back to top

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

And you thought Gwen and Blake were random.

Posted on

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!

3. Britney Spears and Fred Durst

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."


6. Drew Barrymore and Tom Green

Lucy Nicholson / AFP / Getty Images / Via

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."


9. Hilary Duff and Aaron Carter

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.

11. Paris Hilton and Mark McGrath

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 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."


14. JC Chasez and Tara Reid

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

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."


20. Paris Hilton and Nick Carter

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."