Celebrity Couples You Totally Forgot About

We're taking a romantic stroll down memory lane with Nicole Kidman and Lenny Kravitz, Jenna Dewan and Justin Timberlake and more throwback couples

01 of 22

Melissa Joan Hart & Ryan Reynolds

SABRINA, THE TEENAGE WITCH, Melissa Joan Hart, Ryan Reynolds, 1996. Showtime Network / Courtesy: Everett Collection Copyright
Melissa Joan Hart and Ryan Reynolds. Everett

Speaking on the Hey Dude…The 90s Called! podcast in February 2023, Hart spoke about a "little thing" she shared with Ryan Reynolds when they worked on the 1996 movie Sabrina the Teenage Witch (which preceded Hart's hit show of the same name). The film featured Reynolds in the role of Seth, Sabrina's love interest.

Hart previously opened up about her romantic history with the Deadpool star in 2017 on Australian talk show Studio 10. "He was adorable. He was a really nice guy," she explained, adding that Reynolds was quite different from the famed heartthrob he is today: "You can see in the clip the crazy hair. He was sweet — he was very sweet."

As "smitten and cute" as Hart says they were, she says they were ultimately not meant to be. "I had a boyfriend at the time," the actress said during her Studio 10 appearance. "[Reynolds] probably would have been a great boyfriend. And I didn't end up with the other guy, so maybe I should have taken a chance!"

02 of 22

Matthew Perry & Julia Roberts

FRIENDS Actor Matthew Perry and actress Julia Roberts
Matthew Perry and Julia Roberts. Getty Images / Stringer

While shooting Friends, on which Roberts famously guested in 1996, Perry found himself dating the megastar, and wrote about their time brief together in his 2022 memoir.

"Two months later, I was single," he recalled. "Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unloveable."

He continued: "So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts. She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her. I can't begin to describe the look of confusion on her face."

03 of 22

Luke Wilson & Drew Barrymore

Luke Wilson and Drew Barrymore
Luke Wilson and Drew Barrymore in 1999. Ron Galella, Ltd./Getty Images

In a January 2022 with Kate Hudson, Barrymore remembered a time when she was dating Luke Wilson ... who was also dating other people.

"It was an open relationship; we were young," she added.

"I've been there with a Wilson too," said Hudson with a laugh. (Hudson previously dated Luke's older brother Owen Wilson off and on, after the two filmed 2006's You, Me and Dupree together.)

For Barrymore, that time in her life is something she looks back on with fond memories, as she realizes it was "low stakes."

"We're just young, we're having fun, we're all playing, acting, hanging out. You're not taking it all so seriously, and it was fun and we had the best time," she said.

04 of 22

Audrina Patridge & Chris Pine

Audrina Patridge, Chris Pine
Audrina Patridge, Chris Pine. Craig Barritt/Getty; Frazer Harrison/Getty

During an appearance on the Hollywood Raw podcast, co-host Adam Glyn asked the Hills: New Beginnings star about the "biggest celebrity" she's ever dated that nobody knows about.

"This is whenever his movie just came out and I had just finished [my 2009 movie] Sorority Row. So we were all in Vegas for an award show, Rumer Willis and the whole cast [of Sorority Row]. [Chris Pine] came up to me and introduced himself to me and gave me his number," the reality star recalled.

"And all the girls were kicking me under the table like, 'Oh, my God. You don't know who that is?' I'm like, 'No.' They're like, 'That's Chris Pine.' I was like, 'Oh, he's hot,'" she said.

Patridge, who previously sparked dating rumors with Pine in the early aughts, said that they "went out more than a few times." During that time, she was filming the original Hills series as he was on the rise as a high-profile movie star.

"He didn't like the whole paparazzi side of it. That was my life, was going out and I was followed by paparazzi. So being on The Hills, our lives completely opposite and just so different with my lifestyle and filming," she continued. "He was more a real actor, theater actor and loved to read books and jazz music and didn't really like to go out to clubs or anything like that."

Patridge said that Pine was a "nice guy" and a "gentleman," but said that "it just kind of dissipated" between them in the end.

05 of 22

Kate Hudson & Dax Shepard

kate hudson, dax shepherd
Frazer Harrison/Getty Images; Taylor Hill/FilmMagic

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 engaged to Danny Fujikawa, and the pair welcomed their first child — and Hudson's first daughter — Rani Rose in October 2018.

06 of 22

Carrie Ann Inaba & John Stamos

Kelsey McNeal/ABC via Getty

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.'

07 of 22

Katy Perry & Josh Groban

Allen Berezovsky/Getty; Bryan Bedder/Getty

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."

08 of 22

Nicole Kidman & Lenny Kravitz

2013 CMT Music Awards - Red Carpet
Kevin Mazur/WireImage

Kidman 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.

09 of 22

Jenna Dewan & Justin Timberlake

44th Annual Grammy Awards - Show
Frank Micelotta/ImageDirect

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.

10 of 22

Jessica Biel & Chris Evans

jessica biel and chris evans
Jon Kopaloff/FilmMagic

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.

11 of 22

Kirsten Dunst & Jake Gyllenhaal

2003 MTV Movie Awards - Backstage and Audience
Jeff Vespa/WireImage

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.

12 of 22

Winona Ryder & Matt Damon

Gilbert Flores/Celebrity Photo

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.

13 of 22

Sarah Jessica Parker & Robert Downey Jr.

61st Annual Academy Awards - Arrivals
Barry King/WireImage

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."

14 of 22

Topher Grace & Ivanka Trump

Kevin Winter/Getty; Ida Mae Astute/ABC via Getty

BlacKkKlansman actor Topher Grace relived memories of his early 2000s relationship with 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."

15 of 22

Gigi Hadid & Cody Simpson

David Livingston/Getty

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.

16 of 22

Nick Lachey & Kim Kardashian

Joey Foley/WireImage

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

17 of 22

Ryan Gosling & Sandra Bullock

Francois Guillot/Getty

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.

18 of 22

Nick Jonas & Miley Cyrus

Mathew Imaging/FilmMagic

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.

19 of 22

Alanis Morissette & Ryan Reynolds


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.

20 of 22

January Jones & Ashton Kutcher

Richard Corkery/NY Daily News Archive/Getty

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."

21 of 22

Mila Kunis & Macaulay Culkin

Dimitrios Kambouris/WireImage

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.

22 of 22

Tom Cruise & Sofia Vergara


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."

Related Articles