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.
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.
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.
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.
Mandy Moore and Zach Braff
They were super cute and dated for two years.
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."
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.
Blake Lively and Penn Badgley
These on screen and real life lovers didn't last.
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."
Cameron Diaz and Justin Timberlake
After they ended their three year relationship in 2006, they went on to star together in Bad Teacher.