The Celebrity Hookups You Had No Idea Were Happening

With all the commotion going on lately surrounding celebrity relationships and hookups there is one common theme; why do the celebrities date all the same people? They are in the position to go fro whoever they want but somehow always end up hooking up with someone that another person in the industry has been with. And that is when the drama starts.

Wait… What?!?

Wait… What?!?

On the contrary, there are some relationships and hookups between celebrities that the general public may not have been aware of. That is exactly what this list is going to reveal to you. Here are all the biggest celebrities you did not know about!

Bruno Mars and Rita Ora

We will kick off the list with one of the most prevalent hit makers today and a hottie who is signed to Jay Z’s Roc Nation label. That’s right, Bruno Mars and Rita Ora have indeed hooked up! Bruno was not always in the spotlight like he is today. There was a time when he was just a songwriter trying to make it to the bright lights.

Bruno Mars and Rita Ora

That is when he met the beautiful Rita and the two immediately connected and had chemistry. She admitted that “it was love at first sight, such a great experience.” They met in 2009 and although the fling ended in 2011, the two still care deeply for each other.

The Game and Khloé Kardashian

A few of the Kardashian sisters have a little reputation for sleeping around with the famous men of Hollywood. Granted, Kim is now married with two lovely children and Khloé spent a few of her prime years with former NBA star Lamar Odom, that does not erase our memory of what they did in the past.

The Game and Khloé Kardashian

Recently, on The Wendy Williams Show, rapper The Game was a special guest and Williams asked him which of the Kardashians has he hooked up with. When he was showed a picture of Khloe he responded with, “Ah, sometimes it gets late at night …” That is all the answer we needed.

Kid Cudi and Amanda Bynes

The Man on the Moon is usually quite secretive when it comes to his private life but in 2010 he released a song with lyrics that spilled the beans about his love life. “Wanna know about me and Amanda Bynes (Amanda please),” were the lyrics he rapped and after that everyone was wondering if the two were seeing each other.

Kid Cudi and Amanda Bynes

During that time period, Amanda would tweet cryptic tweets that were almost guaranteed to be about Kid Cudi. No one is sure how long the flame lasted but once it was over Amanda confirmed it by clearing up a tweet that was posted on her account calling Kid Cudi ugly. “My account was hacked, I didn’t call him ugly. He’s not ugly. He’s gorgeous and we dated. I loved him;),” she tweeted.

Amanda Seyfried and Ryan Phillippe

According to Amanda Seyfried, this was something that was not meant to be. The two had met at Kate Hudson’s Halloween party and probably had a little too much to drink before they decided to leave together. That is usually how it goes with hookups and relationships that don’t last long; they are birthed from liquor. This one was no different.

Amanda Seyfried and Ryan Phillippe

Ryan is 11 years older than Amanda which probably contributed to the splitting and why she said, “You know when two people shouldn’t be together from the get-go? That’s why (we split).” It lasted for a short seven months.

The Cyclist and the Twin

Lance Armstrong was once seen as the greatest cyclist in the world. He would always dominate the Tour de France in a stunning fashion and would just make it look easy. That is until he got caught for using PEDs (performance enhancement drugs) and his name was clouded in shame.

The Cyclist and the Twin

This hookup happened after he broke it off with Sheryl Crow and the public was there for it as well. There were witnesses that saw Lance and Ashley displaying a lot of PDA including making out a bar in New York City. After those reports came out, the two were hardly seen with each other again.

Tom Cruise and Cher

This hookup may seem impossible but isn’t that what Tom Cruise is known for? Tom was just starting to flourish in his career when this unlikely match happened in the ’80s. Cher claimed that she was goo-goo crazy over him but Tom hardly ever talks about the time two spent together.

Tom Cruise and Cher

That led many to believe it was just for publicity but something does not just become nothing overnight meaning there had to be some type of flame there. If it was indeed just for publicity, then Tom was just another notch added to her belt. The same can be said for Tom.

Drake and Kat Dennings

Drake (who will appear again this list, surprise surprise) has been with his fair share of women from Hollywood. The Degrassi star started from the bottom and made it to the top of the food chain when it comes to seeing women. He most notably has been with Serena Williams and Rihanna but this one is rather unknown.

Drake and Kat Dennings

While he was on the Ellen show, he told Ellen, “I just always had a huge crush on Kat Dennings and she was kind enough one night to oblige me and we went out for dinner.” Now if Drake is as smooth as he thinks he is, then what do you think happened after dinner?

