Surprising Celebrity Couples From The Past That You Totally Forgot Dated

Since celebrity couples come and go like the wind, it’s difficult to remember who’s been with who throughout the years. Seriously, who remembers that Tom Cruise used to date Cher?

Alas, some strange and crazy pairings have happened, and this list is about to expose them all!

Penelope Cruz And Matthew McConaughey

Lalo Yasky/WireImage
Lalo Yasky/WireImage

It might have been short-lived, but Academy Award-winning actors Penelope Cruz and Matthew McConaughey dated for about a year! The two first got together while starring together in the 2005 film Sahara.

From there, they had some fun but inevitably broke up in 2006 due to their busy work schedules.

Katie Holmes And Chris Klein

Jim Spellman/WireImage for United Artists
Jim Spellman/WireImage for United Artists

In the early 2000s, Katie Holmes and Chris Klein were both hot commodities. They were young actors starring in some of the biggest TV shows and movies of the time, including Dawson’s Creek and the American Pie franchise.

They were pretty much the “it couple” people forgot about in later years after Holmes left Klein for Tom Cruise, or so the rumors go.

Ashley Olsen And Lance Armstrong

pjimage (1)
Rabbani and Solimene Photography/WireImage; Mark Sagliocco/Getty Images
Rabbani and Solimene Photography/WireImage; Mark Sagliocco/Getty Images

In 2007, one of the most unexpected pairings sparked dating rumors. That year, Ashely Olsen was seen cozying up to cyclist Lance Armstrong! According to his book Cycle of Lies: The Fall of Lance Armstrong, more than one friend warned him against dating Ashley.

Apparently, they were worried the young actress was going to ruin his image.

Chris Evans And Jessica Biel

Jon Kopaloff/FilmMagic
Jon Kopaloff/FilmMagic

Since Jessica Biel has been married to Justin Timberlake for so long, it’s hard to imagine her with anyone else. Well, going back to 2001, she was attached to none other than Captain America, Chris Evans.

The two were very serious, dating for about five years and even discussing the possibility of getting married one day. Obviously, that didn’t wind up happening.

Tyra Banks And Seal

Seal with Girlfriend Tyra Banks
Mitchell Gerber/Corbis/VCG via Getty Images
Mitchell Gerber/Corbis/VCG via Getty Images

It seems as though Seal has a thing for supermodels. In 1996, he had a very lowkey and under-the-radar relationship with none other than America’s Next Top Model host Tyra Banks.

The two didn’t flaunt their relationship though and only made one carpet appearance as a couple to the Essence Awards.

Uma Thurman And Gary Oldman

Uma Thurman and Gary Oldman...
Robin Platzer/IMAGES/Getty Images
Robin Platzer/IMAGES/Getty Images

Throughout his life, Gary Oldman has had five wives. So, it might have slipped some people’s minds that he once dated and married none other than Uma Thurman. The two actors met on the set of the 1990 movie State of Grace.

Later that year, they said their vows and were married. Alas, things didn’t work out, and they broke up two years later.

Julie Bowen And David Spade

40th New York Film Festival - Screening of Punch-Drunk Love
Jim Spellman/WireImage
Jim Spellman/WireImage

Julie Brown might be known as the matriarch of the Dunphey family in Modern Family. But she shocked fans when it was leaked that she was dating none other than comedian David Spade. Crazy!

Their relationship lasted a year and, according to Bowen, Spade is a great person but a horrible boyfriend.

Tom Cruise And Cher

First Annual Entertainment Industry Foundation
MCaulfield/WireImage
MCaulfield/WireImage

With Top Gun and Risky Business, Tom Cruise was making a name for himself back in the 80s. What no one saw coming, though, was the then 23-year-old actor getting together with the one and only Cher.

The two superstars met at Madonna and Sean Penn’s wedding. From there, they had a short fling.

Kim Kardashian And Nick Lachey

2nd Annual Derby Spectacular Celebration
Joey Foley/WireImage
Joey Foley/WireImage

While Kim Kardashian and Nick Lachey weren’t necessarily a couple, the two did go on a date after the 98 Degrees singer’s split from Jessica Simpson. In 2006, the two went to the movies to see The Da Vinci Code.

According to Lachey, he’s fairly certain the only reason Kim went out with him was for publicity.

Rihanna And Travis Scott

pjimage (2)
Dominique Charriau/WireImage; Bertrand Rindoff Petroff/Getty Image
Dominique Charriau/WireImage; Bertrand Rindoff Petroff/Getty Image

When people think of Travis Scott, they most likely think of him being paired with Kylie Jenner. Well, in 2015, he was actually romantically involved with mega-star Rihanna. While the two never fully admitted to being a couple, there were some tell-tale signs.

