboy about his wife, calling her “extraordinary,” and “romantic.”

“I don’t know what to say — I’m just happy, and I have been since the moment I met her. What we have is very special,” he said (via Today).

Holmes didn’t feel the same way, unfortunately. By the summer of 2012, she served Cruise divorce papers and tried to move to New York.

Cruise later acknowledged that one of the reasons Holmes divorced him was to get their daughter away from the Church of Scientology. Because of strict protocol, anyone who ceases practicing the faith becomes essentially ostracized and labeled as a “suppressive person,” minors included. By June of 2016, an insider told In Touch that Cruise hadn’t spoken to or seen Suri in 1,000 days. As of March of 2023, another source told Page Six that the actor has continued to remain estranged from his daughter.

She Secretly Dated Jamie Foxx Before Becoming Semi-Official

Sometime in 2013, Holmes began dating Jamie Foxx. When Entertainment Tonight pressed Foxx on the relationship, he said the rumors were “one hundred percent not true.” He and Cruise had allegedly been friends since filming Collateral together in 2004, so that may have been a little weird.

Holmes and the Back In Action star were spotted in a PDA-filled beach date in September 2017 but still hadn’t made anything official. They finally made a public appearance as a couple at a pre-Grammy party in January of 2018. By December, it became apparent why Foxx and Holmes were trying to keep their relationship on the down low.

Radar Online published an explosive series of claims, stating that insiders had divulged Foxx wanted to “clear the air” with his old pal Cruise about not having an affair with Holmes while they were married. Radar alleged that Foxx and Holmes were considering getting married and that he may even adopt Suri. Alas, none of that came to fruition.

A few months later, Foxx openly told a crowd that he was single. That led to further revelations that he was polyamorous and was urging Holmes to date, other men, if she wanted to. By August 2019, they’d officially split.

She Briefly Dated Chef Emilio Vitolo

In September 2020, TMZ published photos of Holmes on a date with a mystery man at a Mediterranean restaurant in Manhattan. The two were having a fabulous time together.

ET later discovered that Holmes was with the handsome, Italian-Peruvian chef Emilio Vitolo, who is several years younger than she. Vitolo runs Emilio’s Ballato in SoHo.

According to ET, the exact start of Vitolo and Holmes’ fling couldn’t be determined, but he had commented on one of her July Instagram photos. They were seen kissing days later.

By May of 2021, the two had split. A source told People that they were on amicable terms.

“They split several weeks ago. There was no drama,” said the source. “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.”

Another insider told Us Weekly that the ex-lovers were still “friends.”

Bobby Wooten III: Katie Holmes’ Most Recent Boyfriend

Maybe Katie Holmes is totally overdating actors… remember when she detailed her ideal guy to Rolling Stone? After moving on to a chef, her next beau was Grammy-nominated composer, producer, and bassist Bobby Wooten III. People published photos of the couple packing on the PDA as they took a daytime stroll through Central Park in April of 2022. They made their red-carpet debut in May at The Moth’s 25 Anniversary Gala in NYC.

Despite seeming smitten with each other, Holmes and Wooten III called it quits last December.

“Katie and Bobby broke up last week, she’s no longer [talking] about him to his friends,” an insider told Us Weekly. “They just didn’t work out together for the long run.”

Read More: Suri Cruise Lands Role Alongside Mom, Katie Holmes, In New Film ‘Alone Together’