The 2000s: when #couplegoals was all about sticking posters of the cutest celeb twosomes on your bedroom walls, or eagerly waiting to see which co-stars in your favourite series would get together.
To be honest, we feel a bit nostalgic for these days. While their red carpet choices were occasionally questionable, their shows were dramatically cheesy (One Tree Hill, Gossip Girl, the list goes on), and some of these pairings were rather unexpected, their romances helped define a decade. And yes, at the time we were pretty obsessed.
Now that the 2000s is making its sartorial comeback, let’s reflect on the celebrity couples that sum up everything we loved (and would rather forget) about the 2000s.
Their romance may be over, but we will always remember how obsessed we were with these celebrity couples in the 2000s. From their (sometimes) questionable sartorial choices, to some very unexpected pairings, these are the twosomes that define the era.
Puff Daddy and Jennifer Lopez
This hip-hop duo dated from 1991 to 2001. After their breakup, Puff told The New York Daily News: “And I’m happy for her. I’ll always be there for Jennifer, whether business or personal.”
Carson Daly and Tara Reid
He may have tried to kill her in the film Josie and The Pussycats, but in reality they were dating after they met on the set of TRL in 2000. After a short engagement, they split in 2001.
Katie Holmes and Chris Klein
After dating from 2002 to 2005, and even being engaged at one point, they split and Katie went on to date Tom Cruise a few months later.
Mischa Barton and Brandon Davis
This duo dated for a year after meeting at a charity event.
Ryan Gosling and Sandra Bullock
One of the more unexpected pairings, they dated from 2002 to 2003 after meeting on the set of Murder by Numbers.
Jennifer Lopez and Ben Affleck
The most memorable element of this relationship was when Ben starred in J Lo’s ‘Jenny From The Block’ music video.
Jared Leto and Cameron Diaz
Cameron clearly has a thing for rock stars. Their romance ended in 2003 after four years of dating.
Aaron Carter and Hilary Duff
This was definitely one of the most drama-filled love triangles in celeb history. At the same time he dated Hil, he also dated Lindsay Lohan. Ouch.
Nick Lachey and Jessica Simpson
The best thing about this relationships? Their television show, Newlyweds: Nick and Jessica
Jake Gyllenhaal and Kirsten Dunst
These two got together in 2002, and even had a dog together named Atticus.
Alanis Morissette and Ryan Reynolds
The very Canadian couple dated for two years before announcing their engagement in 2004. When splitting in 2007, Alanis became the original Taylor Swift and released her breakup album Flavors of Entanglement.
Adam Brody and Rachel Bilson
When our favourite on-screen couple became a couple in 2006, we were overjoyed. However, they only lasted for three years.
Jessica Biel and Chris Evans
Before he became Captain America and she started dating Justin Timberlake, they were an item for 5 years from 2001.
Scarlett Johansson and Josh Hartnett
They met on the set of Black Dahlia, but split in 2006.
Kelis and Nas
This was one of our favourite hip-hop duos, but it wasn’t meant to be. After seven years together, four of which they were married, Kelis filed for divorce when she was seven months pregnant.
Wilmer Valderrama and Mandy Moore
How were they together? We have no idea.
Nicole Richie and DJ AM
Richie has a penchant for musicians. They dated from 2004 to 2006.
Ashlee Simpson and Ryan Cabrera
While we don’t remember this one as much, it was documented on her MTV series The Ashlee Simpson Show.
Wilmer Valderrama and Lindsay Lohan
They dated in 2004 when That 70s Show was in its prime. After their breakup, Lindsay went on to write the song ‘Speak’ on her debut album.
Kate Bosworth and Orlando Bloom
After their breakup, Kate said it was so painful she felt like she had vertigo.
Kevin Federline and Britney Spears
Ah, these Britney years when SO much happened. Before they divorced in 2006, they had two children together and documented their lives on the legendary series, Britney and Kevin: Chaotic.
Rosario Dawson and Jason Lewis
They started dating just as Lewis was ending his tenure as Smith on Sex And The City (who could ever forget him). They split up in 2006 after two years.
Tom Cruise and Sofia Vergara
We had no idea they were ever together. Apparently she ended it because she was creeped out by Tom and his Scientology devotion and let’s be honest, who isn’t.
Dita Von Teese and Marilyn Manson
After their divorce in 2006, we imagine one of the most tense times with their lawyers was splitting their enviable makeup collection. Just imagine what their bathroom must have been like.
Paris Hilton and Paris Latsis
Paris x 2 were engaged after five months of dating, but it wasn’t meant to be.
Kiera Knightley and Jamie Dornan
Before he was kinking it up in Fifty Shades, Dornan shacked up with British rose Keira Knightley before breaking up in 2005.
Joel Madden and Hilary Duff
In a Tyga/Kylie twist, Joel and Hillary dated for just over two years but didn’t go public until she turned 18. He was eight years her senior.
Macaulay Culkin and Mila Kunis
One of Hollywood’s longer lasting relationships, Mila and Macaulay were together for eight years. “We grew up together,” she told Women’s Health in 2009. “You find a steady rock in your life and that’s all you need. We have our ups and downs, but work through them.”
Brody Jenner and Kristen Cavallari
So much reality television romance. They dated for just over a year.
Claire Danes and Billy Crudup
This romance was filled with drama. Billy walked out on his seven-month pregnant partner Mary-Louise Parker in 2003 for Claire, and they lasted four years.
Mandy Moore and Zach Braff
They were super cute and dated for two years.
Ryan Gosling and Rachel McAdams
The Notebook is a lie. After their split in 2007, Gosling told GQ, “The only thing I remember is we both went down swingin’ and we called it a draw.”
Kanye West and Alexis Phifer
Just look at what Kanye is wearing. While these were the very different days before Yeezy and the Kardashian dynasty, it did give us the incredible ‘808s and Heartbreak’.
Michelle Williams and Heath Ledger
This is too sad to even discuss. They ended their relationship in 2007, and after Ledger was found dead in his apartment in 2008, Williams said: “My heart is broken.”
Paris Hilton and Stavros Niarchos
He broke up with Mary-Kate Olsen to be with Paris, but sadly it wasn’t meant to be.
John Mayer and Jessica Simpson
She was his “sexual napalm” from 2006 to 2007.
Kanye West and Amber Rose
Their breakup reportedly inspired ‘Blame Game’ on My Beautiful Dark Twisted Fantasy.
Evan Rachel Wood and Marilyn Manson
While he proposed to her onstage in Paris, they broke up before tying the knot.
Blake Lively and Penn Badgley
These on screen and real life lovers didn’t last.
Kim Kardashian and Nick Cannon
Who could ever forget their 2006 love. At least their outfits certainly sum up the era.
Mariah Carey and Nick Cannon
After a quick marriage, they split in 2008.
Jake Gyllenhaal and Reese Witherspoon
Reese and Jake became a thing just after she split from Ryan Phillipe. This year, he called her “one of the smartest, strongest people [he’s] ever met.”
John Mayer and Jennifer Aniston
They split first in 2008, got back together, and then split up again. Right now, we reckon Jennifer is SO much better off.
Cameron Diaz and Justin Timberlake
After they ended their three year relationship in 2006, they went on to star together in Bad Teacher.
Sophia Bush and Chad Michael Murray
Ah, this One Tree Hill love. After marrying in 2005, they separated just five months later proving the on-screen love we adore is not always what it cracks up to be.
