Celebs You Never Knew Dated

1. Penelope Cruz and Tom Cruise

Image sourceMeeting on the set of 'Vanilla Sky', when Tom was still married, they didn't go public until the premiere of 'Captain Corelli's Mandolin' in 2001.  Miss Cruz explained that she never fell in love with any of her fellow actors until filming finished.  How thoughtful!  The love story was not to be and they separated in 2004.

2. Mila Kunis and Macaulay Culkin

Image source Getty ImagesBefore she tied the knot with Ashton Kutcher, Mila dated Culkin for 11 years, from 2002 to 2011.  They first got together when the 'Black Swan' actress was only 18 and the 'Home Alone' star was 21.  Although an intense relationship, they grew out of each other as they matured but stayed friends.

3. Cameron Diaz and Justin Timberlake

Image source Getty ImagesWhen Cameron Diaz met the NSYNC frontman, at the Nickelodeon Kids' Choice Awards, there was an instant spark between them and she followed him on his tour with Christine Aguilera.  The pair dated for over 4 years and the quietly split up, until the Press, heard!

4. Alanis Morrissette and Ryan Reynolds

Image source Getty ImagesThey met in 2002 at Drew Barrymore's birthday party in 2002 and announced their engagement 2 years later.  The union lasted 3 years until they publicly broke it off, issuing a public statement to the public.  Alanis was very emotional for a long time after they separated.

5. Cindy Crawford and Richard Gere

Image source Getty ImagesThis beautiful couple clicked at a friend's BBQ and despite the 17 year age gap (she was 22 and he was 39), their love continued to sizzle and they went on to marry in 1991 at the Sin City Chapel in Vegas.  Unfortunately, it didn't last and they divorced in 1995, with much speculation as to why.

6. Anjelica Huston and Jack Nicholson

Image source Getty ImagesAfter moving back home to Los Angeles, Huston met Nicholson at his birthday party in 1973.  The 14 year age gap wasn't an issue for them and they stayed together for over 20 years.  The split was mainly, or rather wholly, due to him being unfaithful and getting Rebecca Broussard pregnant.  Naughty Jack!

7. Salma Hayek and Edward Norton

Image source Getty ImagesThe 'Fight Club' actor and 'Frida' actress dated from 1999 until 2003 after the two were set up on a blind date by their chiropractor!  Hayek credited Norton for all his help in the 2002 movie about the famous artist and the two of them remained good friends and do so to this day.

8. Tom Cruise and Cher

Image source Getty ImagesWhen this unlikely couple started a whirlwind romance, Cher was at the peak of her popularity and Cruise was first starting out.  Known for dating younger men, Cher wasn't concerned in the slightest at their 16 year age gap.  Tom finished it and Cher was heartbroken as she admitted she was 'crazy for him'.

9. Janet Jackson and Matthew McConaughey

Image source Getty ImagesAfter meeting at the 2002 Grammys,  Janet Jackson and Matthew McConaughey indulged in a short relationship which Matthew always denied, saying they were just friends.  Miss Jackson put the record straight and said they were an item but they wanted the Press to stay away from them.

10. Ryan Gosling and Sandra Bullock

Despite a 16 year age difference, 'The Notebook' star and Sandra Bullock dated in 2002 for over a year.  They met on the set of 'Murder by Numbers' and soon became a '2'.  The relationship fizzled out although Ryan has always said she was one of the best girlfriends ever.

11. Tyra Banks and Drake

Image source Getty ImagesDrake confirmed to Ellen Degeneres that he dated Tyra Banks a few times but that it was only as friends.  Tyra, on the other hand, told Oprah that they had a short relationship but called it quits due to hardly being able to see each other due to work commitments!  Who do you believe?

12. Courteney Cox and Michael Keaton

Image source Getty ImagesCourteney Cox and Michael Keaton were a coupe for 6 years during which time they would practice their lines together (is that an inuendo?)  They made a joint decision to end it although both gushed about how great the other person was - so why did they split then?

13. Kim Kardashian and Nick Cannon

Image source Getty ImagesWe know you remember they were together but we had to put this one in!  They dated in the early 2000's and split, allegedly, after Kim's sex tape with Ray J. surfaced.  Cannon brushed himself down and started dating diva Mariah Carey.  They married in 2008 but it didn't stand the test of time

14 Jennifer Aniston and Paul Rudd

Image source Getty ImagesJennifer Aniston and Paul Rudd have starred in loads of movies together and there has always been obvious chemistry between them.  They dismissed rumours they were dating although, during the filming of 'The Object Of My Affection', they did decide to take their friendship to a romantic level.  They didn't gel in the way they hoped so went back to being friends.

15. Leonardo DiCaprio and Gisele Bündchen

Image source Getty ImagesBefore marrying Tom Brady, Gisele Bündchen dated Leonardo DiCaprio.  The two of them were together for 5 years before splitting up in 2005.  Gisele commented, 'We were just not meant to be boyfriend and girlfriend, but I respect him enormously and I wish him nothing but the best.'

