15 Celebrity Couples You Probably Forgot Dated In The 2000s

The aughts were a magical time for all of us. So magical, in fact, that we may have collectively repressed some of the actual events which occurred in the 2000’s. For example: butterfly clips? Totally pushed to the back of my mind, forever and ever, amen.

There are also plenty of celebrity relationships which somehow managed to sneak by, unnoticed, during the 2000’s. Looking back, I don’t know how we could have ignored such magnificent partnerships … but, considering some of us were just coming of age during the aughts, I suppose it’s excusable.

Here are just a few blast-from-the-past relationships that will blow your tiny little brain — or, more accurately, will probably make you say “Holy sh*t, I forgot about those two!”

Even though these romantic relationships no longer exist, they will live on forever in our pure 2000’s hearts.


Related-ish: 11 Early 2000’s Songs For Your Inner Angsty Teen


1. Tom Cruise and Sofia Vergara

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This bizarre pair dated back when Cruise was trying out different celebrity actresses to be the next Mrs. Tom Cruise (with the help of the Church of Scientology, obviously). Not surprisingly, this romantic pairing didn’t last terribly long.

2. Anne Hathaway and Topher Grace

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How did we forget such a wide-eyed and eager pairing?? Topher and Anne reportedly dated from 1999 to 2001, though they apparently still remain friends.

3. Jared Leto and Paris Hilton

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Okay, so these two didn’t officially date — they just fooled around back in 2008. But STILL. Can we just take a moment to appreciate how truly amazing this partnership could have have been?

4. Ryan Gosling and Sandra Bullock

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Okay, I love both of these celebrity humans, so reminiscing about this breakup is extremely bittersweet. These two dated from 2002 to 2003, before Gosling dated Rachel McAdams.

5. Kim Kardashian and Nick Lachey

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These two dated in 2006 (briefly), but apparently things ended on a sour note as Lachey later claimed that Kim K used him to get famous.

6. Ryan Reynolds and Alanis Morissette

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These two began dating in 2002, and became engaged in 2004. Sadly, they called off their engagement in 2007 (which probably resulted in some really moody music, honestly).

7. Simon Cowell and Carmen Electra

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These two didn’t exactly ~*date*~, but they definitely smooched a little bit, and as far as I’m concerned, that’s still bizarre enough to count.

8. Janet Jackson and Matthew McConaughey

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Um … alright, alright, alright? (Sorry.) These two apparently had a brief fling in 2002, which is amazing, and also, how did I never know this??

9. Ashley Olsen and Lance Armstrong

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Lance Armstrong started dated Ashley Olsen in 2007 (yes, she is 15 years younger than him, thank you for asking.) Apparently, Armstrong’s friends were unsupportive of the relationship, warning him that the unusual romance would damage his image. Fortunately, I think he eventually managed to damage his image all by himself!

10. Ashton Kutcher and Brittany Murphy

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This rambunctious pair dated back in 2003, shortly after filming their rom-com Just Married (which you totally watched, don’t pretend you didn’t). Following Murphy’s death in 2009, Kutcher tweeted: “2day the world lost a little piece of sunshine. My deepest condolences go out 2 Brittany’s family, her husband, & her amazing mother Sharon. See you on the other side, kid.”

11. Natalie Portman and Moby

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Oh MAN, this relationship was truly nerdtastic and I am sorry that it has been lost to the sands of time. The two briefly dated in 2001, and apparently specialized in awkwardly holding cakes together.

12. John Mayer and Jessica Simpson

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Ugh. Jessica. Why did you have to run into the seedy arms of John Mayer following your divorce? Have the tabloids told you NOTHING? These two dated from 2006 to 2007. Following the split,  Mayer (naturally) gave a tell-all interview to Playboy which described the details of their sexual relationship.

13. Rihanna and Shia LeBeouf

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Okay, these two apparently only went one ONE DATE in 2007, but in my opinion, that still counts as “dating.” The date was unsuccessful, but the two apparently decided to remain friends.

14. Wilmer Valderrama and Mandy Moore

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How did this even happen? Mandy is so great, and Wilmer is so … deplorable. He actually gave an interview with Howard Stern in which he claimed to have taken Moore’s virginity.

Calm down, Wilmer. Nobody cares. You aren’t famous anymore.

15. 50 Cent and Chelsea Handler

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This one just totally blows my mind, wile simultaneously fulfilling my wildest dreams. Chelsea Handler apparently had a “very casual” relationship with 50 Cent in 2009 — and now that I’m aware of this information, that year will never be the same, ever again.

Related-ish: 19 Toys That’ll Kick You Right In The 2000’s

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