7 Celebrity Couples Who Defined the Early Aughts with Their Romances
7 Celebrity Couples Who Defined the Early Aughts with Their Romances
Nicole BrieseWed, June 24, 2026 at 10:00 AM UTC
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Britney Spears and Justin Timberlake on September 7th, 2000 in New York; Brad Pitt and Jennifer Aniston on May 10, 2004 in New York.Credit: Dave Hogan/Getty; Kevin Mazur/WireImage
The early aughts were a simpler time, particularly when it came to love.
Without celebrity dating apps like Raya, many of the era’s biggest romances, including Ben Affleck and Jennifer Lopez, Ryan Gosling and Rachel McAdams and Ashton Kutcher and Brittany Murphy blossomed after time spent together on set.
With the couples’ love stories playing out on-screen (or in song, in the case of both Justin Timberlake and Britney Spears and Nick Lachey and Jessica Simpson), fans were obsessed.
“We didn’t try to have a public relationship,” Lopez told PEOPLE of her relationship with Affleck in 2016. “We just happened to be together at the birth of the tabloids, and it was like ‘Oh my God.’ It was just a lot of pressure.”
The biggest headlinemakers have since split, but their short-lived romances live on in film and music.
"I wrote 'Cry Me a River' in two hours,” Timberlake once said of the hit track that was inspired by his and Spears’ breakup. “I didn't plan on writing it. The feelings I had were so strong that I had to write it, and I translated my feelings into a form where people could listen and, hopefully, relate to it."
From early infatuations to rekindled romances, revisit seven former couples we couldn't stop talking about in the 2000s below.
01 of 07
Nick Lachey and Jessica Simpson (1999 to 2005)
Jessica Simpson and Nick Lachey.Credit: Bob Riha Jr/WireImage
Newlyweds stars Jessica Simpson and Nick Lachey, who began dating in 1999 and wed in 2002, were named PEOPLE’s “most beautiful couple” in April 2005.
"After we met, I found myself looking through the crowds for her all night," Lachey told PEOPLE two years prior.
The singers, who were frequently apart for work, relied on trust, e-mail and video conferencing to keep their relationship strong. In the end, however, it wasn’t enough: The couple split in 2005 and finalized their divorce in 2006.
"We meant a lot to each other and we always will," Simpson told PEOPLE in 2020. "I want to be very respectful because I married him for a reason and we were together for seven years for a reason. He has a family now and I would never say anything to disrespect that."
02 of 07
Britney Spears and Justin Timberlake (1999 to 2002)
Britney Spears and Justin Timberlake.Credit: Jeffrey Mayer/WireImage
After two years of dating, Britney Spears believed she and Justin Timberlake would tie the knot. The pop star revealed as much in an interview with Britain’s ITV music show CD:UK: “It will happen some time in the future, but not this year,” she said in 2002.
Timberlake previously gushed over his then-girlfriend, telling Rolling Stone in 2001, “So many girls you meet in this business are so into themselves, and Britney is not. She’s as down-home as she was before she got into this. That’s the best thing about her. I got the cream of the crop. ... She makes me happy.”
The pair even toyed around with the idea of a potential collaboration. “It definitely would be a spectacle. It would be huge,” he said.
Neither the wedding nor the music panned out: Timberlake, who split from Spears in 2002, is now married to Jessica Biel. The pair have two children. Spears, for her part, also shares two kids with her ex-husband Kevin Federline.
03 of 07
Brad Pitt and Jennifer Aniston (1998 to 2005)
Jennifer Aniston and Brad Pitt attend the Palisades Pictures screening of "Going Upriver: The Long War of John Kerry" on Oct. 19, 2004 in Los Angeles, California.Credit: Jeff Vespa/WireImage
Brad Pitt promised to “pay the difference on the thermostat” during his 1998 wedding vows to Jennifer Aniston, who pledged to always make his “favorite banana milk shake.”
The Friends star was introspective when asked about their love in 2003. "Is he the love of my life? I think you're always sort of wondering ...” she told W. “I mean, I don't know. ... He's certainly a big love in my life ... And I know that we have something special, especially in all this chaos.”
Aniston, who has since called their marriage a “successful” one, was equally as vulnerable after their 2005 divorce, telling Vanity Fair, "I will love [Brad] for the rest of my life. He's a fantastic man. I don't regret any of it.”
