01of 22Melissa Joan Hart & Ryan ReynoldsMelissa Joan Hart and Ryan Reynolds.EverettSpeaking on theHey Dude…The 90s Called!podcast in February 2023,Hartspoke about a “little thing"she shared with Ryan Reynoldswhen they worked on the 1996 movieSabrina 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 romantichistory with theDeadpoolstarin 2017 on Australian talk showStudio 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 herStudio 10appearance. “[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!”
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Melissa Joan Hart & Ryan Reynolds
Melissa Joan Hart and Ryan Reynolds.Everett
Speaking on theHey Dude…The 90s Called!podcast in February 2023,Hartspoke about a “little thing"she shared with Ryan Reynoldswhen they worked on the 1996 movieSabrina 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 romantichistory with theDeadpoolstarin 2017 on Australian talk showStudio 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 herStudio 10appearance. “[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!”
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Matthew Perry & Julia Roberts
Matthew Perry and Julia Roberts.Getty Images / Stringer
While shootingFriends,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. “DatingJulia Robertshad 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.”
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Luke Wilson & Drew Barrymore
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,” sheadded.
“I’ve been there with a Wilson too,” said Hudson with a laugh. (Hudson previously dated Luke’s older brotherOwen Wilsonoff and on, after the two filmed 2006’sYou, Me and Dupreetogether.)
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.
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Audrina Patridge & Chris Pine
Audrina Patridge, Chris Pine.Craig Barritt/Getty; Frazer Harrison/Getty
During an appearance on theHollywood Rawpodcast, co-host Adam Glyn asked theHills: New Beginningsstar 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 Willisand the whole cast [ofSorority 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’sChris Pine.’ I was like, ‘Oh, he’s hot,'” she said.
Patridge, who previouslysparked dating rumorswith Pine in the early aughts, said that they “went out more than a few times.” During that time, she was filming the originalHillsseries as he was on the rise as a high-profile movie star.
Patridge said that Pine was a “nice guy” and a “gentleman,” but said that “it just kind of dissipated” between them in the end.
05of 22Kate Hudson & Dax ShepardFrazer Harrison/Getty Images; Taylor Hill/FilmMagicThe former flames discussed their2007 whirlwind romanceand why it fizzled out during an episode ofArmchair 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-wifeKristen Bell. The couplegot married in 2013and currently share two daughters,DeltaandLincoln.Hudson is currently engaged toDanny Fujikawa, and the pair welcomed their first child — and Hudson’s first daughter —Rani Rosein October 2018.
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Kate Hudson & Dax Shepard
Frazer Harrison/Getty Images; Taylor Hill/FilmMagic
The former flames discussed their2007 whirlwind romanceand why it fizzled out during an episode ofArmchair 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-wifeKristen Bell. The couplegot married in 2013and currently share two daughters,DeltaandLincoln.
Hudson is currently engaged toDanny Fujikawa, and the pair welcomed their first child — and Hudson’s first daughter —Rani Rosein October 2018.
06of 22Carrie Ann Inaba & John StamosKelsey McNeal/ABC via GettyDancing with the StarsjudgeInaba sat down onThe Talk, revealing that she and theFull Housestarpreviously 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 toDancing with the Starsand 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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Carrie Ann Inaba & John Stamos
Kelsey McNeal/ABC via Getty
Dancing with the StarsjudgeInaba sat down onThe Talk, revealing that she and theFull Housestarpreviously 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 toDancing with the Starsand 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.’
07of 22Katy Perry & Josh GrobanAllen Berezovsky/Getty; Bryan Bedder/GettyDuring a chat on a September 2018 episode ofWatch What Happens Live,Groban revealedthat 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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Katy Perry & Josh Groban
Allen Berezovsky/Getty; Bryan Bedder/Getty
During a chat on a September 2018 episode ofWatch What Happens Live,Groban revealedthat 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.”
08of 22Nicole Kidman & Lenny KravitzKevin Mazur/WireImageKidman revealed that she wasonce engagedto the rocker, whom she dated in 2003. “It just wasn’t right,” she toldVanity Fairin 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 miniseriesBig Little Lies.“Well, I knew Zoë because I was engaged to her father. It’s all in the family,” she toldThe EDIT, adding, “I love Lenny; he’s a great guy.” The one-time lovebirds reunited backstage at the 2016 CMT Music Awards, where theyposed for sweet picturesalongside Kidman’s husband Keith Urban.
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Nicole Kidman & Lenny Kravitz
Kevin Mazur/WireImage
Kidman revealed that she wasonce engagedto the rocker, whom she dated in 2003. “It just wasn’t right,” she toldVanity Fairin 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 miniseriesBig Little Lies.“Well, I knew Zoë because I was engaged to her father. It’s all in the family,” she toldThe EDIT, adding, “I love Lenny; he’s a great guy.” The one-time lovebirds reunited backstage at the 2016 CMT Music Awards, where theyposed for sweet picturesalongside Kidman’s husband Keith Urban.
