35 celebrity couples you definitely forgot about 🤯

Remember when Gossip Girl met real life?

shock celebrity couples

by Siam Goorwich |
Updated on

Think you know whose dated who in Hollywood? Think again...

Hollywood is an incestuous place. Ok, maybe incestuous is a bit strong, but Hollywood is basically like a massive high school, in that everyone has dated everyone else.

Think we're exaggerating? Then you need to take a look at this gallery of 35 celebrity couples we forgot ever dated.

From Nicole Kidman and Lenny Kravitz (yes, really) to Kim Kardashian and Nick Cannon, prepare for some serious WTF moments...

GALLERY: 35 celebrity couples we totally forgot about...

Gallery

35 celebrity couples we forgot about SLIDER

Jennifer Aniston and Owen Wilson1 of 44
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1. Jennifer Aniston and Owen Wilson

Jennifer and Owen dated for a short time in 2008 after filming Marley & Me together.

Sandra Bullock and Matthew Mcconaughey2 of 44
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2. Sandra Bullock and Matthew Mcconaughey

Sandra Bullock and Matthew Mcconaughey became a couple after starring in A Time To Kill together. Despite the fact they looked SUPER CUTE together with their matching glossy curls, their relationship lasted less than two years.

Seal and Tyra Banks3 of 44
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3. Seal and Tyra Banks

Before Seal married Heidi Klum and started throwing THE BEST Halloween parties of all time (seriously, if you don't know, check them out), he briefly dated model and 'smize' enthusiast, Tyra Banks.

Johnny Depp and Kate Moss4 of 44
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4. Johnny Depp and Kate Moss

We don't want to be dramatic, but Kate Moss and Johnny Depp were probably the hottest couple OF ALL TIME.

Johnny Depp and Kate Moss5 of 44
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Johnny Depp and Kate Moss

Seriously, just look at them. That hair! Those cheekbones! PHWOAR!

Johnny Depp and Kate Moss6 of 44
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Johnny Depp and Kate Moss

The couple met in 1994 - when Johnny was 31 and Kate was just 20 - and dated for four years and were reportedly even engaged.

Kirsten Dunst and Jake Gyllenhaal7 of 44
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5. Kirsten Dunst and Jake Gyllenhaal

Brace yourselves, ladies, for you're about to witness pictures of dreamboat Jake Gyllenhaal looking TOTALLY besotted with another woman. The woman in question is, of couse, Kirsten Dunst, who he dated from 2002 - 2004.

Kirsten Dunst and Jake Gyllenhaal8 of 44
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Kirsten Dunst and Jake Gyllenhaal

Look, here he is gently cupping her face as he stares adoringly into her eyes...

Kirsten Dunst and Jake Gyllenhaal9 of 44
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Kirsten Dunst and Jake Gyllenhaal

And here they are snogging each other's faces off in a doorway. JEALOUS!

Kate Bosworth and Orlando Bloom10 of 44
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6. Kate Bosworth and Orlando Bloom

Long before he went naked paddle boarding with Katy Perry, British actor Orlando Bloom dated super-chic actress Kate Bosworth.

Cindy Crawford and Richard Gere11 of 44
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7. Cindy Crawford and Richard Gere

Wow, these two REALLY looked great together. Just look at them! Cindy Crawford and Richard Gere first met in 1987 when Cindy was just 21, and wed four years later. Sadly their huge 17-year age gap proved fatal, and the couple divorced just four years later in 1995.

Sandra Bullock and Ryan Gosling12 of 44
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8. Sandra Bullock and Ryan Gosling

Yes, much to everyone's surprise, Ryan Gosling and Sandra Bullock were once a 'thing'. Briefly.

Alec Baldwin and Kim Basinger13 of 44
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9. Alec Baldwin and Kim Basinger

Kim Basinger and Alec Baldwin were married for nine years and have one child - Ireland Baldwin - together. Sadly, their relationship ended in a bitter divorce in 2002.

Blake Lively and Penn Badgley14 of 44
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10. Blake Lively and Penn Badgley

Long before Blake was ultimate #CoupleGoals with hubby Ryan Reynolds, she made Gossip Girl fans' dreams come true by dating her GG co-star Penn Badgley. Sadly the couple broke everyone's hearts by splitting up three years later, but we think we can all agree it was for the greater good.

Natalie Portman and Moby15 of 44
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11. Natalie Portman and Moby

Yes, Oscar winning actress Natalie Portman briefly dated the much-maligned musician (and fellow vegan), Moby. Strangely, the only image we could find of them was this one where they're posing with Questlove and Black Thought from The Roots and even more inexplicably, Natalie's holding a cake. GO FIGURE.

