14 Weird Celeb Coupled That Dated in the 2000s

The 2000’s might have been an era of FRIENDS, Harry Potter, Clinton, and Bush, but it was also the age of mismatched couples in Hollywood.

Although these couples didn’t seem weird back then, the images in this article will have you guffawing with What? and Whys? Read on to know more.

Movie And Songs

After meeting at an award show in 2002, Matthew McConaughey and Janet Jackson were dating for some time during that period.



Cyclist Meets Beauty

Ashley Olsen dated Lance Armstrong in 2007. They had a 15-year age gap between them.


Punking It

2004 to 2006 saw Hillary Duff,16  dating Joel Madden, 25.



Misson Failed

Then there was Tom Cruise almost dating Sofia Vergara in 2005.


The Singing Duo

The heartbreaking song of Taylor Swift’s “Dear John” was inspired by John Mayer, whom she was dating in 2009- 2010.


Laughing Matter

Drew Barrymore was married from July to December in 2001, to comedian Tom Green.

That’s So 70’s

When Lindsay Lohan dated Wilmer Valderrama back in 2004, she went on to make a special appearance in the sitcom which he starred in, That ’70s Show.


Cradling Snatching

Sandra Bullock, 37 dated Ryan Gosling, 21 from 2002-2003. I am guessing you didn’t know this.

Unlock It

Matt Damon and Winona Ryde did not shy away, from flaunting their relationship from 2001- 2003.


Goth Beauty

Evan Rachel Wood and Marilyn Manson started dating in 2007. They were even engaged for some time, but finally called quits in 2010.


Rebound Take

After his breakup with Courtney Love, Edward Norton dated Salma Hayek for almost four years.


Before Kimye

Kim Kardashian dated Nick Lachey for a short period, before becoming Mrs.Kayne West.


Transforming Relationship

Although friends now, Rihanna and Shia LaBeouf dated back in 2007.



Engagement Invite

Around 1999, Jared Leto and Cameron Diaz started dating. They even got engaged but, called off their relationship in 2003.



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