First, the up-and-coming rapper called Rihanna his “muse.” They were also photographed together on numerous occasions.

Helen Mirren And Liam Neeson

GettyImages-906695122
Matt Crossick/PA Images via Getty Images
Matt Crossick/PA Images via Getty Images

One wild pairing that happened in the 80s was between actors Helen Mirren and Liam Neeson. The two met on the set of the 1981 adventure film Excalibur and, according to Neeson, he “was smitten.”

After dating for four years, Mirren decided it was time to let Neeson go. He was too far under her wing, and he needed to make it in Hollywood on his own two feet.

Minka Kelly And Donald Faison

Jon Kopaloff/FilmMagic
Jon Kopaloff/FilmMagic

Considering the other high-profile actor Minka Kelly dated (Chris Evans), it might be amazing to be reminded that she also had a fling with Scrubs star Donald Faison. The two began dating in 2005, but it didn’t last very long.

Two short years later, Minka and Donald decided to go their separate ways, calling it quits.

Nicole Kidman And Lenny Kravitz

Hollywood Film Awards - Green Room
Charley Gallay/Getty Images for dcp
Charley Gallay/Getty Images for dcp

There have been many strange and crazy pairings in Hollywood, but the relationship between actress Nicole Kidman and singer Lenny Kravitz is definitely close to the top of the list.

They began dating in 2003 but were extremely private about their relationship. Shockingly, they were even engaged to be married!

Macauley Culkin And Mila Kunis

2004 Park City - Motorola Lodge
Dimitrios Kambouris/WireImage
Dimitrios Kambouris/WireImage

In one of the most confusing and surprising Hollywood relationships comes Macauley Culkin and Mila Kunis. The two began dating in 2002, and fans didn’t really know how to react to seeing the That ’70s Show star with the “has been.”

They would up going their separate ways in 2011, remaining good friends.

Tom Holland And Zendaya

David M Benett/Dave Benett/WireImage
David M Benett/Dave Benett/WireImage

The relationship between Spider-Man co-stars Tom Holland and Zendaya was a long time coming. Since Homecoming, fans were speculating the two were a couple, but the two actors denied, denied, denied.

Finally, in 2021, pictures surfaced of Holland and the Euphoria actress getting cozy in one of their cars. There’s no denying a relationship after that!

Kate Hudson And Alex Rodriguez

pjimage (5)
Dave Hogan/Getty Images; Alexander Tamargo/WireImage
Dave Hogan/Getty Images; Alexander Tamargo/WireImage

Alex Rodriguez has dated many women in his time, most recently being Jennifer Lopez. But before the epic A-Rod and JLo break of 2021, he was romantically involved with actress Kate Hudson.

But their romance didn’t last. Seven months after the two were seen packing on the PDA at a Yankees baseball game in 2008, they were done.

Nicolas Cage And Patricia Arquette

“Beyond Rangoon” at the 48th Cannes Festival
Stephane Cardinale/Sygma via Getty Images
Stephane Cardinale/Sygma via Getty Images

Considering Nicolas Cage has been married five times, it might have slipped some people’s minds that he was once with actress Patricia Arquette. The two met back in 1987. During their first date, Cage proposed on the spot.

After making Cage do a “quest,” which included getting a black orchid and a Bob’s Big Boy statue, the two married in 1995. Alas, it didn’t last, and their divorce was finalized in 2001.

Alexis Bledel And Vincent Kartheiser

19th Annual Screen Actors Guild Awards - Arrivals
Jeff Vespa/WireImage)
Jeff Vespa/WireImage)

People were pretty shocked when Gilmore Girls sweetheart Alexis Bledel started dating Mad Man star Vincent Kartheiser. In fact, the two actors met on the set of the latter show back in 2012 and quickly fell in love.

The two were engaged the following year and were married in 2014. As of 2021, they are happily married with one son.

Sarah Jessica Parker And Robert Downey Jr.

Robert And Sarah
Darlene Hammond/Hulton Archive/Getty Images
Darlene Hammond/Hulton Archive/Getty Images

This little fact is about to blow some people’s minds! Sarah Jessica Parker and Robert Downey Jr. dated for a solid seven years throughout the 80s. That’s right! A young Carrie Bradshaw and Tony Stark were very much in love during that particular decade.

Parker wound up leaving RDJ solely because of his substance issues at the time.

Matthew McConaughey And Janet Jackson

44th Annual Grammy Awards - Backstage
Frank Micelotta/ImageDirect
Frank Micelotta/ImageDirect

Alright, alright, alright. So, as it turns out, actor Matthew McConaughey once went out with singer Janet Jackson. Talk about a shocking relationship that wasn’t really talked about or publicized!

