Cast your mind back a few years ago, and you’ll still have trouble remembering that these celebrities once dated. After all, the Hollywood conveyor belt is a cruel one, and it seems every year there’s a whole host of younger and prettier actors attempting to dethrone Brad and Angelina from their perch, but these beautiful faces have stood the test of time.
Yes, you’ll recognise all of them, but who they dated in the past will probably surprise you.
Here are 15 examples.
1. Josh Hutcherson and Vanessa Hudgens
You probably can’t remember Journey 2: Mysterious Island, the film which brought the two young actors together, and it’s even more likely you didn’t know that they dated.
A romance developed on set but had finished by the time the promotional tour was underway (awkward). Looking back, Hutchinson said, “We were [dating] at one point, but she broke my heart. No, I’m just kidding*, that was a while ago, we’re really good friends now.”
If you say so, Josh…
2. Ashton Kutcher and January Jones
Ashton Kutcher is no stranger to attracting beautiful women, and before he married his first wife, Demi Moore, Kutcher embarked on a three-year relationship with January Jones in 1998 shortly after signing a modelling contract after finishing runner-up to Josh Duhamel in a local competition.
Both were little known to Hollywood when they started their relationship, but though Kutcher would go on to great success in Hollywood, Jones’ acting career took longer to materialise, which may have been because Kutcher reportedly told her she shouldn’t pursue acting because she wasn’t very good at it which is rich coming from a sub-par actor like himself.
3. Tom Cruise and Cher
Two of Hollywood’s most quirky personalities got together way back in 1987, right when a fresh-faced Cruise was starting out in his quest for La La Land domination.
Funnily enough, Cher described Cruise as “shy” and admitted that despite the 16-year-age difference, she was “crazy about him.”
4. Shia LaBeouf and Hilary Duff
Remember when these two were on our screens as cute childhood stars? They were adorable, right? Well, it appeared being cute child stars was all they had in common.
According to Shia, he described the one date they went on as ‘the worst date either of us has ever had’.
5. Robert Downey Jr. and Sarah Jessica Parker
Robert Downey Jr has long put his wild, and hedonistic playboy days behind him since going sober and marrying producer Susan Downey, but back in his younger days, it appeared that no woman was off limits for the Iron Man star.
One such woman was Sarah Jessica Parker, most known for her role as Carrie Bradshaw on HBO’s Sex and the City.
However, their relationship suffered because of Robert’s substance abuse issues, and he always has positive things to say about their relationship. “She provided me a home and understanding. She tried to help me,” he remembered in one interview. “She was so miffed when I didn’t get my act together. Sarah Jessica would pull me out of a hangover, and we’d go pick out furniture together. She is a force of nature!”
6. Liam Neeson and Helen Mirren
Liam Neeson tragically lost his wife, Natasha to a skiing accident in 2009 though long before he met the late Natasha, he was in a four-year relationship with the British starlet, Helen Mirren.
Beginning a relationship in 1980 having met on the set of the film Excalibur, Mirren explained that the complicated breakup after four years together meant that “It was difficult to let go”.
7. Anthony Kiedis and Heidi Klum
Most rock stars date supermodels and Anthony Kiedis, the super cool frontman of the Red Hot Chilli Peppers is no exception to that rule.
Spotted together looking all starry-eyed in Australia, a brief romance is rumoured to have occurred before Klum got engaged to the singer Seal.
8. Seal and Tyra Banks
Speaking of Seal, supermodel Tyra Banks shared a brief rendezvous with the hitmaker back in 1996.
Only appearing in public once, it seems Seal has a penchant for supermodels having married the German supermodel Heidi Klum in 2005.
9. Leonardo DiCaprio and Naomi Campbell
This stud and Oscar-winning actor has seemingly slept with nearly every model and supermodel out there since gaining global fame for his role in James Cameron’s blockbuster extraordinaire, Titanic.
Of course, Leo’s dating history is nothing new, but few are aware that he briefly dated the British supermodel Naomi Campbell in 1995 before he called things off with the model after landing a rather notable role in Titanic, though the two remain good friends.
10. Lance Armstrong and Ashley Olsen
Lance Armstrong’s fall from grace is one of the most notable in recent history, and he is certainly a warning of what can happen when too much power goes to someone’s head after it emerged that he had illegally doped throughout his cycling career while threatening anyone who dared speak out against him.
That said, we doubt Ashley Olsen had much knowledge of her then boyfriend’s secret world, and the two shared a brief romance in 2007 a year after Armstrong’s split from the country music star, Sheryl Crow.
11. Robbie Williams and Cameron Diaz
While Robbie Williams has sold countless records around the world, one of the markets he never broke was America. With that said, that didn’t stop the Angles star from buying a Los Angeles mansion and socialising with the Hollywood glitterati for many years.
Williams even started up his very own soccer team, Los Angeles Vale F.C upon moving to Tinseltown, and was soon spotted holding hands with none other than Hollywood megastar Cameron Diaz in 2003. Though it didn’t last long, Cameron reportedly played a significant role in convincing Robbie to stick it out with his now wife, Ayda Field when they were going through hard times, with Field being good friends with the star.
12. Moby and Natalie Portman
Arguably the most random and unlikely couple on this list, everyone’s favourite DJ from the 90s dated the actress in 2001, but as was this case with his music career, he received a lot of abuse over the relationship.
According to the man himself, the abuse was that time directed from nerds as opposed to snobby music aficionados. “As far as the very brief affair that I had with Natalie,” he said. “It’s made me a target of a lot of nerd wrath. You don’t date Luke Skywalker’s mom and not have them hate your guts.”
13. Ryan Gosling and Sandra Bullock
Before Ryan was cast in the Nicholas Sparks’ melodrama The Notebook, he wasn’t considered a conventionally attractive actor, and many thought he was punching above his weight when he briefly dated Sandra Bullock in 2002.
Meeting on the set of the movie, Murder by Numbers, Bullock was 16 years his senior and was left heartbroken when he reportedly called things off with the actress.
14. Christian Bale and Drew Barrymore
Christian Bale was deemed good looking enough to play the attractive, albeit highly narcissistic banker Patrick Bateman in the gory 1999 classic, American Psycho, so his looks have never been in doubt, just like his acting abilities, but he is nonetheless a fearsome dude (listen to his famous rant to a production assistant if you haven’t already) so few would have paired him with the lovable rouge, Drew Barrymore.
In all truth, they went on only one date, but it still seems odd that they thought they’d get along in the first place. As for the date itself, in true Christian Bale style, they saw a horror film. Speaking about it, Bale recalled, “We went to see some bloody awful horror film, and that was the end of it. She never called again.”
15. Matthew Perry and Heather Graham
Friends star Matthew Perry hooked up with blonde bombshell Heather Graham in 2003, but it was a brief fling, to say the least.
Indeed, the relationship was so short-lived the couple didn’t even have time to go public with it before they split.
