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The 20 Weirdest Couples Of The Early(ish) 2000s

And you thought Gwen and Blake were random.

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1. Janet Jackson and Matthew McConaughey

Apparently they met at the 2002 Grammys and had a brief fling. Go figure?!
Frank Micelotta Archive / Getty Images

Apparently they met at the 2002 Grammys and had a brief fling. Go figure?!

2. Cameron Diaz and Jared Leto

Just look at these two lil' blondies! In 2002, The Telegraph called them one of "Hollywood's most photogenic, but least photographed couples." Lucky for us, some paparazzi caught them literally shopping for some plants back in the day. That's how you know shit got serious. RIP and miss you!
FameFlyNet

Just look at these two lil' blondies! In 2002, The Telegraph called them one of "Hollywood's most photogenic, but least photographed couples." Lucky for us, some paparazzi caught them literally shopping for some plants back in the day. That's how you know shit got serious. RIP and miss you!

3. Britney Spears and Fred Durst

OK this one was random AF and I'm waiting for Britney's (hopeful) tell-all in 2025 where she REALLY breaks it down for us. As it stands, Britney basically claims that Fred was obsessed with her; MEANWHILE, Fred says that it was a mutual relationship. Here's what Britney said to Glamour magazine via People magazine in 2003:"I think him for me, but not me for him. He's said some pretty amazing things about me. But, um, I think he leaped in too deep, too quick."
US Weekly

OK this one was random AF and I'm waiting for Britney's (hopeful) tell-all in 2025 where she REALLY breaks it down for us.

As it stands, Britney basically claims that Fred was obsessed with her; MEANWHILE, Fred says that it was a mutual relationship.

Here's what Britney said to Glamour magazine via People magazine in 2003:

"I think him for me, but not me for him. He's said some pretty amazing things about me. But, um, I think he leaped in too deep, too quick."

4. Wilmer Valderrama and Mandy Moore

They dated from 2000 to 2002 and in 2006 Wilmer told Howard Stern that she lost her virginity to him. Classy!
Kevin Winter / Getty Images

They dated from 2000 to 2002 and in 2006 Wilmer told Howard Stern that she lost her virginity to him. Classy!

5. Hilary Duff and Joel Madden

Evan Agostini / Getty Images

She was 16 and he was 24 when they started dating. I HAD NO idea. Like what?

6. Drew Barrymore and Tom Green

Even Tom Green thought this was random. In an Oprah: Where Are They Now special, Tom said: "It was just a very short period of time that I had a brief marriage. I don't really tend to talk about it that much comfortably or publicly. All of that was part of that sort of crazy, whirlwind of a time."
Lucy Nicholson / AFP / Getty Images / Via huffingtonpost.com

Even Tom Green thought this was random. In an Oprah: Where Are They Now special, Tom said: "It was just a very short period of time that I had a brief marriage. I don't really tend to talk about it that much comfortably or publicly. All of that was part of that sort of crazy, whirlwind of a time."

7. Megan Fox and David Gallagher

Yes, that is the kid from 7th Heaven, yes that is Megan Fox, and yes they actually dated.
Jon Kopaloff / Getty Images

Yes, that is the kid from 7th Heaven, yes that is Megan Fox, and yes they actually dated.

8. Vivica A. Fox and 50 Cent

This year, Vivica A. Fox told Meredith Vieira that 50 Cent was the love of her life. They dated in 2003.
Evan Agostini / Getty Images

This year, Vivica A. Fox told Meredith Vieira that 50 Cent was the love of her life. They dated in 2003.

9. Hilary Duff and Aaron Carter

This one isn't so rare — I just wanted to post this picture of the two of them together because it's so weird that they actually were a thing.
Most Wanted / Most Wanted/Flynet

This one isn't so rare — I just wanted to post this picture of the two of them together because it's so weird that they actually were a thing.

10. Deryck Whibley and Paris Hilton

That guy from Sum 41 and Paris Hilton. Yup, they dated.
Rodrigo Varela / WireImage

That guy from Sum 41 and Paris Hilton. Yup, they dated.