Kim Kardashian and Nick Lachey

We get it, Kim Kardashian is attractive and can use her superpowers to lock up any guy she wants. This hookup happened six months after Nick Lachey had broke things off with Jessica Simpson. And obviously it did not last but the phenomenon that happened with them is worth noting.

Kim Kardashian and Nick Lachey

Nick claims that the Kardashian used him to up her fame. “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,” he continued, laughing. You can’t put that past her with her history, can you?

Amanda Bynes and Seth MacFarlane

Yet again, Amanda Bynes finds her way on the list. This time not with an up and down musician but with a funny guy that won’t hesitate to make fun of her on his animated TV show. The man behind Family Guy and Bynes met in 2008 but they never confirmed that their relationship was a thing.

Amanda Bynes and Seth MacFarlane

One night at a party, however, Seth did refer to Bynes as his date to a reporter. They were even seen leaving that same party together. That is probably a couple that many did not see coming and we are assuming did not last too long.

Ashton and Rihanna

Rihanna is not one to be coy about her free spirit. She wears clothing that exposes intimate parts of her body and does so gladly. That is why Rihanna is so beloved by her fans; she does not care at all and it adds to her attractiveness. In 2012, she decided to make a late night visit to see a certain someone.

Ashton and Rihanna

On March 20, 2012, Rihanna was seen going to Ashton’s home that was for sale in the late night hours. She got there around midnight and did not leave until four in the morning. Rihanna has told friends that he is funny and cute.

Natalie Portman and Moby

Moby referred to her as every nerd’s dream girl. That is one way to define the beautiful Natalie Portman who is Harvard educated and currently married to Benjamin Millepied. The fling occurred in 2008 and Moby gave insights to it in a detailed interview.

Natalie Portman and Moby

You know someone has a crush on a person when they answer questions about them with great precision. He jokingly said, “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.”

Kristen Bell and Matthew Morrison

This hookup would have remained unknown if Kristen Bell did not reveal that the two went to college together. When you are in college there are either one of two types of hookups. The first one is the kind that is similar to one night stands but then turn into friends with benefits until the two of you get sick of it. The other one is something that turns into a lifelong partnership.

Kristen Bell and Matthew Morrison

These two had the former it looks like. “I actually went to college with Matty Morrison,” Kristen revealed in 2010. “We actually dated very briefly.” Hopefully, he did not have strong feelings for her.

Madonna and Tupac

This is probably one of the most interesting hookups on the list! Three years before Tupac’s death, he and Madonna were dating. They met for the first time in 1993 at the Soul Train Awards in Los Angeles after Rosie Perez introduced them. She had appeared one night on David Letterman and she says she was in a gangsta mindset because of one person.

Madonna and Tupac

“I was mad at [David Letterman] when I said the [expletive]-word a lot,” she told David Stern. “I was in a weird mood that day. I was dating Tupac Shakur at the time and the thing is, he got me all riled up about life in general.” He has that effect on people.

Jaden Smith and Kylie Jenner

The son of Will Smith pulled this one out of his bag when he nabbed Kylie Jenner. Before she got serious with rapper Tyga, apparently Kylie and Jaden were hooking up around London and Los Angeles. The two were reportedly and still are pretty great friends even as they were hooking up.

Kylie

They were young and one year apart when this was going on so when Jaden was asked about it, his answers seemed very elementary. “I was in L.A., we were all hanging out. Then I went to New York and she came too, then she came here [to London] and surprised me, so that’s pretty baller,” Jaden said.

Brad Pitt and Christina Applegate

In a time long before Brad Pitt and Angelina Jolie were even thought of, Pitt and Christina Applegate were a thing. This was in the late ’80s, well before Pitt was the household name that he is today and this was one he got to experience how much trickery is involved in Hollywood through a woman.

Brad Pitt and Christina Applegate

Applegate pulled a fast one over his head when she talked about a past moment that happened between them. “We were just part of this group of people that hung out and we decided to sort of cross the friend line,” she revealed. “We went to the MTV Awards and I ditched him! I left with somebody else.”

Drake and Tatyana Ali

Just how we mentioned earlier how Kid Cudi named dropped a woman in one of his songs which made people begin to speculate, Drake did the same thing. The woman he chose to name drop was none other than the former Fresh Prince of Bel-Air actress, Tatyana Ali.

