Celebrities never fail to surprise us. Whether it’s risky movie roles, unexpected career moves or shocking confessions. But let’s be honest for a moment: what we’re always dying to know is who’s dating who and who’s just broke whose heart. While the mammoth of celebrity couples, Brangelina, shocked us this week with the announcement of separation, we’d like to take a moment and remember the couples we can’t believe matched in the first place.

 

Drew Barrymore and David Arquette

Getty

David Arquette certainly had fun on the set of the Scream trilogy. Not only did he marry his on-screen love interest Courteney Cox, but he recently revealed that he had a thing going on with Drew Barrymore, too. Although sources reveal Arquette and Barrymore dated long before they had to run away from the Ghostface together — they were an item in 1991.

 

Jessica Simpson and Jensen Ackles

Getty

Apparently the Supernatural star was “Irresistible” for Jessica Simpson as they dated back in the '90s. The romance didn’t last long long — Simpson later revealed that Ackles cheated on her with LeAnn Rimes.

 

Sarah Jessica Parker and Robert Downey Jr.

Getty

Long before Downey Jr. was saving the world as Iron Man and Parker was clicking her Manolo Blahnik’s as Carrie Bradshaw, they were the tightest Hollywood couple from 1984 to 1991, before Downey’s addiction and misbehaving took the best of their relationships. Last year they had a reunion meeting, which gave both much-needed closure. 

 

Ryan Reynolds and Alanis Morisette

Jeff Kravitz/FilmMagic

Isn’t it ironic? Canadian pride all the way! Ryan Reynolds dated Alanis Morisette from 2002 to 2007, and their break-up inspired Morisette’s album Flavors of Entanglement. But both got their happy endings: Reynolds ended up with Blake Lively and Morisette married musician Mario Treadway.

 

Robbie Williams and Cameron Diaz

Rex

The British popstar and American moviestar met in 2003 and had a brief fling, but Diaz didn’t disappear from Williams’ life completely — Charlie's blonde angel later bumped into him and convinced him to reunite with his then-girlfriend soon-to-be-wife Ayda Field. An angel indeed!

 

Winona Ryder and Matt Damon

Getty

Winona Ryder and Gwyneth Paltrow’s famous falling-out is well documented, but Ryder and Matt Damon’s romance is often forgotten. Damon was introduced to Ryder by her then-friend Paltrow and the couple really hit it off and dated for two years.

 

Ryan Gosling and Sandra Bullock

WireImage

Ryan Gosling had his bad boy swag early on. In 2002 he starred in Murder by Numbers alongside Sandra Bullock and the two actors began dating. The romance lasted for a year but left a good impression on Gosling, who later called Bullock one of his “greatest girlfriends of all time.”

 

Christina Applegate and Brad Pitt

Getty

Yes, Pitt always had a thing for actresses, even before all of his Aniston/Jolie shenanigans. But to be fair, He didn’t exactly "date" Applegate, as their only publicly documented date didn’t even finish. The two went together to the MTV Movie Awards in 1989, but Christina ditched her date for another (still unrevealed) celebrity. Very classy, Christina, very classy.

 

Josh Hartnett and Penelope Cruz

Getty

Back in 2007 these two beautiful people made tabloids devour on the details of their extravagant romantic night out in New York. Sadly, that was also the last time they were seen together.

 

Bradley Cooper and Jennifer Esposito

Kevin Mazur/WireImage for Turner

Several years before his big Hollywood break, Bradley Cooper was dating Jennifer Esposito and the pair went as far as marrying each other in 2006, only to divorce a year later and make Jennifer vaguely describe her unmentioned partner as “cold” in her memoir. Ouch.

 

Kiefer Sutherland and Julia Roberts

WireImage

These two rising filmstars weren’t just dating — they were about to tie the knot, before the rumors of Sutherland’s infidelity tore them apart. How can you cheat on a pretty woman like that?!

 

Fergie and Justin Timberlake

Getty

There’s a reason these two asked “Where Is The Love?” together in 2003, as by that time their romance was long time dead. 16-year-old Justin dated 23-year-old Fergie in 1996 when both were just ambitious showbiz newcomers. Luckily, they've stayed friends even after both hit the big time.

 

Conan O’Brien and Lisa Kudrow

Getty

Funny people stick together, right? When both were just starting to laugh their way up in the show business, O’Brien and Kudrow decided to give a little romance a try. It didn’t work out but neither of them seem bitter about it.

 

Seal and Tyra Banks

Getty

Seal really can’t stay away from fashion reality show hosts, can he? Before becoming a tight union with the future Project Runaway boss Heidi Klum, he had a fling with future America’s Next Top Model diva Tyra Banks.

 

Jean Claude Van Damme and Kylie Minogue

Capcom

In the '90s Kylie Minogue was pursuing a movie career, and that’s how she landed on the same set as B-movie superstar Jean Claude Van Damme in 1994’s Street Fighter. The two kicked it off (pun intended) quickly and had a short but lovely fling in Thailand. 

 

Enrique Iglesias and Sofia Vergara

Sony/Getty

Before becoming the highest paid actress on television, Vergara was spending time with the Spanish hitmaker Enrique Iglesias in the late '90s. Yes, that was when Iglesias was still rocking his trademark mole.

 

Britney Spears and Fred Durst

Getty

Everytime we’re remembering this pairing, we can’t really imagine how that was possible. Britney was entering her wicked phase when she was often see in the company of Limp Bizkit's frontman. When asked about the romance at the time, Britney said she barely knew the guy. “I just guess at the time it was taboo for a guy like me to be associated with a gal like her,” Durst later commented.

 

Moby and Natalie Portman

Getty

Forward-thinking musician and beloved Star Wars star dated for a bit in early 2000s. Moby later commented: "As far as the very brief affair I had with Natalie, it's made me the target of a lot of nerd wrath. You can't date Luke Skywalker's mom and not have them hate your guts.”

 

Tom Cruise and Cher

Rex

We're certainly having a hard time imagining these two together, but apparently their short-lived romance back in the mid-80s left a pretty lasting aftertaste. The singer, who was 39 when she was dating the 23-year-old rising movie star, named Cruise one of her “top 5 lovers” on Andy Cohen’s show several years ago.

 

Colin Farrell and Elizabeth Taylor

Getty

A story that sounds straight out of a Hollywood movie, Colin Farrell met Elizabeth Taylor in the hospital and was enchanted by the actress. As he later confessed to Ellen, the two became phone buddies and Farrell likes to think that he was the last romantic interest of the legendary actress. That explains why Farrell was present at Taylor’s funeral.