Celebrities are just like us: they have long histories of failed romances, friends-with-benefits and late night booty calls. Many celebrities have had flings you might have totally forgotten, or never even knew about. Some of the celebrity relationships in this gallery will have you shaking your head yes, feeling confused, or saying “oh no!”
Sandra Bullock and Ryan Gosling
Sandra Bullock fell for Ryan Gosling on the set of their film Murder by Numbers. Never mind that she was 16 years older than the young actor. Hugh Grant thought the match was hilarious, and called Gosling “The Child.” The romance didn’t last and apparently, Gosling broke the actress’ heart. Sources close to Bullock say that for awhile, she was was terrified of running into Ryan because she still had feelings for him. Gosling, to his credit, has named her the “best girlfriend ever.”
Rosie Perez and Tupac
We don’t know if actress Rosie Perez really dated Tupac, but we certainly have clues that the two had a fling! For one, there’s a photo of them at the Soul Train Awards in 1993; this is the same event where Perez says she introduced Madonna to the rapper. Perez and Tupac met while they were both on tour in the 1990’s. Perez was working as a choreographer for Heavy D and Tupac was a dancer for Digital Underground. In an interview with XXL, the actress says that the hand holding was just as friends because her date canceled last minute.
Jessica Simpson and Billy Corgan
What is wrong with Smashing Pumpkins legend Billy Corgan? He’s had two weird relationships on this list. Corgan says that he was asked to work on Jessica Simpson’s reality show in 2010, and that was that. He’s disputed claims that they were together, and says that she “deserves loving.” He said “my goal is to love whoever I think is worth loving.” They called it quits in 2010.
Kim Kardashian and Nick Lachey
Are you surprised that Nick Lachey says Kim “used him” to be famous? After all, look at the way she got famous from a certain sex tape. Nick Lachey dated Kim for a brief period after he separated from Jessica Simpson in 2006. He says the two went out on a date to the movies, and when they came outside, there were 30 photographers waiting. In her book, Kardashian Konfidential, Kim says that her fame began with that moment because the “paparazzi was curious about who he was with.”
Christina Applegate and Brad Pitt
Before Angelina Jolie and before Jennifer Aniston, Brad Pitt dated Christina Applegate, albeit briefly. Literally one date when she was 18. Applegate was in the 2nd season of Married with Children, and took Pitt to the MTV Music Awards. She ditched Pitt for a mystery man, and she’s never revealed his identity. We don’t think Pitt was hurting for dates, however.
Whoopi Goldberg and Ted Danson
Ted Danson was married to Casey Coates when he made the movie Made in America with co-star Whoopi Goldberg. While on set, Danson grew close to Goldberg, and the two began a romantic relationship in April, 1992. Danson had been married to Coates since 1977, but his thing with Goldberg ended his marriage. He moved out of the family home and into a new Malibu bachelor pad. The relationship with the Sister Act didn’t last either, and it was over by November 1993. Danson ended up moving on to marry Mary Steenburgen in 1995. For what it’s worth, tabloids have reported that Whoopi has a “grudge” against Ted’s wife.
Kat Dennings and Drake
Drake and Kat Dennings’ relationship wasn’t nearly as high-profile as his fling with Rihanna or Serena Williams. During an appearance on Ellen, the rapper said that he’s “always had a thing” for Dennings. Dennings actually went on a sushi date with Drake, and well, that wasn’t perceived well by Twitter. Drake’s Twitter followers went after Dennings, and attacked her for the date. Dennings said that she was overwhelmed by the amount of security Drake had for the night out, so clearly, this didn’t go very far.
Amanda Bynes and Kid Cudi
Kid Cudi was mum about his relationship with Amanda Bynes, but finally mentioned it in the song “Cudderisback.” The song’s lyrics include “Wanna know about me and Amanda Bynes (Amanda please),” so it was clear the two had something going on. Bynes’ cryptic tweets about a mystery man, posted during the same time they were rumoured to be dating, was another giveaway. Later, after posting tweets calling him ugly, she cleared it up, saying she was hacked, and “I loved him.”
Justin Timberlake and Fergie
The idea that Justin Timberlake and Fergie dated is strange enough. Crazier still when you consider Justin was just 16, and still with NSYNC, at the time of his tryst with Fergie. She was 23 and part of the all-female musical group Wild Orchid, which opened concerts for the pop superstars. Back then Fergie was known as Stacey Ferguson. The relationship didn’t last, and Timberlake was soon dating Britney Spears.