Drake and Tatyana Ali

The lyrics go like this, “The fresh prince, just had dinner with Tatyana, no lie. All these ’90s fantasies on my mind.” Ali was on The Wendy Williams Show and said she would star in a reality show about Drake that would “Make him realize we’re meant to be together.” Sounds like more than a hookup was brewing there.

Justin Timberlake and Fergie

This hookup is a bit odd for one huge reason. Ordinarily, you would be thinking that this was a good match for a hookup. These two happened way back before the Black Eyed Peas when Fergie was in the Wild Orchid. Wild Orchid happened to open some shows up for NSYNC and that is how the two met.

Justin Timberlake and Fergie

Now here is the weird part. Are you ready? During his NSYNC days, Justin was a young boy scorching the music scene. It wasn’t until his first solo album that he became 21 years old. At the time he and Fergie were seeing each other, he was only 16 and Fergie was 23! This isn’t the Netherlands, the legal age is 18 Fergie!

Jay Z and Rosario Dawson

We are all aware of Jay Z and Queen Bey being an item for the past decade now, but about before he ran into the queen? In his songs he raps about taking down many women, not loving them and then leaving. It appears the queen made him change that tune.

Jay Z and Rosario Dawson

However, there was one woman on his list that he did stay attached too (and thank you because we wouldn’t have hot songs like Deja Vu!). This woman was Rosario Dawson. He has a song called “Lost Ones” where he addresses moving on from a woman so she could be all that she could be and many think it was about her.

Kelly Preston and Charlie Sheen

Before Kelly Preston caught John Travolta’s Saturday night fever, she had more than her fair share of bad boys. Her dating history is littered with bachelors, including heartthrob George Clooney. The real shocker here is that anyone could ever let George Clooney (or their pet pig which George kept after the split) go. Even more surprising is that Kelly was once engaged to Charlie Sheen.

Kelly Preston and Charlie Sheen

The engagement didn’t last very long which is not too surprising considering Charlie Sheen’s track record. They broke after Charlie Sheen accidentally shot his betrothed in the arm when a gun he had in the pocket of his pants fell out and discharged.

Mickey Rourke and Evan Rachel Wood

This relationship definitely has the “ick” factor. Mickey Rourke and Evan Rachel Wood hooked up after being cast as father and daughter in the 2008 film “The Wrestler.” Not exactly an on-screen romance, yet somehow the father-daughter relationship set off sparks in spite of a 35 year age differences.

Mickey Rourke and Evan Rachel Wood

Evan, who had just broken up with Marilyn Manson, claimed that the two were just friends, although eyewitnesses at a SAG afterparty saw the pair locking lips outside the Four Seasons Hotel in Los Angeles. Evan Rachel Wood continued to deny the relationship, though, saying “Spread the word—I’m not dating Mickey Rourke.

Roger Ebert and Oprah Winfrey

This one sounds like such an unlikely coupling that it couldn’t possibly be true, but it is. Back in the 80s, when Oprah Winfrey was just getting her start, she got involved with film critic Roger Ebert. The two had been friends for a long time when the relationship turned into…more.

Roger Ebert and Oprah Winfrey

Ebert convinced Oprah to syndicate her talkshow, catapulting her into superstardom. Without Roger Ebert, Oprah may not have turned into the legendary icon she is today. The relationship didn’t last long, and Roger Ebert married trial attorney Charlie Hammelsmith a few years later and passed away in 2013.

Brooke Shields and Michael Jackson

According to Brooke Shields, she met the iconic singer when she was only 13 years old. Years later, the two had a brief relationship. She said that Jackson asked her to marry him several times, but their relationship was not to be. Michael Jackson said about Shields, “That was one of the loves of my life. I think she loved me as much as I loved her, you know? We dated a lot. We, we went out a lot. Her pictures were all over my wall, my mirror, everything.”

Brooke Shields and Michael Jackson

Brooke Shields gave a touching eulogy at Jackson’s 2009 funeral, saying, “Thinking back to when we met and the many times that we spent together and whenever we were out together, there would be a caption of some kind, and the caption usually said something like ‘an odd couple’ or ‘an unlikely pair,’ but to us it was the most natural and easiest of friendships.”

Rosie Perez and Tupac

Now here is a relationship that is shrouded in mystery. Prior to Tupac’s untimely and tragic death, the rapper was allegedly involved with actress Rosie Perez. The two were seen together throughout the 90s and looked to be very close—way too close for a couple who claimed to be just friends.

