Throwback Hollywood Couples: Britney Spears, Kevin Federline, Kim Kardashian

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Kate & Dax

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The former flames discussed their 2007 whirlwind romance and why it fizzled out during an episode of Armchair Expert with Dax Shepard.

After first meeting in Tobey Maguire's backyard, the two immediately hit it off and then reconnected a year later at a restaurant in Malibu. The actors decided to pull a prank on paparazzi, who were waiting outside the restaurant at the time, and pretended to leave as a couple. The prank led to Hudson and Shepard testing the waters as a real-life couple but after a few months, they both realized that they were better off as friends.

Not long after calling it quits, Shepard went on to meet his now-wife Kristen Bell. The couple got married in 2013 and currently share two daughters, Delta and Lincoln.

Hudson is currently dating Danny Fujikawa, and the pair welcomed their first child — and Hudson’s first daughter — Rani Rose in October 2018.

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Carrie & John

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Dancing with the Stars judge Inaba sat down on The Talk, revealing that she and the Full House star previously dated years ago.

“We did date. When I was a ‘Fly Girl,’ the dreamiest thing happened. Somebody was like, ‘Somebody wants to meet you across the room.’ The room parted and on the other side of the room was John Stamos,” she shared.

“It didn’t quite work out because I was not quite ready for somebody as good as John Stamos in my life at that moment,” she said. “And so, I pushed him away, and then I was like, ‘Uh oh, that wasn’t a good idea’ … so I went back to his house and I was outside on his driveway with a little note in his mailbox.”

Despite her attempt at reconciliation, Inaba said they “didn’t get back together” — but the pair is on good terms now.

“Later on, he came to Dancing with the Stars and he’s so cool because he knew I was embarrassed and he was performing and he came right up to me and said, ‘I’m so happy for your success. I wish you all the best. It’s great to see you.’

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Katy & Josh

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During a chat on a September 2018 episode of Watch What Happens Live, Groban revealed that not only did he date Perry, but her song "The One That Got Away" is allegedly about him.

"I was not expecting that,” he said. "That was a double take and a spit of my coffee when I saw that."

Of their past relationship, he said, "We were both very private and we realized we were better as friends and we’ve been very, very good friends to this day. She’s the best."

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Nicole & Lenny

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Kidman recently revealed that she was once engaged to the rocker, whom she dated in 2003. "It just wasn't right," she told Vanity Fair in 2007 about her then-secret former fiancé. "I wasn't ready. We weren't ready." Now, Kidman is starring alongside Kravitz's daughter Zoë in the HBO miniseries Big Little Lies. "Well, I knew Zoë because I was engaged to her father. It's all in the family," she told The EDIT, adding, "I love Lenny; he's a great guy." The one-time lovebirds reunited backstage at the 2016 CMT Music Awards, where they posed for sweet pictures alongside Kidman's husband Keith Urban.

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Jenna & Justin

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The former backup dancer confirmed that she and the "Sexyback" singer were briefly involved with each other long before falling for their respective spouses. "I was dancing with him after the breakup [with Britney Spears] — like during, after the breakup," Dewan explained on Watch What Happens Live. "We dated," she went on to admit. "[It was] not that long. We were like friends that then dated … We're still good friends. It's not as salacious as everyone thinks." The actress also made a point of clarifying that she was not Timberlake's "rebound chick" after he ended things with the princess of pop.

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Jessica & Chris

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Before she was truly in sync with Justin Timberlake, the actress cozied up with the man we all now know as Captain America. Biel and Evans began dating in the early 2000s and broke up in 2006. Before the split, the pair starred together in 2004's Cellular and 2005's London.

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Kirsten & Jake

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Dunst and Gyllenhaal dated from 2002 to 2004, after they were introduced by the actor's sister, Maggie. The couple shared a Los Angeles home and adopted a puppy together before the breakup.

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Winona & Matt

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Once Hollywood's “It" couple, Ryder and Damon began dating in 1997 after being introduced by Gwyneth Paltrow at a New Year's Eve party. Their relationship ended in 2000.

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Shia & Rihanna

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Rihanna and LaBeouf were spotted sharing a meal in summer 2007. "It never got beyond one date," the actor told Playboy in 2009. "The spark wasn't there. We weren't passionate about each other in that way, so we remain friends."

