Since the ’90s, Katie Holmes‘ romantic relationships have been a topic of fascination among the public. There was her on-set romance with Joshua Jackson while filming Dawson’s Creek, her heavily sensationalized marriage to Hollywood’s No. 1 action star, Tom Cruise, and her secretive relationship with A-list actor Jamie Foxx. And those haven’t been the only men to capture the heart of this brunette beauty, including her most recent boyfriend Bobby Wooten III, 33.
Dawson’s Creek together (the show premiered in Jan. 1998), but the relationship didn’t last for long.
Rolling Stone in 1998, “I’m just going to say that I met somebody last year. I fell in love, I had my first love, and it was something so incredible and indescribable that I will treasure it always…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.”
Their on-set chemistry even came as a surprise to the show’s creator, Kevin Williamson, after he witnessed it while filming the iconic science project episode in Season 1. “Joey and Pacey were paired to do the science project and they had to go and collect samples. They got wet and had to take their clothes off in the truck and there was that very uncomfortable moment where you could just see how she peeked at him and he peeked at her. They were so nervous with each other. They had instant chemistry,” Kevin recalled in a 2018 interview with The Hollywood Reporter.
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Joshua has since married British model Jodie Turner-Smith. After tying the knot in Dec. 2019, they welcomed a baby girl together in April of 2020.
Katie and Chris were an early aughts dream team! While there’s no exact date to pinpoint the beginning of this relationship, Katie became engaged to the American Pie star in 2003 and broke up with 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 exchanged vows the following year. Meanwhile, Katie moved on to her most infamous relationship — more on that below!
“I used to think that I was going to marry Tom Cruise,” Katie, who was then still engaged to Chris Klein, told a Seventeen Magazine reporter in 2004. Ironically enough, her childhood dream came true. Everything happened fast for this duo in 2005: Katie split from Chris, and she made her first public appearance with Tom in Rome in April of that year (Tom was in Italy’s capital to pick up a David di Donatello Award for lifetime achievement).
The very next month, one of the most iconic moments in Hollywood happened: Tom stood up on Oprah Winfrey’s talk show couch and declared his “love” for Katie. By June of 2005, Katie revealed to reporters that she’s converting to Scientology (Tom’s religion) at her big premiere for Batman Begins. In the same month, Tom and Katie became engaged, and announced a child — who would be their daughter Suri Cruise — was on the way!
Suri arrived in April of 2006, and the grand wedding finally happened at the Odescalchi Castle in Bracciano, Italy in Nov. 2006. All seemed picture-perfect until June of 2012, when Katie suddenly filed for divorce from Tom. Even more strange was a report that claimed Katie used “a throwaway cellphone” from a friend to talk to her lawyers and allegedly “hired three law firms in three states” for her divorce case, a source told the Los Angeles Times. Tom even admitted he “didn’t expect” the divorce while speaking with a German TV network called ProSieben in 2013.
Katie ended up with primary custody of Suri, and Tom hasn’t been photographed with his daughter since 2013. Neither parent has explained the situation, either. However, an insider EXCLUSIVELY told HollywoodLife in April of 2019, “As challenging as things have become for him and his daughter, he still loves her. Tom never intended to be estranged from his daughter when he decided to have a family with Katie, and he looks forward to repairing their relationship one day.”
Katie’s next high-profile relationship after Tom was with Ray star Jamie Foxx. However, there was no declarations of love on national TV in this relationship. Katie and Jamie remained very hush-hush after sparking romance rumors because they were seen dancing together at a charity event in the Hamptons in 2013. Jamie even said the romance rumors were “one hundred percent not true” 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 rumored lovers were again seen holding hands in Malibu in 2017. From then on out, it appeared more clear that Katie and Jamie were definitely an item, even if they didn’t care to confirm the relationship in public.
They were pictured out and about on even more occasions, and were even seen 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 came to a halt after May of 2019. Just a few days after Jamie was seen holding hands with singer Sela Vave, it was reported in Aug. 2019 that Katie and Jamie had split.
Emilio Vitolo Jr.
A few months before her 42nd birthday, Katie got fans talking after she was seen cracking up while having a meal with a mystery man in NYC at the beginning of September in 2020. Katie’s handsome lunch buddy turned out to be restaurateur Emilio Vitolo Jr., who owns an Italian restaurant called Emilio’s Ballato in NYC. It didn’t take long for fans to figure out if this relationship was platonic or not, because Katie and Emilio were seen making out during Labor Day weekend in Sept. 2020!
They made no effort of hiding this romance, either, as Katie was pictured sitting on top of Emilio’s lap and kissing him during their dinner date at Peasant Restaurant in Manhattan. Sadly, the romance lasted just eight months as the pair called it quits by May 2021. “The pair have parted ways amicably but remain friends,” a representative for Katie confirmed to Us Weekly.
“Their relationship fizzled. They figured out they’re better off as friends,” an insider revealed to Us. “There’s no drama that went down with the breakup and in fact, they’re still friends. Katie and Emilio really enjoyed their time together — it just simply didn’t work out. She’s focusing on being a mom and her upcoming projects,” they also added.
Bobby Wooten III
Now, we’ve arrived at Katie’s most recent romance! The Dawson’s Creek star was spotted on a romantic afternoon walk with musician Bobby Wooten III in Central Park in April 2022. Since the first sighting of her kissing her new beau, Katie has taken Bobby as her date for plenty of red carpet events, including the Moth Ball Anniversary Gala in May and the Tribeca Film Fest in June.
While the relationship is new, it seems like it’s going really well! While it’s still new, a source close to her revealed to HollywoodLife exclusively that she’s “absolutely smitten” by the bassist. “He is romantic and charming. Katie is allowing herself to feel these feelings and she knows that she is deserving of love,” they said.