Rosie Perez and Tupac

Rosie Perez, however, denies the relationship, claiming that she was never romantically involved with Tupac. Still, it is is pretty hard to ignore the evidence, like the fact that at the Soul Train Awards in 1993 the two were seen holding hands and staying quite close to each other.

Anne Heche and Steve Martin

Anne Heche is another kooky celebrity known for strange antics (such as looking for a spaceship in Fresno). She is also infamous for her dating choices. She once dated Ellen DeGeneres and had something of a nervous breakdown after the pair split up, getting married — some say on the rebound — not too long afterwards.

Anne Heche and Steve Martin

But before all of that happened, Anne Heche had an ill-fated love affair with comedian and actor Steve Martin. If that sounds like a strange pairing, that’s because it is, and also probably the main reason the relationship did not last. The two were together from 1993 to 1995.

Nicolas Cage and Brooke Shields

Brooke Shields strikes again! In addition to her fling with Michael Jackson, Brooke Shields had a quick affair with Nicolas Cage in the 1980s. This relationship happened when Cage was still building a name and reputation for himself and hadn’t become quite the tabloid and internet forum punchline that he is today, so maybe the relationship wasn’t that far fetched.

Nicolas Cage and Brooke Shields

The relationship was really short and the pair soon went their separate ways, but not before they attended the premiere of Moonstruck together. The two don’t seem to miss each other too much, both of them getting married to other people later on.

Edward Norton and Courtney Love

The relationships keep getting weirder and weirder. When people think of Courtney Love, they don’t really picture her with a nice, normal guy like Edward Norton. Love was previously attached to brooding musician Kurt Cobain, who totally seems like more her type. The relationship was Love’s first serious relationship after Cobain passed away.

Edward Norton and Courtney Love

Courtney Love met Edward Norton on the set of The People Vs. Larry Flynt in 1996, revealing Love’s unexpected acting chops. She won a Globe for her role in the film and also struck up a romance with her co-star. The relationship didn’t end well, but Courtney soon moved on.

Steve Coogan and Courtney Love

After her split with Edward Norton, Courtney Love moved on to comedian Steve Coogan. Coogan was a bit more her type, but the relationship quickly devolved into the kind of chaos that you would expect from Courtney Love. After the couple split up in 2004, Courtney did her best to ruin her ex’s reputation.

Steve Coogan and Courtney Love

A year after the split, Love claimed that she hadn’t slept with anyone since they broke up and that Coogan was the father of her child. She also blamed Steve Coogan for Owen Wilson’s drug problem and for his overdose, and attributed Coogan’s success to her.

Ryan Gosling and Sandra Bullock

Remember that movie where Sandra Bullock fell in love with a much younger man? Well that really happened, but with a different Ryan! Ryan Reynolds and Sandra Bullock had an on-screen romance in The Proposal, but a few years before that movie was filmed, Sandra fell for a different actor named Ryan.

Ryan Gosling and Sandra Bullock

The actress dated Ryan Gosling in 2002. Hugh Grant made fun of his friend’s relationship with a man 16 years her junior, calling Ryan “The Child.” Sadly, this relationship did not work out, although they parted on good terms. Ryan calls Sandra Bullock and Rachel McAdams as “the best girlfriends ever.”

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 has maybe just blocked from their minds because of the overwhelming weirdness of it.

Tila Tequila and Billy Corgan

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 that the earth is round, claiming that it is actually flat. The real question is what in the world was going on in Billy Corgan’s mind?

Jessica Simpson and Billy Corgan

Billy Corgan, like so many misguided men who came before him and will follow after him, has had more than his fair share of ill-advised relationships. In addition to his absolutely confounding fling with Tila Tequila, the musician has also been linked with Courtney Love (a match which, considering the history of both celebrities, almost makes sense).

Jessica Simpson and Billy Corgan

But perhaps the weirdest relationship Billy Corgan has had was a short-lived affair with Jessica Simpson. There’s a lot of debate over why the pair split up. Maybe he just got tired of explaining the difference between chicken and tuna to his girlfriend.

Tom Cruise and Sofia Vergara

Of course, the problem could simply be with Tom Cruise himself. He may be a gifted actor and quite the attractive star, but one person cannot possibly be that perfect. Long after his ill-fated fling with Cher and before he started dating Katie Holmes in 2007, Tom Cruise was head over heels for Sofia Vergara.

