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2000s Celebrity Couples You Likely Forgot Were Once A Thing

Apr 17, 2026
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Rewind to the early 2000s, and Hollywood looked very different, especially when it came to celebrity dating. While some headline-making romances are still fresh in our memories, plenty of unexpected pairings have quietly faded from pop culture history. Take Jessica Biel and Chris Evans, who met early in their careers and dated from 2001 to 2006, long before Evans became a Marvel superstar. The pair even co-starred in two films together: ‘Cellular’ in 2004 and ‘London’ in 2005. Around that same time, Justin Timberlake and Cameron Diaz were linked after reportedly meeting at the 2003 Kids’ Choice Awards, where he picked up the award for “Best Burp”, not exactly your typical love story, especially since Diaz presented it. Meanwhile, ‘Bridget Jones’ actress Renée Zellweger and singer Kenny Chesney had a whirlwind marriage in 2005 that ended after just four months, with Zellweger filing for an annulment and citing “fraud” as the reason for the split.
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