Whoopi Goldberg and Ted Danson16 of 44
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12. Whoopi Goldberg and Ted Danson

Whoopi Goldberg and Ted Danson's relationship may have been short (it only lasted about a year), but it had HUGE ramifications - mainly because Ted was married at the time and his affair with Whoopi resulted in his second divorce. Gulp.

Gwyneth Paltrow and Brad Pitt17 of 44
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13. Gwyneth Paltrow and Brad Pitt

Can we all just take a moment to remember just how great Gwyneth Paltrow and Brad Pitt were together. Look - they even had matching hair! The couple, who were together from 1994 - 1997 met when Gwynnie was just 24, and were even engaged. Talking about the relationship years later, Oscar winner Gwyneth admitted: "I f----- that up, Brad!" REGRETS!

Gwyneth Paltrow and Ben Affleck18 of 44
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14. Gwyneth Paltrow and Ben Affleck

Who do you possibly date if you've just broken up with Brad Pitt? Well, if you're Gwyneth Paltrow, that answer's Ben Affleck. The couple dated on and off till 2000.

Sienna Miller and Rhys Ifans19 of 44
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15. Sienna Miller and Rhys Ifans

Let's take a trip back to 2007, when Sienna Miller had everyone asking, 'WTF does SHE see in HIM?' when she began dating super-scruffy Welsh actor Rhys Ifans (yes, we know he's probably got a great personality, but COME ON!).

Kim Kardashian and Nick Cannon20 of 44
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16. Kim Kardashian and Nick Cannon

Back when Kim Kardashian was BFFs with Paris Hilton and still had most of her real face (circa 2006), she was doing the dirty with Nick Cannon - aka. Mariah Carey's baby daddy.

Kim Kardashian and Nick Cannon21 of 44
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Kim Kardashian and Nick Cannon

And look, here they are posing with a topless woman who's carrying a snake. Good times!

Ashton Kutcher and January Jones22 of 44
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17. Ashton Kutcher and January Jones

Before we all knew her as Betty Draper in Mad Men, January Jones dated Ashton Kutcher. The couple dated from 1998 - 2001, but sadly, despite the fact they look seriously happy in this snap, it turns out Ashton was a bit of a jerk. Talking to GQ in 2009, January admitted: "He was not supportive of my acting... He was like, 'I don't think you're going to be good at this."

Kiera Knightley and Jamie Dornan23 of 44
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18. Kiera Knightley and Jamie Dornan

Long before he was dark and brooding and Christian Grey, Jamie Dornan was the dark, brooding boyfriend of Kiera Knightley. Lucky girl!

Chris Evans and Jessica Biel24 of 44
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19. Chris Evans and Jessica Biel

Yes, Jessica Biel (who's now happily to married to Justin Timberlake) used to date Captain America! Sorry, we mean, Chris Evans. Who knew?

Madonna and Sean Penn25 of 44
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20. Madonna and Sean Penn

Madonna's dating history is long and varied - from legendary artist Jean Michel Basquiat to, er, Vanilla Ice - but let's take a minute to remember that her first husband was none other than Sean Penn. The couple were married from 1985 - 1989, and although they weren't suited in many many ways, they certainly looked great together.

Jennifer Lopez and Wesley Snipes26 of 44
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21. Jennifer Lopez and Wesley Snipes

J-Lo has had some hot, and seriously famous, O/H's (hiya Diddy, Marc Anthony, Ben Affleck!), but did you know she briefly dated actor Wesley Snipes in the mid-90s? No, neither did we!

Mila Kunis and Macaulay Culkin27 of 44
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22. Mila Kunis and Macaulay Culkin

And the award for the cutest celeb couple of all time is... Mila Kunis and Macaulay Culkin. Seriously, just look at them! We. Can't. Cope.

Winona Ryder and Matt Damon28 of 44
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23. Winona Ryder and Matt Damon

Winona Ryder and Matt Damon met in 1997 after being introduced by Gwyneth Paltrow (who was dating Matt's mate Ben Affleck at the time). The couple became official in 1998, but broke it off just two years later in 2000.

Owen Wilson and Sheryl Crow29 of 44
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24. Owen Wilson and Sheryl Crow

Owen Wilson dated All I Wanna Do singer Sheryl Crow from 1999 - 2001. Here they are having a red carpet snog which Sheryl doesn't look 100% comfortable with. Eek!

Courteney Cox and Michael Keaton30 of 44
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25. Courteney Cox and Michael Keaton

Courteney Cox and Michael Keaton dated for an impressive (in Hollywood terms, at least) six years. Following their split in 1995, Courteney said: "It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met." Awww!

