They are no longer together, but their memories live on in our hearts (and on the Internet).
From: Harper’s BAZAAR US
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https://www.harpersbazaar.com.sg/gallery/celeb-couples-who-defined-the-2000s/
45 Celeb Couples You Were Obsessed With In The 2000s
PUFF DADDY AND JENNIFER LOPEZ
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45 Celeb Couples You Were Obsessed With In The 2000s
J.Lo and Puffy dated from 1999 to 2001 (when he was still known as Puff Daddy). Following their split, Puffy told The New York Daily News, "... I'm happy for her. I'll always be there for Jennifer, whether business or personal." Photo: Getty
CARSON DALY AND TARA REID
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45 Celeb Couples You Were Obsessed With In The 2000s
Carson and Tara began dating in 2000 after meeting on the set of TRL. They had a short-lived engagement before splitting altogether in the summer of 2001.Photo: Getty
KATIE HOLMES AND CHRIS KLEIN
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45 Celeb Couples You Were Obsessed With In The 2000s
Chris and Katie were together from 2000 to 2005 and were even engaged at one point. Katie would date Tom Cruise just a few months later. Photo: Getty
MISCHA BARTON AND BRANDON DAVIS
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45 Celeb Couples You Were Obsessed With In The 2000s
Photo: Getty
RYAN GOSLING AND SANDRA BULLOCK
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45 Celeb Couples You Were Obsessed With In The 2000s
Ryan and Sandy dated from 2002 to 2003 after meeting on the set of Murder by Numbers. He later told The Times that he "had two of the greatest girlfriends of all time," referring to Sandra and another ex, Rachel McAdams. Photo: Getty
JENNIFER LOPEZ AND BEN AFFLECK
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45 Celeb Couples You Were Obsessed With In The 2000s
"Bennifer" was born in 2002 shortly after the production of Gigli. Ben would go on to star in the "Jenny From the Block" music video, propose to J.Lo, and make Jersey Girl. More than 10 years after their split, J.Lo told People earlier this year that "there was a genuine love" there. Photo: Getty
JARED LETO & CAMERON DIAZ
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45 Celeb Couples You Were Obsessed With In The 2000s
Jared and Cameron's romance ended in 2003 following nearly four years of dating and a rumored engagement. Photo: Getty
NICK LACHEY & JESSICA SIMPSON
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45 Celeb Couples You Were Obsessed With In The 2000s
Nick and Jessica were on and off from 1998 to 2002, at which point they became engaged and married. Their marriage would last three years and bring you the greatest 60 seconds of television. Photo: Getty
JAKE GYLLENHAAL AND KIRSTEN DUNST
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45 Celeb Couples You Were Obsessed With In The 2000s
Jake and Kirsten dated for two years after meeting through his sister Maggie in 2002. At one point, they shared ownership of a dog named Atticus. Photo: Getty
ALANIS MORISSETTE AND RYAN REYNOLDS
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45 Celeb Couples You Were Obsessed With In The 2000s
Canada's first couple dated for two years before announcing their engagement in 2004. They broke up in 2007 and Alanis would go on to write about her heartbreak on Flavors of Entanglement. "It's really about my grief," she told Access Hollywood at the time. Photo: Getty
ADAM BRODY AND RACHEL BILSON
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45 Celeb Couples You Were Obsessed With In The 2000s
Seth and Summer dated IRL for three years before splitting up in 2006. No word on what happened to Penny Lane, the pit bull terrier they adopted together. Photo: Getty
JESSICA BIEL & CHRIS EVANS
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45 Celeb Couples You Were Obsessed With In The 2000s
Chris and Jessica dated from 2001 to 2006, shortly before he became Captain America and before she met Justin Timberlake. Photo: Getty
SCARLETT JOHANSSON AND JOSH HARTNETT
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45 Celeb Couples You Were Obsessed With In The 2000s
ScarJo and Josh dated after meeting on the set of Black Dahlia and split in 2006. Josh later reportedly said the breakup was "really painful." Photo: Getty
WILMER VALDERRAMA AND MANDY MOORE
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45 Celeb Couples You Were Obsessed With In The 2000s
Mandy and Wilmer dated from 2000 to 2002, which unfortunately gave Wilmer what he thought was a green light to reveal intimate details about their relationship. In 2006, while he told the New York Times Mandy was "the first love of my life," he also told Howard Stern about taking Mandy's virginity and how their sex was "really good." Photo: Getty
NICOLE RICHIE AND DJ AM
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45 Celeb Couples You Were Obsessed With In The 2000s
Nicole and AM had a tumultuous on-again-off-again relationship from 2004 to 2006 and even got engaged at one point. In a statement to People, they confirmed the split was amicable. (AM died of a drug overdose in 2009.) Photo: Getty
ASHLEE SIMPSON AND RYAN CABRERA
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45 Celeb Couples You Were Obsessed With In The 2000s