16. Justin Timberlake and Fergie

Image source Getty ImagesBack in 2003, Justin and Black Eyed Peas vocalist, Fergie, collaborated on 'Where is the Love?' Looks like the love was found in their hearts as they became a couple.  It was never intended to be serious and they separated a few months later, still remaining good pals!

17. Joaquin Phoenix and Liv Tyler

Image source Getty ImagesLiv Tyler and Joaquin Phoenix were only 18 when they started dating.  When they split up, aged 21, Liv stayed close to his sisters as she thought of them as her family.  The pair are still close but only in the platonic sense and always support each other through their respective movies

18. Josh Hutcherson and Vanessa Hudgens

Image source Getty ImagesAfter splitting with the gorgeous Zac Efron (why would anyone leave him), Vanessa began dating her 'Journey 2: The Mysterious Island' co star, Josh Hutcherson.  It didn't last very long after they realised they were better suited as friends rather than lovers.  They have stayed friends up to now.

19. Matt Damon and Winona Ryder

Image source Getty ImagesBack in 1997, Gwyneth Paltrow introduced Matt Damon to Winona Ryder (Gwyneth was  dating Damon's best friend at the time, Ben Affleck).  After hitting it off, Damon and Ryder started dating and they attended the 2000 Golden Globes together. Damon was nominated for 'The Talented Mr Ripley along with Paltrow.  It didn't last but both still speak very highly of each other

20. Luke Wilson and Gwyneth Paltrow

Image source Getty ImagesThe Oscar winning actress may have recently got married in secret to Brad Falchuck but, long before then, she was with Luke Wilson.  They stayed together for only a year or so.  That was until she got swept of her feet by her first husband, Chris Martin (of Coldplay).

21. Madonna and Michael Jackson

Madonna totally confused the world when she brought Michael Jackson as her date to the 1991 Academy Awards. They were seen together on dinner dates and at parties.  Many said it was a publicity stunt but Madge and Michael insisted they had 'brought out the best in each other'.  Not sure what that means!

22. Miley Cyrus and Nick Jones

Image source Getty ImagesThe former Disney Channel stars dated in their teens and when they spit up, Miley was devastated.   She told reporters, 'At first I bawled for a month straight. I was so sad. I just went into this weird funk. And I dyed my hair black.' She went on to say that she discovered who she really was (can you give us a clue Miley?)

23. Sarah Jessica Parker and Michael J. Fox

Image source Getty ImagesThe 'Sex and the City' star used to date 'Back to the Future' actor, Michael J. Fox back in the 1980s.  Their photos were splashed all over the tabloids over the space of a year before they announced they had gone their separate ways.  Many thought it was a bit PR stunt but we will never know!

24. Natalie Portman and Jake Gyllenhaal

Image source Getty ImgesBack in 2006, Jake Gyllenhaal and Natalie Portman had a brief romance.   Although it didn't last long, their friendship survived and is as strong today as it was back then.  Even though it wasn't a reason for splitting up, Jake said he was frustrated that Natalie was a vegan and they couldn't go for a good steak!

25. Sarah Jessica Parker and Robert Downey Jr.

Image source Getty ImagesAfter dating Fox and before she married Matthew Broderick, Sarah Jessica Parker and Robert Downey Jr. were an item for 7 years.  The downfall of their relationship was his alcohol and drug abuse.  SJP gave her partner so many chances to get clean but gave up in the end

26. Jennifer Lopez and Diddy

After Jennifer Lopez's divorce from Ojani Noa in 1998, the singer dated Sean Combs who we recognise as Diddy.  Combs said J.Lo was one of the greatest loves of his life but that didn't stop him cheating on her.  Not that it matters any more to Jennifer as she is now ecstatically happy (so we are led to believe) with her now husband, Ben Affleck!

27. Kate Hudson and Alex Rodriguez

Image source Getty ImagesAfter divorcing Chris Robinson in 2009, Kate Hudson got together with A-Rod (J.Lo's ex).  Rodriguez wasn't as committed as Kate as he was still nursing his break-up from Madonna.  When she found out he was still contacting Maddy, she gave him his marching orders.

28. Alexis Bledel and Milo Ventimiglia

Image source Getty ImagesThe on-screen couple (aka Rory Gilmore and Jess Mariano) dated in real life - how cute. Their romance began in 2001, just one year after starring in 'Gilmore Girls'.  They talked about marriage but split up after 4 years as they said the romance started to fizzle out.

29. David Arquette and Drew Barrymore

Image source Getty ImagesThe brother and sister co-stars in 'Never Been Kissed' had a very different relationship off-camera and there was lots of kissing!  Barrymore denied the relationship had been going on a while but Arquette told Howard Stern that the two of them started dating  before they shot the movie.

30. Jenna Dewan and Justin Timberlake

Image source Getty ImagesJenna Dewan was one of the back-up dancers for Justin Timberlake and she confirmed that the two of them hooked up for a short time after his split from Britney Spears.  She said, 'We dated, not that long. We were like friends...that dated," she said. "I was not the rebound! I was very clear not to be [that]'.