Jennifer Aniston and Vince Vaughn31 of 44

26. Jennifer Aniston and Vince Vaughn

Remember when Jennifer Aniston dated Vince Vaughn? The couple started dating after filming The Break Up together (which was possibly a bad omen) because, as you can see from this snap of them not enjoying each other's company, it wasn't really #CoupleGoals

Ryan Reynolds  and Alanis Morissette32 of 44
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27. Ryan Reynolds and Alanis Morissette

Does Ryan Reynolds and Alanis Morisette strike anyone else as a bit of an odd coupling? Yes, we know they're both Canadian, but still. Anyway, the couple dated for five long years after meeting at Drew Barrymore's birthday party in 2002 (IMAGINE!), and were even engaged to be married.

and Alanis Morissette33 of 44
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and Alanis Morissette

Sadly they never made it down the aisle, but they did manage to get in A LOT of PDAs before splitting in 2007.

George Clooney and Lucy Liu34 of 44
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28. George Clooney and Lucy Liu

George Clooney's dated more gorgeous women than we've had hot dinners, but we were particularly into his short-lived fling with Charlie's Angels star Lucy Liu.

Johnny Depp and Kate Moss35 of 44
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29. Cameron Diaz and Jared Leto

Look at these cool kids! Yep, Cameron Diaz and Jared Leto dated from 1999 - 2003 and were reportedly even engaged. We think they looked pretty great together tbh.

Nicole Kidman and Lenny Kravitz36 of 44
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30. Nicole Kidman and Lenny Kravitz

Despite the fact that Nicole Kidman and Lenny Kravitz dated for two years (2003 - 2005) and were even engaged, the only photos we could find of the pair was this seriously awkward encounter with Nicole's hubby Keith Urban.

Nicole Kidman and Lenny Kravitz37 of 44
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Nicole Kidman and Lenny Kravitz

Like, REALLY awkward. Let go of her hand, Lenny!

Sarah Jessica Parker and Robert Downey Jr.38 of 44
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31. Sarah Jessica Parker and Robert Downey Jr.

Yes, that is Robert Downey Jr. And yes, he dated Sarah Jessica Parker - for an incredible seven years in fact! We love this snap of them looking seriously cute and gawky back in 1990!

Sarah Jessica Parker and Robert Downey Jr.39 of 44
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Sarah Jessica Parker and Robert Downey Jr.

And here they are at the London premiere of SJP's film LA Story shortly before their split in 1991.

Whitney Houston and Ray J40 of 44
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32. Whitney Houston and Ray J

We LOVED Whitney, but she really did have awful taste in men. At the time of her death the legendary singer was dating Ray J (of Kim Kardashian sex tape fame).

Cameron Diaz and Justin Timberlake41 of 44
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33. Cameron Diaz and Justin Timberlake

Cameron Diaz and Justin Timberlake began dating after meeting at the Nickelodeon Kids' Choice Awards in 2003 (proof that love can strike any time, any place). The couple dated for almost four years, and appeared to spend much of their relationship looking loved-up at sports events. Here they are staring lovingly into each other's eyes at a charity basket ball game...

Cameron Diaz and Justin Timberlake42 of 44
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Cameron Diaz and Justin Timberlake

And here they are having a cheeky snog at a Lakers game. As you do.

Jennifer Aniston and Tate Donovan43 of 44

34. Jennifer Aniston and Tate Donovan

Before Brad, Jennifer Aniston dated Tate Cooper- who you'll probably know as Jimmy Cooper, Marissa's hot dad in The O.C.

Tom Cruise and Penelope Cruz44 of 44
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35. Tom Cruise and Penelope Cruz

And finally, who can forget the time that Tom Cruise and Penelope Cruz began dating and everyone REALLY hoped they'd get married and double barrel their names #Mems

WATCH 10 of the most EXPLOSIVE celebrity breakups of 2019

How's this lot for a blast from the past? Special mentions go to Kate and Orlando, who destroyed our elfin dreams, and fresh faced Keira Knightly and Jamie Dornan, who we don't like to think had a 50 Shades-esque relationship.

And also - boho sex goddess Sienna Miller and Trainspotting's Rhys Ifans?! What?

And also HOW did Gwenny have two high profile relationships before the highest of them all with Coldplay's Chris Martin? Phew.

And it's not just these retro sleb couples that are continuing to blow our minds decades later - there's some seriously bizarre hook-ups from over the past 20 years that we're still bamboozled by.

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The most shocking celebrity breakups of the decade

Any sleb worth their salt will tell you that dating civilians just doesn't work - in fact, there's a successful Channel 4 series that proves it.

That's why when it comes to the romantic lives of the rich and famous, we've had some majorly odd pairings to obsess over. For every Brangelina (the world's most beautiful couple were too good to be true) and Posh n' Becks (the footballer and the popstar, natch), there's a truly bizarre tryst that we just did not see coming.

From American poster boy Channing Tatum hooking up with Brit pop-sensation (and the spitting image of his ex-wife) Jessie J, to the many weird and wonderful incarnations of Chloe Green's love life, check out the most shocking hook ups of the decade that definitely bare revisiting.

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