Ashlee and Ryan dated for about a year shortly after she starred in his debut music video for "On the Way Down" in 2004. Their love was briefly documented on her MTV series The Ashlee Simpson Show. Photo: Getty
WILMER VALDERRAMA AND LINDSAY LOHAN
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45 Celeb Couples You Were Obsessed With In The 2000s
Lindsay and Wilmer dated briefly in 2004, when That '70s Show was in its heyday. In 2014, Lindsay said that the song "Over," from her debut album Speak, was about their relationship. Photo: Getty
KATE BOSWORTH AND ORLANDO BLOOM
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45 Celeb Couples You Were Obsessed With In The 2000s
Kate and Orlando dated off and on from 2002 to 2006 after meeting during a shoot for a Gap ad. In 2011, Kate said that the breakup was so painful she felt like she had vertigo. Photo: Getty
KEVIN FEDERLINE AND BRITNEY SPEARS
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45 Celeb Couples You Were Obsessed With In The 2000s
K-Fed and Britney got engaged in July 2004 after only three months of dating, then tied the knot in September. Their torrid love affair was documented on the short-lived but legendary reality show Britney and Kevin: Chaotic. They had two children together, Sean and Jayden, before Britney filed for divorce in November 2006 citing "irreconcilable differences." Photo: Getty
ROSARIO DAWSON AND JASON LEWIS
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45 Celeb Couples You Were Obsessed With In The 2000s
Rosario and Jason started dating in 2004, just as Jason was coming off his run on Sex and the City as Samantha's extremely hot (and much younger) boyfriend. They split in 2006. Photo: Getty
TOM CRUISE AND SOFIA VERGARA
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45 Celeb Couples You Were Obsessed With In The 2000s
According to Andrew Morton's book Tom Cruise: An Unauthorized Biography, Tom dated Sofia after his 2004 split from Penelope Cruz but before his whirlwind romance with Katie Holmes in 2005. Morton claims Sofia ended it because she wasn't thrilled about Tom's devotion to Scientology. Photo: Getty
DITA VON TEESE AND MARILYN MANSON
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45 Celeb Couples You Were Obsessed With In The 2000s
Marilyn started dating Dita after he and Rose McGowan broke off their engagement in 2001. They were married in 2004, in a ceremony officiated by avant-garde director Alejandro Jodorowsky. Dita filed for divorce in 2006, after Marilyn began an affair with Evan Rachel Wood. Photo: Getty
PARIS LATSIS AND PARIS HILTON
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45 Celeb Couples You Were Obsessed With In The 2000s
Paris and Paris (Paris Squared, if you will) got engaged in 2005 after five months of dating. The couple name was perfect, but apparently the relationship was not — Paris H. broke it off four months later. Photo: Getty
KEIRA KNIGHTLEY AND JAMIE DORNAN
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45 Celeb Couples You Were Obsessed With In The 2000s
Before he was Christian Grey (or even The Golden Torso), Jamie dated Keira, who was also on her way up after a scene-stealing role in the first Pirates of the Caribbean movie. They broke up in 2005, but photos of Jamie's baggy jeans live on. Photo: Getty
JOEL MADDEN AND HILARY DUFF
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45 Celeb Couples You Were Obsessed With In The 2000s
They dated for 2.5 years, but only went public after she turned 18 (he was eight years her senior). "I had a 26-year-old boyfriend," Hilary said in an interview Cosmopolitan, when asked about losing her virginity. "So everyone can make their own assumptions about what I was doing." Photo: Getty
MACAULAY CULKIN AND MILA KUNIS
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45 Celeb Couples You Were Obsessed With In The 2000s
They dated for eight years before calling it quits in 2011. "We grew up together," she told Women's Health in 2009. "You find a steady rock in your life and that's all you need. We have our ups and downs, but work through them." Until you don't. Photo: Getty
BRODY JENNER AND KRISTIN CAVALLARI
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45 Celeb Couples You Were Obsessed With In The 2000s
Although Brody admitted last year that his relationship with Lauren Conrad was staged for the cameras, he did in fact date Kristin for about a year-and-a-half. They broke up in 2006. Photo: Getty
CLAIRE DANES AND BILLY CRUDUP
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45 Celeb Couples You Were Obsessed With In The 2000s
He left his girlfriend of eight years, Mary-Louise Parker, in 2003, while she was seven months pregnant, to be with his Stage Beauty co-star. They lasted four years. Photo: Getty
MANDY MOORE AND ZACH BRAFF
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45 Celeb Couples You Were Obsessed With In The 2000s
They dated for about two years, from late 2004 until October 2006 and both gave interviews shortly after their split about battling depression. Photo: Getty
RYAN GOSLING AND RACHEL MCADAMS
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45 Celeb Couples You Were Obsessed With In The 2000s
The Notebook co-stars dated for several years before breaking up in 2007. Ryan told GQ of their split: "The only thing I remember is we both went down swingin' and we called it a draw." Photo: Getty
KANYE WEST AND ALEXIS PHIFER