Pitt said in a statement: “Jen is an incredibly giving, loving and hilarious woman who remains my friend. It is an important relationship I value greatly.”
The Just Go With It star has been with boyfriend Jim Curtis since July 2025; Pitt is currently dating Ines de Ramon.
04 of 07
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Ryan Gosling and Rachel McAdams (2005 to 2007)
Ryan Gosling and Rachel McAdams.Credit: Gregg DeGuire/WireImage
Ryan Gosling looked back on his two-year relationship with his The Notebook costar Rachel McAdams fondly, even after their 2007 split.
“God bless The Notebook,” the former Mickey Mouse Club actor told GQ. “It introduced me to one of the great loves of my life. But people do Rachel and me a disservice by assuming we were anything like the people in that movie. Rachel and my love story is a hell of a lot more romantic than that.”
Though they gave it their all (“We both went down swingin’ and we called it a draw,” said Gosling), and shared one very memorable MTV Kiss, they ultimately went their separate ways in 2007.
Gosling subsequently coupled up with his now-wife Eva Mendes, with whom he shares two children. McAdams moved on with Jamie Linden, with whom she also has two kids.
05 of 07
Ryan Phillippe and Reese Witherspoon (1997 to 2006)
Reese Witherspoon and Ryan Phillippe attend the premiere of "Gosford Park" on December 3, 2001 in New York City.Credit: George De Sota/Getty
Sparks flew on Reese Witherspoon’s 21st birthday in 1997 after a friend brought Ryan Phillippe to her party.
"I think you're my present," Witherspoon recalled saying to her future husband, whom she married in 1999.
Despite their combined star power, Witherspoon said she was “not interested in the fallacy of the Hollywood relationship,” adding, “We’re normal people with normal problems.”
According to Phillippe, their young age ultimately drove the Cruel Intentions costars apart and they split in 2006. "When we got together we were so young," he told Larry King. "I think it can create issues with two people in this industry because there's so much noise that goes along with it."
The former couple share daughter Ava and son Deacon. Phillippe is also a dad to son Kai with his ex-girlfriend Alexis Knapp, while Witherspoon shares son Tennessee with ex-husband Jim Toth.
06 of 07
Brittany Murphy and Ashton Kutcher (2002 to 2003)
Ashton Kutcher and Brittany Murphy during VH1 Big in 2002 Awards in Los Angeles, California.Credit: KMazur/WireImage
Ashton Kutcher and Brittany Murphy’s on-screen love affair in Just Married ultimately transitioned into a real-life (albeit short-lived) relationship.
“When we were doing the movie, we were just friends," the That '70s Show alum told PEOPLE of Murphy. "We just kind of started hanging out more. And now we've been hanging out a lot more."
The duo sparked wedding buzz after buying each other wedding bands as a wrap present for the film, however, they broke up shortly after the movie premiered in January 2003. “We’re just kind of companions, we just like spending a lot of time together,” Kutcher told the .
Kutcher, who married fellow That ‘70s Show star Mila Kunis in 2015, wrote that the “world lost a little piece of sunshine” following Murphy’s 2009 death from pneumonia.
07 of 07
Ben Affleck and Jennifer Lopez (2002 to 2004)
Jennifer Lopez and Ben Affleck.Credit: Tom Kingston/WireImage
Affleck and Lopez had previously met in passing at parties, per Lopez, but “got along great” right from the get-go after they starred opposite each other in the 2003 rom-com Gigli.
“I felt like … ‘Okay, this is it,' ” Lopez told PEOPLE about connecting with her future husband.
The couple, who got engaged in 2002, began as “really good friends,” finding a lot of common ground through their shared experiences. “We're probably more alike and from the same kind of background,” Lopez once explained in an interview with Diane Sawyer. “Same kind of upbringing and same kind of family and same kind of house."
Though they called things off in 2004, they rekindled their romance nearly 20 years later, tying the knot in a “super small” ceremony in 2022.
"I feel so lucky and happy and proud to be with him," Lopez told PEOPLE. "It's a beautiful love story that we got a second chance."
Two years later, however, the Unstoppable actress filed for divorce. Their split was finalized on Jan. 6, 2025.
“There is no, 'This is what happened,' " Affleck told GQ that March. "It’s just a story about people trying to figure out their lives and relationships in ways that we all sort of normally do."
on People
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