1. Justin Timberlake and Fergie
Back in 1996, way before they became the pop stars we know and love, Justin Timberlake and Fergie were a thing. Proving herself to be quite the cougar (even before that was a thing), a 23-year-old Fergie nabbed herself a 16-year-old Justin and probably taught him everything* he knows.
*Probably not everything.
2. Alexander Skarsgård and Amanda Seyfried
These two dated very briefly in the wake of Amanda’s high-profile split from Dominic Cooper. Despite the fact that they would’ve had the most genetically perfect children imaginable, things didn’t work out.
Amanda has since explained that although Alexander was ‘super-funny,’ she felt ‘too involved with Dom’ for things to go any further than a casual few dates.
3. Moby and Natalie Portman
Probably the most unlikely couple of all time, Moby and Natalie Portman dated in 2001, but poor old Moby received a lot of abuse over the relationship.
He has since explained: “As far as the very brief affair that I had with Natalie, 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.”
4. Ryan Gosling and Sandra Bullock
Ryan Gosling and Sandra Bullock met on the set of the movie Murder by Numbers. Despite her being 16 years his senior, the pair dated between 2002–2003 before what was rumoured to be a messy breakup leaving Sandra ‘broken-hearted’.
On an unrelated note, just look at his cute little young face. Who knew he’d blossom into a complete and utter SEX GOD.
5. David Arquette and Drew Barrymore.
Before he became Mr Courteney Cox (for a while,) David Arquette had a teenage romance with Drew Barrymore in 1991, when he was 19 and she was 16.
6. Christian Bale and Drew Barrymore
In what will go down in history as the shortest celebrity relationship of all time, Christian Bale and Drew Barrymore went on just ONE date, 20 years ago.
Christian explained: “We went to see some bloody awful horror film, and that was the end of it. She never called again.”
7. Lance Armstrong and Ashley Olsen
Despite being a rather unlikely pair, Lance Armstrong and Ashley Olsen had a short-lived fling back in 2007. They were even snapped publicly kissing and leaving a hotel together in the early hours of the morning, but things fizzled out shortly afterwards.
8. Robbie Williams and Cameron Diaz
Robbie Williams and Cameron Diaz were spotted kissing and holding hands on a Santa Monica beach in 2003.
Before their romance ended, Robbie even took Cameron for some go-karting fun in Germany, which is, of course, every woman’s idea of a dream date.
9. Tobey Maguire and Rashida Jones
These two dated for three years between 1997–1999. However, Tobey broke up with Rashida (just…WHY?!) just before he landed the role of Spider-Man which catapulted him to fame.
10. Ryan Reynolds and Alanis Morissette
Long before marrying two blonde bombshells (Scarlett Johansson and Blake Lively), Ryan Reynolds was engaged to Alanis Morissette. The pair were together between 2002–2007 which is practically a lifetime in showbiz.
And just LOOK at how in love they were.
11. Matthew Perry and Heather Graham
Chandler from Friends hooked up with Heather Graham in 2003 — but they didn’t even have a chance to go public with their relationship before it ended.
12. Leonardo DiCaprio and Naomi Campbell
Proving that he always has had a penchant for supermodels, Leonardo DiCaprio dated Naomi Campbell back in 1995. They split up right before he landed a role in a little film about a boat that you may have heard of.
13. Nick Lachey and Kim Kardashian
After his high-profile divorce from Jessica Simpson, Nick Lachey dated Kim Kardashian when she was trying to find fame as an L.A. socialite.
In fact, her desire to be famous was what made Nick call things off, with him claiming that she set up paparazzi photos of their date.
He said: “That’s one way to interpret it. Let’s just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside.”
14. Nick Cannon and Kim Kardashian
Before Kanye West and Mariah Carey came along and stole their hearts, a fresh-faced Kim Kardashian and Nick Cannon dated for a few months in 2006.
15. Jason Schwartzman and Zooey Deschanel
Jason Schwartzman was Zooey Deschanel’s first boyfriend, and they dated for three years before she found fame as an actress. They split amicably with neither ever making any public comment about their relationship.
16. Josh Hutcherson and Vanessa Hudgens
Josh Hutcherson and Vanessa Hudgens began dating during the making of their movie Journey 2: Mysterious Island.
However, he was awkwardly forced to admit that their romance was over during the promotional trail for the film. He 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.”
17. Ashton Kutcher and January Jones
Back when he was merely losing cars, and long before his relationships with Demi Moore and Mila Kunis, Ashton Kutcher dated January Jones.
The pair were together between 1998–2001, but Ashton wasn’t exactly the most supportive boyfriend. He reportedly discouraged January from pursuing her dream of acting, telling her she wouldn’t be any good at it.
She had the last laugh, though, landing a role in Mad Men years later.
18. Tom Cruise and Cher
Despite the 16-year age difference, Tom Cruise and Cher dated in 1987, when she was at the peak of her career and he was just beginning his. Cher has since described Tom as ‘shy’ and admitted that she was ‘crazy about him’.
19. Shia LaBeouf and Hilary Duff
Shia LaBeouf and Hilary Duff abandoned any hope of a relationship after just one date. He’s never gone into details about the disastrous meet-up, but he has labelled it ‘the worst date either of us has ever had’.
20. Matthew Morrison and Kristen Bell
These two met and dated for a while during their time at NYU. Speaking about their relationship many years later, Kristen explained: “I actually went to college with Matt Morrison. We actually dated very briefly, so I’ll have to say maybe Matt Morrison is my favourite part of Glee for various reasons.”
21. Robert Downey Jr. and Sarah Jessica Parker
These two dated for years back in the 1980s, but his drink and drug abuse put a strain on their relationship.
He has since explained: “She provided me a home and understanding. She tried to help me. 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!”
22. Anthony Kiedis and Heidi Klum
In what had the potential to be the most achingly cool pairing of all time, Red Hot Chilli Peppers frontman Anthony Kiedis dated Heidi Klum briefly in 2002. They were spotted being very affectionate with one another during a trip to Australia, but it didn’t seem to blossom and before long Heidi was engaged to Seal.
23. Seal and Tyra Banks
Seal romanced Tyra Banks, 11 years his junior, back in 1996. The pair kept their romance fairly under wraps, only going out as a couple once, but split within a year.