The early ’00s were a crazy time to be alive . It was a generational segue from analog into the digital age — an era ripe with promise, that boasted seemingly endless possibilities.
It was also an absolute gong show when it came to the world of celebrity dating . So, in case you might’ve forgotten (or maybe you hadn’t even been born yet), here are some very random celebrity couples who dated in the ’00s .
Mandy Moore and Zach Braff
Mandy and Zach began dating in 2004. The couple was so in love with one another that Mandy even had a cameo appearance in Scrubs . Sadly, the two decided to call off their romance later that same year.
Penélope Cruz and Matthew McConaughey
Many people have likely long forgotten the ill-fated adventure comedy, Sahara — the birthplace of Matthew and Penélope Cruz’s relationship . While these two were certainly a feast for the eyes, their relationship lasted only a little longer than Sahara ‘s theater stay.
Matt Damon and Winona Ryder
I bet you’d completely forgotten that Winona and Matt were once the talks of the town. The pair were rumored to have gotten together while Matt was still dating his Good Will Hunting co-star, Minnie Driver.
Britney Spears and Colin Farrell
Fresh from her breakup with Justin Timberlake, Britney had a desire to dip her toes into the bad boy pond , and in the early ’00s — bad boys didn’t come much better than Colin Farrell.
Carson Daly and Tara Reid
The only thing that makes this photo even more ’00s than it already appears to be, is the fact that Carson and Tara took this snapshot while they were attending Joe’s album release party .
Nicole Kidman and Lenny Kravitz
That’s right, Nicole and Lenny were once a couple! Things got even more meta years later when Lenny’s daughter, Zoë Kravitz, was cast to appear in HBO’s Big Little Lies , opposite her dad’s former flame.
Alanis Morissette and Ryan Reynolds
Ryan and Alanis were practically Canadian royalty, but sadly their love wasn’t meant to last. They dated for a little more than four years before calling it quits in 2007. It’s a little bit “Ironic,” don’t you think?
Fred Durst and Carmen Electra
If you still don’t believe that the early ’00s was a real-life Twilight Zone , hearing that Limp Bizkit was arguably the most popular band on the planet ought to set you straight. How Fred Durst ever managed to land a woman like Carmen Electra still defies all logic and rationale.
Ryan Reynolds and Kristen Johnston
Ryan Reynolds was a busy man in the late ’90s and into the early ’00s. In case you’ve forgotten who Kristen Johnston is, she’s best known for her work on 3rd Rock from the Sun and Austin Powers: The Spy Who Shagged Me.
LeAnn Rimes and Andrew Keegan
Long before LeAnn began her illicit affair with her now-husband, Eddie Cibrian, she was involved with ’90s heartthrob, Andrew Keegan . If you’re wondering where you recognize Andrew from, he had memorable roles in films like Camp Nowhere and 10 Things I Hate About You.
Ashton Kutcher and January Jones
Ashton and January dated from 1998 until early 2001. According to a GQ interview given by Jones, Ashton reportedly wasn’t the biggest supporter of her acting career and went as far as to advise against her getting into the business.
John Mayer and Jessica Simpson
John Mayer’s list of A-list conquests is as long as my arm, and it includes everyone from Katy Perry to Jessica Simpson. In a now-infamous interview with Playboy , Mayer said “The girl is like crack cocaine to me. Sexually, it was crazy. That’s all I’ll say. It was like napalm, sexual napalm .”
Katie Holmes and Chris Klein
Katie Holmes was the girl next door from Dawson’s Creek and Klein was the proverbial heartthrob of American Pie . Two months after these two split, Katie announced that she had begun dating Tom Cruise .
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Kirsten Dunst and Jake Gyllenhaal
The multiverse really is a strange and magnificent place. How else could you begin to explain how Mary-Jane Watson and Spider-Man’s nemesis, Mysterio , were able to make it work for as long as they did?
Deryck Whibley and Paris Hilton
Deryk and Paris began dating in the “Summer” of 2003 . Clearly, the pop-punk star got “In Too Deep” as they had parted ways just five short months after their relationship began. When Deryk was asked why the relationship didn’t work, he said it was “Over My Head.”
