The early 2000s seem like a lifetime ago. It was a simpler time, when Justin Timberlake and Britney Spears wore matching denim outifts, low-rise jeans were super trendy and COVID-19 had never been heard of.
While these couples didn’t last, they have become iconic pairings in celebrity history. Here are a few of our favourite celebrity couples from the early 2000s that have since gone their separate ways.
Jake Gyllenhaal and Reese Witherspoon
The actors met on the set of the 2007 political thriller film Rendition and dated from 2007 to 2009.
Mila Kunis and Macauley Culkin
Before marrying Ashton Kutcher, Mila Kunis dated Home Alone star Macauley Culkin for eight years from 2002 to 2011.
J.Lo and P.Diddy
Back when he was still Puff Daddy, the iconic rapper and Jenny from the Block were an item. They dated from 1999 to 2001, and split because of Diddy’s infidelity. Diddy has since called her one of his greatest loves.
Cameron Diaz and Justin Timberlake
The pair met at the Nickelodeon Kids’ Choice Awards in 2003 to dated until 2007. Their split is said to be mutual.
Britney Spears and Justin Timberlake
There is no other 2000s couple more iconic than Britney Spears and Justin Timberlake. The pair began dating in 1999 and gave us cute moments like their matching denim moment, before splitting in 2002. Timberlake’s song ‘Cry Me a River’ was released soon after their break up, and is believed to be about Spears.
Ashanti and Nelly
The iconic RnB performers dated for a whole decade before breaking up in 2013. While she didn’t elaborate on reasons why, Ashanti did say in an interview that she had been betrayed.
Michael Bublé and Emily Blunt
Everyone’s favourite Christmas-time singer dated Devil Wears Prada actress Emily Blunt from 2005 to 2008. Blunt has since gone on to marry John Krasinksi and Bublé married Argentinian actress Luisana Lopilato.
Michael Cera and Aubrey Plaza
Comedy actors Michael Cera and Aubrey Plaza were an item for a year-and-a-half after meeting on the set of Scott Pilgrim Vs. The World in 2009, and almost eloped together in Las Vegas. They remain good friends.
Ciara and Bow Wow
Before she married Russell Wilson, Ciara was engaged to rapper and actor Bow Wow back in 2006. The pair dated for two years.
Matthew McConaughey and Janet Jackson
This incredibly unlikely pair briefly dated in 2002. Jackson confirmed the short-lived romance in 2006, saying it was ‘just for a minute’.
Tom Cruise and Penélope Cruz
The actors met on the set of their 2001 film Vanilla Sky and continued to date for three years.
Jennifer Aniston and Brad Pitt
Jennifer Aniston and Brad Pitt were once one of the most famous celebrity couples. They began dating in 1998, married in 2000 and divorced in 2005. Pitt later married Mrs and Mrs Smith co-star Angelina Jolie, who went on to say they fell in love while filming the movie in 2004 (while Pitt was still married to Aniston).
Feature image: Pinterest
