17 Throwback Celeb Couples That Are So ’00s It Hurts

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Pour one out for the celeb pairings we loved and lost.

1.

Nick Lachey and Jessica Simpson


MTV

In the early ’00s, Nick and Jessica were the couple. Long before Twitter was invented and Chrissy Teigen harnessed its power, Jessica Simpson had the relatable rich girl thing down pat. Through their reality show Newlyweds, the world became invested in Nick and Jessica’s romance — until it all came crashing down in 2005 and they divorced.

2.

Ryan Cabrera and Ashlee Simpson


MTV

Jessica wasn’t the only Simpson with a reality show and a high-profile relationship (or two). Her little sister Ashlee had The Ashlee Simpson Show, on which her romance with musician Ryan Cabrera unfolded. It was a simple time, before the Kardashians cornered the celeb TV market.

3.

Carson Daly and Tara Reid


Universal

He was the host of MTV’s TRL; she was a staple of the Hollywood party scene while starring in American Pie and Josie and the Pussycats. It was a match made in ’00s gossip heaven.

4.

Brittany Murphy and Ashton Kutcher


20th Century Studios

This one is extra sad to look back on. Brittany and Ashton met on the set of Just Married and looked so loved-up off screen that dating rumors soon followed. They seemed to stay friends even after they parted ways.

5.

Aaron Carter and Hilary Duff


Lucy Nicholson / Getty Images

Ah, the Disney drama of the early ’00s. Aaron Carter was the golden boy who two-timed on Hilary Duff with Lindsay Lohan. But the pair still dated for three years, and he seemed to have trouble letting her go, repeatedly declaring his undying love for her over the years.

6.

Chris Evans and Jessica Biel


Destination Films

Chris Evans dated Jessica Biel before he became Captain America, when he was still giving off major dirtbag vibes (to be fair, everyone gave off dirtbag vibes in the early ’00s). They were actually together for a decent chunk of time — from 2001 to 2006.

7.

Wilmer Valderrama and Lindsay Lohan


Fox

Wilmer Valderrama hooked up with just about every young ~starlet~ in the ’00s, and Lindsay Lohan’s love life was prime gossip material, so the two of them getting together — albeit briefly — was the ultimate pairing for anyone following celeb gossip blogs back when celeb gossip blogs were a thing.

8.

Scarlett Johansson and Josh Hartnett


Lionsgate

Remember Josh Hartnett? He was a whole thing in the late ’90s/early ’00s. He and Scarlett Johansson met on the set of The Black Dahlia and were a very hot couple for a very brief period of time.

9.

Nick Jonas and Miley Cyrus

10.

Jennifer Lopez and Diddy


MTV

Back when he was still known as Puff Daddy, J. Lo and Diddy had a high-profile relationship. It started in 1999 but lasted until 2001, turning them into one of the defining celeb couples that kicked off the decade. He was even with her when she wore THAT green dress on the red carpet.

11.

Jennifer Lopez and Ben Affleck


Kevin Winter / Getty Images

J. Lo’s lovelife high-key dominated the tabloids in the ’00s, and her relationship with Ben Affleck eclipsed every other. They were the OGs of couple names — you couldn’t escape the phenomenon that was Bennifer. What a time.

12.

Justin Timberlake and Britney Spears


E!

Justin and Britney’s romance started in the ’90s, but it lasted into the early ’00s and is to this day one of the most iconic celeb couplings of all time. They grew up together, and their relationship seemed like a dream, right down to their matching double (triple? quadruple?) denim.

13.

Kevin Federline and Britney Spears


Vince Bucci / Getty Images

Kevin Federline swooped into Britney’s post-Timberlake life and hitched himself firmly to her wagon. The pair got engaged after just three months of dating, got married two months later, and were divorced two years after that. In that time, they had two kids and one reality show.

14.

Tom Cruise and Katie Holmes


Mj Kim / Getty Images

Who could forget the infamous couch-jumping incident of 2005? The moment Tom and Katie revealed they were a couple, it was an instant media frenzy — one they happily fed for a long time.

15.

Rachel Bilson and Adam Brody


Fox

Seth and Summer were the superior ship on TV in the ’00s, and the fact that they dated in real life just made it all the more exciting. When Rachel and Adam broke up in 2006, it was almost as devastating for fans as it was for them.

16.

Ryan Gosling and Rachel McAdams


Kevin Winter / Getty Images

If Seth and Summer/Rachel Bilson and Adam Brody were the it couple of ’00s TV, then Rachel McAdams and Ryan Gosling were the movie equivalent thanks to their iconic pairing in The Notebook and subsequent real-life romance. Ryan once even said that his and Rachel’s love story was more romantic than Noah and Allie’s in The Notebook. Frankly, they’re probably more over this relationship than the rest of us are.

17.

Robert Pattinson and Kristen Stewart


Ian Gavan / Getty Images

As Rachel and Ryan’s love story waned, a new set of co-stars-turned-lovebirds took their place: RPattz and KStew (why did we do this to everyone’s names in the ’00s???). The real-life Edward and Bella kept their romance under wraps for a long time, but it nevertheless delighted Twilight fans and had everyone analyzing their every move.

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