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45 Celeb Couples You Were Obsessed With In The 2000s
They dated on and off for six years and got engaged in 2006. By 2008, not long after his mother Donda's death, they broke up, ultimately giving us one of the greatest albums in music history: 808s and Heartbreak. Photo: Getty
MICHELLE WILLIAMS AND HEATH LEDGER
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45 Celeb Couples You Were Obsessed With In The 2000s
After three years and a child together, the Brokeback Mountain co-stars ended their relationship in September 2007. Ledger was found dead in his apartment in January 2008. "My heart is broken," Michelle said in a statement so sad it can still bring you to tears. Photo: Getty
PARIS HILTON AND STAVROS NIARCHOS
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45 Celeb Couples You Were Obsessed With In The 2000s
The Greek shipping heir broke up with Mary-Kate Olsen to be with his heiress in 2005, only to split from her a year later. Not one but two publicists gave statements on Paris's behalf to People. Photo: Getty
KANYE WEST AND AMBER ROSE
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45 Celeb Couples You Were Obsessed With In The 2000s
Kanye and Amber started dating not long after his split from Alexis Phifer. Their relationship reportedly inspired "The Blame Game," off My Beautiful Dark Twisted Fantasy. More than six years later, they can still make beautiful news together.Photo: Getty
EVAN RACHEL WOOD AND MARILYN MANSON
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45 Celeb Couples You Were Obsessed With In The 2000s
They got engaged in 2010, after dating on-and-off for four years (he proposed on stage in Paris). They broke up before ever tying the knot. Photo: Getty
BLAKE LIVELY AND PENN BADGLEY
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45 Celeb Couples You Were Obsessed With In The 2000s
Just like Serena van der Woodsen and Dan Humphrey, the Gossip Girl co-stars didn't last. They became exes (xoxo) in 2010. Photo: Getty
KIM KARDASHIAN AND NICK CANNON
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45 Celeb Couples You Were Obsessed With In The 2000s
How could you forget they were a thing for a hot second in 2006? Nick won't let you! Photo: Getty
MARIAH CAREY AND NICK CANNON
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45 Celeb Couples You Were Obsessed With In The 2000s
In April 2008, her rep denied she and Nick were dating. A month later, she was his wife. They split last year and Nick has said he'll probably never marry again. Photo: Getty
JAKE GYLLENHAAL AND REESE WITHERSPOON
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45 Celeb Couples You Were Obsessed With In The 2000s
They started dating in 2007, not long after Reese's divorce from Ryan Phillippe and lasted three years. This year, he called her "one of the smartest, strongest people [he's] ever met." Photo: Getty
They started dating in 2007, not long after Reese's divorce from Ryan Phillippe and lasted three years. This year, he called her "one of the smartest, strongest people [he's] ever met."
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45 Celeb Couples You Were Obsessed With In The 2000s
"I ended a relationship to be alone because I don't want to waste somebody's time if something's not right," John told reporters outside his gym, after he and Jen split for the first time in 2008. They got back together and split again the following year. Good riddance, buddy. Photo: Getty
"I ended a relationship to be alone because I don't want to waste somebody's time if something's not right," John told reporters outside his gym, after he and Jen split for the first time in 2008. They got back together and split again the following year. Good riddance, buddy.
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45 Celeb Couples You Were Obsessed With In The 2000s
They ended their three-year relationship in 2006, and in 2011, starred in Bad Teacher together, proving their was no bad blood.
Photo: Getty
They ended their three-year relationship in 2006, and in 2011, starred in Bad Teacher together, proving their was no bad blood.
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45 Celeb Couples You Were Obsessed With In The 2000s
The One Tree Hill co-stars began dating in 2003 and wed in 2005. Five months later, they were separated. "This is a difficult and unfortunate situation," Sophia said in a statement. "I am glad this is being resolved sooner rather than later." Chilling. Photo: Getty
KELIS AND NAS
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45 Celeb Couples You Were Obsessed With In The 2000s
The love story of Kelis and Nas ended in 2009 after nearly seven years together (four of which they were married). Kelis filed for divorce when she was seven months pregnant with their first child, Knight.Photo: Getty
AARON CARTER AND HILARY DUFF
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45 Celeb Couples You Were Obsessed With In The 2000s
Remember when Aaron and Hilary dated at the same time he dated LiLo (2000 to 2003)? Remember when Aaron couldn't stop talking about his love for Hil years later and she was like, "Boy, bye?" Photo: Getty
JOHN MAYER AND JESSICA SIMPSON
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45 Celeb Couples You Were Obsessed With In The 2000s
She was his "sexual napalm" from 2006 to 2007. Photo: Getty
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