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Sarah & Robert

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Parker and Downey Jr. dated for seven years after meeting on their 1984 film Firstborn. The relationship had a lasting effect on the actress, who in 2016 told PEOPLE, "It taught me how to love … And what's the difference between loving and taking care of people and what's necessary, and what grown-ups should and shouldn't do for one another." Parker even said that Downey Jr., who struggled with substance abuse during their time together, helped prepare her for parenthood: "Maybe it taught me a little bit about being a parent too, because the things that I ended up caring about, and the way I cared for Downey, were things that might be more suitable for a parent at a certain point."

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TOPHER & IVANKA

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BlacKkKlansman actor Topher Grace relived memories of his early 2000s relationship with President Donald Trump's oldest daughter when a reporter for the Daily Beast asked him if it was true.

"Uh… I did. Certainly, it wasn’t a political statement," Grace said. "This was a decade ago. I met her here in New York and we went on a couple of dates. I wouldn’t say that we ‘dated,’ but… I didn’t do it for political reasons."

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GIGI & CODY

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Before there was Zigi, we looked to Simpson and Hadid to redefine all of our relationship goals. (The model was even featured in his “Surfboard” music video!) The pair split in 2015.

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BRITNEY & KEVIN

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There was a time – some 40 hours after their September 2004 surprise wedding, to be specific – when Spears and Federline were way busy exchanging "oh babys," gazing into each other's eyes and locking bare toes, as one does when in love. "That time, it's like a whirlwind," Federline, who's dedicated to co-parenting their two sons following their 2006 split, told Access Hollywood in a March 2015 interview. "It was a good time in my life."

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NICK & KIM

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Yes, they were only briefly linked in 2006 ("We went to a movie," Lachey would later recall). Yes, they're now both happily married. Yes, there's a piece of our hearts that will always be missing – just think about the reality show that could have been.

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RYAN & SANDRA

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Sometime between establishing himself as a formidable dance genius and a meme – from 2002 to 2003, to be exact – Gosling dated his Murder by Numbers costar Bullock, who's his senior by 16 years.

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NICK & MILEY

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After dating on and off starting in 2006, Cyrus and Jonas just couldn't twerk, ahem, work through their issues. "Nick and I loved each other," a 15-year-old Cyrus recalled in 2008. "For two years, he was basically my 24/7." And while they've both moved on, we're comforted by the fact they've both developed a similar reputation for not wearing clothes.

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ALANIS & RYAN

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Dear Drew Barrymore, thank you for uniting these lovebirds at your birthday party in 2002. Although they would go on to call off their engagement in 2007, we'll always cherish the time we shared with Reynolds and Morissette, whom we once referred to as Canada's First Couple.

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JANUARY & ASHTON

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Kutcher and Jones met in 1998 while modeling for Abercrombie and Fitch, which just proves how difficult it is to be good-looking … oh, wait. "[He] was not supportive of my acting," Jones later said of their three-year relationship. "If anything I should thank him. Because the minute you tell me I can't do something, that's when I'm most motivated."

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MILA & MACAULAY

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Meanwhile, Kutcher's wife had her own romance brewing: Kunis and Culkin dated for eight years before their 2011 split, a truly devastating blow for Home Alone fans who also watch Family Guy.

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TOM & SOFIA

Bauer-Griffin

No one remind Joe Manganiello that his wife was spotted out with Cruise in 2005, although Vergara later countered, "It's funny because the media creates what they want to create."

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Kate Hudson & Dax Shepard Dated, Plus 19 More Celeb Pairs You Totally Forgot About

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Kate & Dax

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Carrie & John

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Katy & Josh

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Nicole & Lenny

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Jenna & Justin

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Jessica & Chris

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Kirsten & Jake

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Winona & Matt

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Shia & Rihanna

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Sarah & Robert

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TOPHER & IVANKA

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GIGI & CODY

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BRITNEY & KEVIN

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NICK & KIM

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RYAN & SANDRA

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NICK & MILEY

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ALANIS & RYAN

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JANUARY & ASHTON

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MILA & MACAULAY

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TOM & SOFIA

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