Rita Ora and Bruno Mars
Musicians dating musicians is common in the industry. But Rita Ora and Bruno Mars? Ora called it a “wonderful romance”, said it was love at first sight. “In 2008, I was 18 and starting out at Roc Nation. He was a struggling songwriter hired to write songs for me,” told German magazine Bravo. “I thought, ‘wow, that’s just the world’s greatest guy.'” The two split in 2011, with Ora turning her attention to Rob Kardashian.
Tupac and Madonna
Let’s go back to the 1990’s for this one. It was a time for grunge, acid-washed jeans and weird hookups like… Tupac, one of the world’s greatest rappers and… Madonna? Yes, the Queen of Pop dated Tupac for three years before his death in ’96. The couple reportedly met when Rosie Perez introduced them at the Soul Train Awards. Sounds like a SNL sketch, doesn’t it?
Tila Tequila and Billy Corgan
There’s just no good explanation for this one. The frontman for the Smashing Pumpkins had a brief fling with Tila Tequila that no one really remembers or maybe just blocked from their minds because of the overwhelming weirdness of it.
Yet the wacky matchup makes a weird sort of sense when you consider how kooky Tila Tequila is. We are talking about a girl who has talked about her support for Hitler. She also has denied the fact the earth is round, claiming it’s actually flat. The real question is what in the world was going on in Billy Corgan’s mind?
Oprah Winfrey and Roger Ebert
This isn’t a dating Mad Libs, this was a real couple. Roger Ebert once dated the Queen of TV, Oprah Winfrey. They apparently had two dates after being friends for a while and one thing led to another. Ebert said he “helped her get her start” by convincing her to syndicate her TV talk show, and now she is Oprah with a capital “O.” Oprah’s show even shared their history under the headline “Oprah and Roger Ebert’s Date with Destiny,” with the two talking about the experience. When Ebert died in 2013, Oprah was part of an all-star tribute to the beloved film critic.
Anne Heche and Steve Martin
Anne Heche didn’t just date Steve Martin for a few months, she did so for an entire year. She was only 24 and not ready for anything serious. As she told Larry King once: “I was compartments of me. I — that was not his fault. But I was compartments of Anne. I was not ready at 24 years old to be Mrs. Steve Martin. But I loved the relationship. But I wasn’t me at all. And in the meantime, I’m thinking I’m somebody else and dealing with the abuse of my life. And marriage, it just — it was not right.” The actress ended up leaving him, and the two didn’t remain friends.
The Game and Khloé Kardashian
Another Kardashian has been busy on the hookup circuit and we’re not talking about Kim! Khloe has a reputation for hooking up with NBA stars, marrying Lamar Odom, dating James Harden and Tristan Thompson. However, before she got into basketball players, Khloe dabbled with rappers. The Game was one of Khloe’s booty calls. When The Game visited the Wendy Williams show, she asked him just how many Kardashians he had hooked up with. He confirmed his situation with Khloe, saying, “Ah, sometimes it gets late at night …” That may even mean they are still getting it on in secret.
Kelly Preston and Charlie Sheen
Kelly Preston is with John Travolta now, but she was with someone else before that romance. Of course, we all knew about George Clooney, but what about Charlie “Tiger Blood” Sheen? Yes, the two dated and were even engaged! For years people believed that Sheen shot her accidentally in the arm, but in 2011, Preston tried to end that rumor (though it was reported in the NY Times in the 1980’s!). The story is that while in the bathroom, she picked up his pants and inside was a tiny revolver that fell out, hit the floor, and shot between her legs. The bullet hit the toilet bowl and she was hit with shrapnel. The engagement ended soon after that, but Preston calls him a “good person.”
Jay Z and Rosario Dawson
It’s hard to even remember a time when Jay Z was not with Beyonce, especially after the two were forever linked through their albums, Lemonade and 4:44. But believe it or not, he had a history before Queen Bey. His early songs discuss all the women he hooked up with, loving and leaving with impunity.
But Jay Z didn’t drop every woman like a hot potato despite his lyrics. He stuck with actress Rosario Dawson for quite awhile, and he even named her on his track “Lost Ones” where he raps about having to break up with a woman to allow her to spread her wings and fly. Sources say the song is about Dawson.
Tom Cruise and Cher
Okay, you may not remember this, but Tom Cruise hooked up with Cher. That’s right, these two weirdos got it on back in the early 1980s. According to Cher, she was totally into Cruise. Tom never talks about his past. Some people assume the brief relationship was just fake and engineered for publicity. However, Cher is adamant that what they had was actually real. Tom and Cher both went on to many other high profile significant others.