Tom Cruise and Sofia Vergara

The two were introduced by Will Smith and Cruise said that he wanted to marry Sofie. The two made quite the attractive couple, but the relationship was far from perfect. Apparently Sofie dumped Tom because he insisted that if they got married she would have to convert to Scientology.

Teri Hatcher and Michael Bolton

If you were even aware that this relationship had ever existed, you’ve probably forgotten about it by now. The actress and singer dated briefly in 90s after Teri Hatcher appeared in the music video for “Missing You Now.”

Teri Hatcher and Michael Bolton

The two broke up and went on to become mega-famous celebrities. Michael Bolton later dated actress Nicolette Sheridan, which reportedly made for some tense moments on the set of Desperate Housewives. Who wants to star on a show with the woman your ex-boyfriend dated after you broke up? Rumor has it that the other cast members of the hit television show weren’t too fond of Sheridan, either.

John Stamos and Marlee Matlin

This relationship happened in 1989, just when John Stamos was hitting international heartthrob status for his role on Full House. Who didn’t have a crush on Uncle Jesse? It turns out that actress Marlee Matlin was one of the countless people all over the world who had a thing for John Stamos—and who could blame her?

John Stamos and Marlee Matlin

The two got together after Marlee broke up with her co-star from Children of a Lesser God, William Hurt. Sadly, the relationship did not last very long; they spent a few months hitting up red carpet events before the two broke up and Stamos was back on the market reigniting the hopes of millions of smitten fans.

Lea Michelle and Matthew Morrison

Matthew Morrison has that sort of low-key appeal that makes him an instant woman magnet. After dating Kristen Bell, he had a brief relationship with fellow Broadway star, Lea Michelle. This shocked a lot of people when Lea spoke about the relationship in her book Brunette Ambition.

Lea Michelle and Matthew Morrison

The two might have had a student-teacher relationship on the musical TV show Glee, but in real life Matthew is only eight years older than the singer and actress. The two are still friends, but their on-screen chemistry on the show was pretty clear, especially in the episode where Lea’ character, Rachel Berry, has a huge crush on Matthew’s character, Mr. Schuester.

Matt Damon and Winona Ryder

Oh, Matt and Winona. This couple was the go-to Hollywood “It” couple for a brief time at the turn of the millennium. They broke up when Winona Ryder’s biggest problems were negotiating her salary for her next blockbuster film. A couple years later, she would be caught up in a shoplifting scandal and “Free Winona” t-shirts would be spotted in high schools everywhere.

Matt Damon and Winona Ryder

Alas, this pretty pair was not to be. After their two year relationship came to a screeching halt, Matt Damon got together with Odessa Whitmire, who had previously been a personal assistant to Billy Bob Thornton and Ben Affleck.

David Duchovny and Winona Ryder

The Winona Ryder of the 1990s was very different from the Winona Ryder of the early 2000s. Long before her breakup with Matt Damon and her shoplifting fiasco, she had a brief fling with David Duchovny. If you’re having trouble picturing the pair together, you’re not the only one.

David Duchovny and Winona Ryder

The relationship didn’t last long, starting and ending in 1996. David Duchovny, however, continues to deny the relationship. The notoriously private actor said that the two never actually dated and that they were “just friends.” Sure, David. We’ve heard that line before. David Duchovny would later get together with actress Téa Leoni.

Ted Danson and Whoopi Goldberg

There really are just no words to explain how truly strange and bizarre this relationship was. Whoopi Goldberg is a phenomenal singer and actress who deserves the best, and the best is definitely not an adulterous Ted Danson.

Ted Danson and Whoopi Goldberg

Ted Danson, who was married to Casey Coates at the time, just could not resist the allure of the Sister Act actress. He cheated on his spouse with Whoopi which led to their inevitable divorce in which Casey was awarded a $30 million settlement because of Ted’s philandering ways. Whoopi wasn’t having any of his nonsense either, and Ted was left on his own.

Now You’re in the Know

Are you surprised now? All these hookups going on under your nose that the media kept from you or you simply did not know about have just been delivered to you on a silver platter. Could you even imagine what Kid Cudi and Amanda Bynes might have been like? Or what about Kristen Bell and Matthew Morrison, so many blank spaces that need to be filled in.

Now You’re in the Know

One thing we do know is that these hookups were not meant to last and for the most part just a creation of lust. Many of the other halves are in committed relationships now with kids!