09of 22Jenna Dewan & Justin TimberlakeFrank Micelotta/ImageDirectThe 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 [withBritney Spears] — like during, after the breakup,” Dewanexplained onWatch 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 wasnotTimberlake’s “rebound chick” after he ended things with the princess of pop.
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Jenna Dewan & Justin Timberlake
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 [withBritney Spears] — like during, after the breakup,” Dewanexplained onWatch 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 wasnotTimberlake’s “rebound chick” after he ended things with the princess of pop.
10of 22Jessica Biel & Chris EvansJon Kopaloff/FilmMagicBefore she was truly in sync withJustin 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’sCellularand 2005’sLondon.
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Jessica Biel & Chris Evans
Jon Kopaloff/FilmMagic
Before she was truly in sync withJustin 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’sCellularand 2005’sLondon.
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Kirsten Dunst & Jake Gyllenhaal
Jeff Vespa/WireImage
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Winona Ryder & Matt Damon
Gilbert Flores/Celebrity Photo
13of 22Sarah Jessica Parker & Robert Downey Jr.Barry King/WireImageParker and Downey Jr. dated for seven years after meeting on their 1984 filmFirstborn.The relationship had a lasting effect on the actress, who in 2016told 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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Sarah Jessica Parker & Robert Downey Jr.
Barry King/WireImage
Parker and Downey Jr. dated for seven years after meeting on their 1984 filmFirstborn.The relationship had a lasting effect on the actress, who in 2016told 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.”
14of 22Topher Grace & Ivanka TrumpKevin Winter/Getty; Ida Mae Astute/ABC via GettyBlacKkKlansmanactor Topher Grace relived memories of his early 2000s relationship withDonald 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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Topher Grace & Ivanka Trump
Kevin Winter/Getty; Ida Mae Astute/ABC via Getty
BlacKkKlansmanactor Topher Grace relived memories of his early 2000s relationship withDonald 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.”
15of 22Gigi Hadid & Cody SimpsonDavid Livingston/GettyBefore 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 pairsplitin 2015.
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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 pairsplitin 2015.
16of 22Nick Lachey & Kim KardashianJoey Foley/WireImageYes, they were only briefly linked in 2006 (“We went to a movie,“Lacheywould 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.
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Nick Lachey & Kim Kardashian
Joey Foley/WireImage
Yes, they were only briefly linked in 2006 (“We went to a movie,“Lacheywould 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.
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Ryan Gosling & Sandra Bullock
Francois Guillot/Getty
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Nick Jonas & Miley Cyrus
Mathew Imaging/FilmMagic
19of 22Alanis Morissette & Ryan ReynoldsSGranitz/WireImageDearDrew Barrymore, thank you for uniting these lovebirds at your birthday party in 2002. Although they would go on tocall off their engagementin 2007, we’ll always cherish the time we shared withReynoldsand Morissette, whom we once referred to as Canada’s First Couple.
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Alanis Morissette & Ryan Reynolds
SGranitz/WireImage
DearDrew Barrymore, thank you for uniting these lovebirds at your birthday party in 2002. Although they would go on tocall off their engagementin 2007, we’ll always cherish the time we shared withReynoldsand Morissette, whom we once referred to as Canada’s First Couple.
20of 22January Jones & Ashton KutcherRichard Corkery/NY Daily News Archive/GettyKutcherandJonesmet 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 saidof 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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January Jones & Ashton Kutcher
Richard Corkery/NY Daily News Archive/Getty
KutcherandJonesmet 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 saidof 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.”
21of 22Mila Kunis & Macaulay CulkinDimitrios Kambouris/WireImageMeanwhile, Kutcher’s wife had her own romance brewing:Kunisand Culkin dated for eight years beforetheir 2011 split, a truly devastating blow forHome Alonefans who also watchFamily Guy.
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Mila Kunis & Macaulay Culkin
Dimitrios Kambouris/WireImage
Meanwhile, Kutcher’s wife had her own romance brewing:Kunisand Culkin dated for eight years beforetheir 2011 split, a truly devastating blow forHome Alonefans who also watchFamily Guy.
22of 22Tom Cruise & Sofia VergaraBauer-GriffinNo one remind Joe Manganiello that his wife was spotted out withCruisein 2005, althoughVergaralater countered, “It’s funny because the media creates what they want to create.”
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Tom Cruise & Sofia Vergara
Bauer-Griffin
No one remind Joe Manganiello that his wife was spotted out withCruisein 2005, althoughVergaralater countered, “It’s funny because the media creates what they want to create.”
source: people.com