11. Paris Hilton and Mark McGrath

This is funny.From Howard Stern: Mark claimed he wasn't able to please Paris in the bedroom due to his small penis: "I'm Irish, man. I got the curse...I did my best...it was sloppy, you know, 3 a.m." Howard asked if Paris laughed at his penis, but Mark denied it: "She didn't laugh at me. She sort of ran screaming."
J. Vespa / WireImage

This is funny.

From Howard Stern:

Mark claimed he wasn't able to please Paris in the bedroom due to his small penis: "I'm Irish, man. I got the curse...I did my best...it was sloppy, you know, 3 a.m." Howard asked if Paris laughed at his penis, but Mark denied it: "She didn't laugh at me. She sort of ran screaming."

12. Moby and Natalie Portman

Moby told Spin: "We dated so briefly that you almost can't call it dating. She's one of my close friends, and has so much more character and substance than most people I know. At this point, she's like my cousin. If we were to find ourselves making out again, it would feel a little incestuous."
WireImage

Moby told Spin: "We dated so briefly that you almost can't call it dating. She's one of my close friends, and has so much more character and substance than most people I know. At this point, she's like my cousin. If we were to find ourselves making out again, it would feel a little incestuous."

13. Anthony Kiedis and Heidi Klum

They dated in 2002 for a hot minute and here is a picture of them eating pizza together.

They dated in 2002 for a hot minute and here is a picture of them eating pizza together.

14. JC Chasez and Tara Reid

This one is tricky. They were apparently together in like 2002 for a hot minute when JC had that "Blowin' Me Up" song. This picture is from 2005. They definitely didn't date for three years, so who knows?
Peter Kramer / Getty Images

This one is tricky. They were apparently together in like 2002 for a hot minute when JC had that "Blowin' Me Up" song. This picture is from 2005. They definitely didn't date for three years, so who knows?

15. Lenny Kravitz and Nicole Kidman

In a time before Twitter and Instagram, 2003, Lenny and Nicole had to finally come clean about their relationship after they were spotted by random people together a bunch of times. A rep told People, "They're very close. He's very important to her."
New York Daily News Archive / Getty Images

In a time before Twitter and Instagram, 2003, Lenny and Nicole had to finally come clean about their relationship after they were spotted by random people together a bunch of times. A rep told People, "They're very close. He's very important to her."

16. Kim Kardashian and Nick Cannon

Classic. Just classic.
Michael Buckner / Getty Images

Classic. Just classic.

17. Lindsay Lohan and Samantha Ronson

Honestly, so memorable and random. In 2012, Lindsay told Us Weekly that they broke up because "two toxic people cannot be together." Ouch.
Fameflynet

Honestly, so memorable and random. In 2012, Lindsay told Us Weekly that they broke up because "two toxic people cannot be together." Ouch.

18. Ryan Gosling and Sandra Bullock

They fell in love in 2002 on the set of the movie Murder by Numbers. End of story.
Francois Guillot / AFP / Getty Images

They fell in love in 2002 on the set of the movie Murder by Numbers. End of story.

19. January Jones and Josh Groban

I...don't even know what to make of this one.
Vince Bucci / Getty Images

I...don't even know what to make of this one.

20. Paris Hilton and Nick Carter

They dated for like 10 months in 2004 and produced pictures like the one above. In his book released in 2013, Nick said:"Paris was the worst person in the world for me to hook up with. [She] fed my worst impulses as far as partying."Paris responded by telling Access Hollywood: "I don’t believe I was a negative influence on Nick, we dated for a very short period of time almost 10 years ago and when we met he was already a successful pop star, I’m pretty sure that was the only thing influencing him at the time. I’m glad he got help for his problems and wish him all the best."THE DRAMA NEVER ENDS.
Frazer Harrison / Getty Images

They dated for like 10 months in 2004 and produced pictures like the one above.

In his book released in 2013, Nick said:

"Paris was the worst person in the world for me to hook up with. [She] fed my worst impulses as far as partying."

Paris responded by telling Access Hollywood:

"I don’t believe I was a negative influence on Nick, we dated for a very short period of time almost 10 years ago and when we met he was already a successful pop star, I’m pretty sure that was the only thing influencing him at the time. I’m glad he got help for his problems and wish him all the best."

THE DRAMA NEVER ENDS.

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