Nick Cannon and Kim Kardashian
Kim Kardashian has a lot of notches on her bedpost. Let’s look at one that got the least amount of attention. Funny man Nick Cannon dated Kim long before he married (and divorced) Mariah Carey and she married and divorced and remarried. Their relationship started just after Kim had become an unlikely star due to a sex tape with Ray J. “We talked about this tape, and she told me there was no tape,” Cannon said “If she might have been honest with me, I might have tried to hold her down.” At the time, Kim thought the tape was a liability. But once it was released, she embraced the fame and has never looked back.
Ashton Kutcher and Rihanna
Rihanna has had many boy toys during her career as the sexy pop star is a free spirit. Back in 2012, someone saw Rihanna heading over for a late night rendezvous with Ashton Kutcher. The songstress arrived around midnight on the night of March 20, and didn’t leave until 4:00 a.m. In other words, this was a classic booty call. The one-time fling sounds just like something out of an Ashton Kutcher movie.
Natalie Portman and Moby
Natalie Portman brings all the nerdy boys to the yard, like Darren Aronofsky and Moby. In fact, Moby even called her the dream girl of every nerd. Portman is now married to ballet dancer Benjamin Millepied, but back in 2008, she was still on the market. That’s when she dated Moby. He has fond memories of that time. “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.”
Nicolas Cage and Brooke Shields
Brooke Shields once had a fascinating dating life. (Purring “nothing separates me from my Calvins” didn’t hurt her cause). Michael Jackson was not her only unusual hookup. She also had a brief affair with Nicolas Cage in the 1980’s. Cage was still new to the acting game and was a virtual unknown, unlike the case today, when he’s sort of a joke on the Internet. Cage took Shields to the premiere of Moonstruck. His career took off, they broke off, and Shields went on to marry and divorce Andre Agassi before finding wedded bliss with Chris Henchy and having two children.
Amanda Bynes and Seth MacFarlane
Amanda Bynes strikes again! This time she went in the other direction, nabbing a funny man with a good reputation and several hot TV shows. The Family Guy creator first met Bynes in 2008 when she voiced “Anna” in the episode “Long John Peter”. Neither confirmed their relationship, until McFarlane cracked after a party, telling a reporter that Bynes was his girlfriend. The two were then seen leaving the party as a couple. The two have not discussed their relationship at all, so it was obviously short-lived.
Lance Armstrong and Ashley Olsen
Lance Armstrong used to be one of the most admired men in the world. He won the Tour de France seven times and defeated cancer. He was married and had three children. He started a cancer charity. He was squeaky clean. And then, his entire life collapsed. He divorced. He admitted to being a chronic user of PEDs (performance enhancement drugs) and his name was forever tarnished.
Armstrong wallowed in his bad reputation, dumping Sheryl Crow and then hooking up with – get ready – Ashley Olsen from Full House! Armstrong was then 36 years old, and the CEO of his foundation warned Armstrong that the age difference would be bad for his image. Armstrong reportedly responded “She’s twenty-one… F**k you.” Armstrong and Ashley carried on with public displays of affection in New York City. But the public reaction was so strong, the two deep-sixed their relationship.
Drake and Tatyana Ali
Whenever a rapper name drops on an album, it’s likely they either had a beef or a fling. Drake called out Tatyana Ali, who co-starred on the Fresh Prince of Bel-Air. His lyrics about Ali say: “The fresh prince, just had dinner with Tatyana, no lie. All these ’90s fantasies on my mind.” When Wendy Williams had Ali on her show, the actress said she would love to star in a reality show about Drake that would “Make him realize we’re meant to be together.” Ali obviously had quite a thing for the Canadian.
Matt Damon and Winona Ryder
If you grew up in the 1980’s, you might have made Winona Ryder and Matt Damon your “relationship goals” couple. They were both stars on the rise when they started walking the red carpet together. Ryder was the bigger star back then. They lasted for two years. After they broke up, Ryder dated several different rock stars: Pete Yorn, Conor Oberst, Page Hamilton, Dave Grohl, Dave Priner from Soul Asylum and Blake Bennet from Rilo Kiley. And her pre-rock star roster of boyfriends is legendary: David Duchovny, Brad Pitt, Christian Slater and Johnny Depp.
Amanda Seyfried and Ryan Phillippe
Amanda Seyfried is a newly married mother, but she had some high-profile flings in her past. One of them was Ryan Phillipe. Seyfried met Ryan in Hollywood at Kate Hudson’s Halloween party. The twosome got very sauced and then got saucy with each other. Ryan was a full 11 years older than Seyfried, so they didn’t necessarily have much in common. Still, their relationship lasted seven months. Seyfried now says it was wrong from the start. “You know when two people shouldn’t be together from the get-go? That’s why (we split).”