Allegedly, after the two met at the Grammys, they hit it off and decided to go out for dinner. It didn’t really go any further than that.

Jeff Goldblum And Geena Davis

61st Annual Academy Awards - Arrivals
Ron Galella/Ron Galella Collection via Getty Images
Ron Galella/Ron Galella Collection via Getty Images

In 1985, the stars literally aligned, and Jeff Goldblum and Geena Davis met on the set of Transylvania 6-5000. While they were high-profile stars, the two kept their lips sealed when it came to anything about their love life.

Even so, the two wed in a Las Vegas ceremony in 1987. In 1991, they were both once again single.

Cindy Crawford And Richard Gere

Cindy Crawford And Richard Gere, Mr Jones Premiere
Dave Benett/Getty Images
Dave Benett/Getty Images

Supermodel Cindy Crawford was only 26-years-old when she married 46-year-old actor Richard Gere in 1991. According to her, the two were never just friends but hopped straight into their relationship, their very strange relationship.

While the public was a bit confused about the nature of their relationship, Crawford and Gere were married for four years.

Sophia Bush And Chad Michael Murray

House of Wax Los Angeles Premiere - Outside Arrivals
Jon Kopaloff/FilmMagic
Jon Kopaloff/FilmMagic

Sophia Bush and Chad Michael Murray met on the set of the hit teen soap opera One Tree Hill. Not long after the cameras began rolling, the two were engaged to be married. It was 2004.

Then, in one of the briefest turnarounds in Hollywood, the two actors divorced after five months. Oh, but wait, their story isn’t over. They continued to work on the show with one another until 2012!

Zooey Deschanel And Ben Gibbard

Los Angeles Premiere of
Gregg DeGuire/FilmMagic
Gregg DeGuire/FilmMagic

A lot of fans were shocked to learn that Indie film sweetheart Zooey Deschanel was dating the lead singer of Death Cab for Cutie, Ben Gibbard. But it wasn’t meant to last between the actress and soft rock singer.

The two were married in 2009 and, two years later, their divorce was finalized.

Alanis Morissette And Ryan Reynolds

2003 MTV Movie Awards - Arrivals
SGranitz/WireImage
SGranitz/WireImage

It’s kind of hard to forget the relationship between Alanis Morissette and Ryan Reynolds, considering that after the break-up, the singer went and wrote a ballad about the actor, “Torch.”

Even so, while their relationship wasn’t the biggest news in the world, as people thought it was inevitable, their 2007 break-up was headline news.

Michael Keaton And Courtney Cox

NBC's Annual Winter Press Tour All-Star Reception
Steve Granitz/WireImage
Steve Granitz/WireImage

Michael Keaton and Courtney Cox met after the Friends actor mentioned to a mutual acquaintance that she liked Keaton’s performance in Clean and Sober. The two had their first date at Cox’s house, and, just like that, the two pretty much fell in love.

After nearly six years together, they decided to go their separate ways.

Rashida Jones And Tobey Maguire

pjimage (6)
Karwai Tang/Getty Images; Donato Sardella/Getty Images for PSLA
Karwai Tang/Getty Images; Donato Sardella/Getty Images for PSLA

Considering neither of them was famous quite yet, Rashida Jones and Tobey Maguire’s relationship wasn’t exactly making headline news. But the two did, in fact, date from 1997 until 2000.

There was even a rumor floating around that, at one point in time, the two actors were engaged. But there is no proof.

Cameron Diaz And Matt Dillon

Steve Granitz/WireImage
Steve Granitz/WireImage

Since Cameron Diaz has lived a private life with her husband Benji Madden, it might come as a shock to remember she dated actor Matt Dillon for a solid three years! They were even together when they were cast in the comedy film There’s Something About Mary.

But, like their love onscreen, their real-life romance wasn’t meant to last. They broke up soon after the film came to a wrap.

Edward Norton And Salma Hayek

2003 Sundance Film Festival -
George Pimentel/WireImage
Ron Galella/Ron Galella Collection via Getty Images

One celebrity couple people might have forgotten about is Edward Norton and Salma Hayek. The two actors began dating in 1999 after being set up by their mutual chiropractor, of all people!

In 2002, they starred together in Frida, a film that earned Hayek an Academy nomination. But, one year later, the two had gone their separate ways.

Brad Pitt And Christina Applegate

Amnesty International Event - 1988
Barry King/WireImage
Barry King/WireImage

Yes, Brad Pitt’s most high-profile relationships might be with Jennifer Aniston and Angelina Jolie, but he also dated actress Christina Applegate once upon a time. The two had a very brief relationship in the ’80s.

So brief, in fact, that a lot of people forget the two were ever together!