13 Weirdest Celebrity Couples Who Dated In The 2000s.

May 15th, 2020
Name Team

Relationships can be tough, and when they break, it can upset both the partners. Now, romance is the driving force of relationships, and it is capable making people do weird stuff, even celebrities. Some stars have done some strange and awful dating choice.

While some of them didn't last long, others had terrible breakups which had a significant impact on their lives as well as their careers. Let's rewind to the past and see these weird dating choices.

Take a look at the top 13 weirdest celebrity couples who used to date in the 2000s.

1 Matthew McConaughey and Janet Jackson.

They met at an awards show in 2002 and started dating afterward.

2 Ashley Olsen and Lance Armstrong.

Despite a 15 year age gap, they dated in 2007.


3 Hilary Duff and Joel Madden.

They had an age gap of 9 years when they dated from 2004 to 2006. Hilary was only 16, while Joel was 25.

4 Taylor Swift and John Mayer.

They dated for the years 2009 and 2010. There is also a song written by Taylor Swift called Dear John which was dedicated to him.


5 Tom Green and Drew Barrymore.

The two of them were married, although it lasted only six months.

6 Lindsay Lohan and Wilmer Valderrama.

After Lindsay had made an appearance on That 70s shows, they started dating.


7 Ryan Gosling and Sandra Bullock.

They dated in 2003, although they had a huge age gap of 16 years. Sandra was 37 then while Ryan was just 21.

8 Matt Damon and Winona Ryder.

They were extremely popular as a couple in 2002, and they didn't hesitate to show their love for each other in public.


9 Kim Kardashian and Nick Lachey.

In 2005, Nick and Jessica Simpson had a dramatic divorce, and soon after, Kim started dating Nick, although it only lasted for a short while.

10 Kim Kardashian and Nick Cannon.

That same year, in 2004, Kim dated Nick for five months.


11 Ryan Reynolds and Alanis Morisette

According to Alanis, she was responsible for the break-up between Ryan and Scarlet. The two were engaged for some time, but they broke up after a while.

12 Brittany Murphy and Ashton Kutcher.

The two started dating on the set of Just Married, where they were co-stars.


13 Rihanna and Shia LaBeouf.

The two went on a single date in 2007, but they didn't continue seeing each other since the date didn't turn out to be so good. However, they are still friends.


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