Every Star She’s Dated Over the Years – Hollywood Life

Every Star She’s Dated Over the Years – Hollywood Life

Katie Holmes is an actress who rose to fame while appearing in Dawson’s Creek in 1998. She was previously married to actor Tom Cruise from 2006 to 2012. The beauty is reportedly single again as of December 16, 2022.

Since the ’90s, Katie Holmes’ romantic relationships have been a subject of public fascination. There was her on-set romance with Joshua Jackson while filming Dawson’s Creek, her highly publicized marriage to Hollywood’s #1 action star Tom Cruise, and her secret relationship with A-list actor Jamie Foxx. And they weren’t the only men who have captured the brunette beauty’s heart, including her latest boyfriend Bobby Wooten III, 33, who she reportedly split from in December 2022.

In chronological order, we look back at Katie’s greatest relationships – starting with Joshua and ending with her most recent breakup! Katie is never single for long and based on the Batman Begins star’s impressive IMDb portfolio and good looks, we can see why.

Joshua Jackson

Everett Collection/Columbia TriStar

Behind the chemistry you saw between one of TV’s most famous couples, Joey (Katie) and Pacey (Joshua), there was real love! The co-stars eventually began dating after filming the earlier episodes of Dawson’s Creek together (the show premiered in January 1998), but the relationship didn’t last long.

While she didn’t name names, it was heavily implied that Katie was talking about Joshua when she told Rolling Stone in 1998, “I just want to say I met someone last year. I fell in love, I had my first love, and it was something so incredible and indescribable that I will always cherish… And that I feel so lucky because he’s one of my best friends now. It’s weird, it’s kind of like a Dawson and Joey thing now.”

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Her on-set chemistry even surprised series creator Kevin Williamson after he witnessed her filming the iconic Season 1 episode of The Science Project Collecting Samples. They got wet and had to undress in the truck and there was this very awkward moment where you could only see her looking at him and he looking at her. They were so nervous with each other. They had chemistry right away,” Kevin recalled in a 2018 interview with The Hollywood Reporter.

Joshua has since married British model Jodie Turner-Smith. After tying the knot in December 2019, they welcomed a baby girl together in April 2020.

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Chris Klein

Every Star She’s Dated Over the Years – Hollywood LifeAP images

Katie and Chris were an early childhood dream team! Though there’s no specific date to pinpoint when this relationship began, Katie got engaged to the American Pie star in 2003 and split from him in 2005 after a “five-year relationship,” according to People. Chris later became engaged to Laina-Rose Thyfault (who works in casting) in 2014 and they tied the knot the following year. Meanwhile, Katie moved on to her most notorious relationship – more on that below!

Tom cruise


“I used to think I was going to marry Tom Cruise,” Katie, then engaged to Chris Klein, told a reporter for Seventeen Magazine in 2004. Ironically, her childhood dream came true. In 2005 things happened quickly for this duo: Katie split from Chris and made her first public appearance with Tom in Rome in April of that year (Tom was in Italy’s capital to accept a David di Donatello award for lifetime achievement).

The very next month, one of Hollywood’s most iconic moments happened: Tom got up on Oprah Winfrey’s talk show couch and declared his “love” to Katie. In June 2005, Katie revealed to reporters that she was converting to Scientology (Tom’s religion) at her big premiere for Batman Begins. That same month, Tom and Katie got engaged and announced that a child – who would be their daughter Suri Cruise – was on the way!

Suri arrived in April 2006 and the big wedding finally took place in November 2006 at Odescalchi Castle in Bracciano, Italy. Everything seemed perfect until June 2012, when Katie suddenly filed for divorce from Tom. Even stranger was a report that claimed Katie used “a disposable cell phone” from a friend to talk to her attorneys and allegedly hired “three law firms in three states” for her divorce case, a Los Angeles source said Times with. Tom even admitted he “didn’t expect” the divorce while speaking to a German TV station called ProSieben in 2013.

Katie ended up with sole custody of Suri, and Tom has not been photographed with his daughter since 2013. The parents did not explain the situation either. However, an insider told HollywoodLife EXCLUSIVELY in April 2019, “As challenging as things have gotten for him and his daughter, he still loves her. Tom never intended to be estranged from his daughter when he decided to start a family with Katie and he looks forward to one day restoring their relationship.”

Jamie Foxx


Katie’s next high-profile relationship after Tom was with Ray star Jamie Foxx. However, in this relationship there were no declarations of love on national television. Katie and Jamie have kept very quiet after sparking romance rumors because they were spotted dancing together at a charity event in the Hamptons in 2013. Jamie even said the romance rumors were “one hundred percent untrue” in an interview with Entertainment Tonight in October of that year.

However, they were secretly photographed holding hands in 2015. The public didn’t see another PDA photo until 2017, when the alleged lovers were spotted holding hands again in Malibu in 2017. From there, it seemed clearer that Katie and Jamie were definitely an item, even if they didn’t want to publicly confirm the relationship.

They’ve been out and about even more, and were even spotted together at Clive Davis’ 2018 Pre-Grammy Gala in New York City. After a long string of paparazzi photos, the couple finally attended their first public event together at the 2019 Met Gala (they didn’t walk the red carpet together though).

Photos of the duo died down after May 2019. Just days after Jamie was spotted holding hands with singer Sela Vave, it was reported in August 2019 that Katie and Jamie had split.

Emilio Vitolo Jr.

A few months before her 42nd birthday, Katie got fans talking after she was spotted dining with a mystery man in New York in early September 2020. Katie’s handsome lunch pal turned out to be restaurateur Emilio Vitolo Jr., who owns an Italian restaurant in NYC called Emilio’s Ballato. It didn’t take long for fans to find out if this relationship was platonic or not, as Katie and Emilio were spotted snogging on Labor Day weekend in September 2020!

Katie Holmes & Emilio Vitolo Jr.Katie Holmes and boyfriend Emilio Vitolo Jr. didn’t shy away from PDA. (MEGA)

They didn’t bother trying to hide this romance either, as Katie sat on Emilio’s lap and kissed him during their dinner at the Peasant Restaurant in Manhattan. Sadly, the romance only lasted eight months as the couple called it quits in May 2021. “The couple have amicably split but remain friends,” a Katie rep confirmed to Us Weekly.

“Their relationship fell apart. They’ve found that they’re better off as friends,” an insider tells us. “There was no drama ending with the split and in fact they are still friends. Katie and Emilio really enjoyed their time together – it just didn’t work out. She’s focused on being a mom and her upcoming projects,” they added.

Bobby WootenIII

katie homes dating history ss post2 News For Everyone Zoohouse NewsBobby accompanied Katie to a few red carpet events early in their relationship. (John’s PKI / SplashNews.com)

Now we come to Katie’s latest romance! The Dawson’s Creek star was spotted taking a romantic afternoon stroll with musician Bobby Wooten III in Central Park in April 2022. After Katie first saw her kissing her new boyfriend, Katie took Bobby as a date to numerous red carpet events, including the Motte Ball anniversary gala in May and the Tribeca Film Fest in June.

At the beginning of the relationship things seemed to be going really well! A source close to her exclusively revealed to HollywoodLife that she was “absolutely smitten” with the bassist. “He’s romantic and charming. Katie allows herself to feel those feelings and she knows she deserves love,” they said. Sadly, on Dec. 16, 2022, Bobby and Katie decided to go their separate ways after dating for less than a year, according to US Weekly. “Katie and Bobby broke up last week, she isn’t anymore [talking] through him to his friends,” the source at the time told the outlet. “They just didn’t work together over the long term.”

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