15 Celebrity Duos You Had No Idea Actually Hooked Up In Real Life

It gains more attention than a famous death. It has more people talking than a political scandal. It’s even bigger than a world war. Yes, we’re talking about celebrity couples. Famous celebrity relationships are one of the world’s greatest obsessions. The media, fans, critics, and scientists spend countless hours dissecting the allure of celeb couples. Since the beginning of the term “celebrity” status, the lifestyle and love lives of the rich and famous have been on public radar. Celeb couples that have been on the forefront of the tabloid scrutiny include Ben Affleck & Jennifer Lopez, Brad Pitt & Angelina Jolie, and Kim Kardashian & Kanye West. Everything from their vacations, anniversaries, fights, and breakups are often stealing the attention of generations. It seems that people just can’t get enough of these world famous couples.

There are several famous celebrity couples that didn’t get the attention some others have received. Perhaps, some couples are better at keeping a secret or maybe they just didn’t generate any interest. It might be quite shocking to find out that some of these couples even existed. Many couples seem like odd pairings and others appeared to be the perfect match but didn’t work out. Regardless, these famous duos somehow managed to fly under the radar. They quietly started dating and broke up without anyone even noticing a thing. Many of these celebs have moved on or are even married to an even more famous person. However, the past relationships are still very important. Here is a look at 15 celebrity duos you had no idea actually hooked up in real life.

15. Shia LaBeouf & Hilary Duff/ Shia LaBeouf & Rihanna

Shia LaBeouf and Hilary Duff had a very short and terrible date. That is the main reason this couple was able to keep their very short-term relationship a secret. Shia is best-known for his roles in Holes, Transformers, and Nymphomaniac. Hilary Duff starred in the popular kids sitcom Lizzie Mcguire. Shia has really got around Hollywood, so inevitably, he’d hook up with Hilary. They went on a date and it was so bad they never tried it again. They had dinner at a sushi restaurant and according to Shia, “Probably the worst date either of us has ever had.”

However, that wasn’t Shia’s only surprising relationship. In 2007, he dated musician Rihanna before either one was world famous. This didn’t work out for them either and they just didn’t click. Shia said about hooking up with Rihanna, “It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”

14. Kim Kardashian & Nick Lachey

Kim Kardashian and Nick Lachey have both dated just about everyone in Hollywood. They even crossed paths at one point. Kim Kardashian has been in several high profile relationships. She made a private video with Ray J, married Kris Humphries for 72 days, and is currently married to Kanye West. She also stars in the reality series Keeping Up with the Kardashians. Nick Lachey is no slouch as he was married to pop star Jessica Simpson, which was documented in the reality series Newlyweds: Nick & Jessica. Nick and Kim briefly dated after his divorce from Jessica. They were a very short-term couple as they dated for only one week in 2006. However, Lachey believes she was just using him and just tipped off photographers. Nick once said, “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.”

13. Lance Armstrong & Ashley Olsen

Both Lance Armstrong and Ashley Olsen are no strangers to being under the intense spotlight. There was a time when both names were often in the headlines for separate reasons. This may be why their relationship was so low key and even a surprise to some. Ashley Olsen played the role of Michelle Tanner along with her twin sister, Mary-Kate, in the sitcom Full House. Ashley has since retired from acting to focus on her career as a fashion designer. Lance Armstrong is a former professional cyclist that won seven consecutive Tour de France titles. He was banned from the sport and stripped of his titles after a doping scandal ended his career. In 2007, Lance and Ashley had a very brief relationship. Despite the 15-year age difference, they were extremely comfortable with each other. In fact, the duo was seen “making out” at a New York hotel bar. However, their relationship was short and came to a quiet end.

12. Britney Spears & Colin Farrell

Colin Farrell and Britney Spears pretty much both dated every celeb there is to date. So obviously, at some point, they had to date each other because nobody else was left. The only problem with that is Britney denies dating Farrell. On the other hand, Colin can’t wait to tell people about their short-lived romance. The controversial “princess of pop” is one of the best-selling solo artists of all time. She has released several popular singles, including “Oops I Did It Again,” “Toxic,” and “Womanizer.” Colin Farrell is known for his unapologetic bad boy image and his roles in Phone Booth, The Lobster, and Fantastic Beasts and Where to Find Them. In 2002, it was speculated that Farrell and Spears were an item. However, she denied all rumors that suggest they were together romantically. Apparently, not too long after her denial, Colin sent her a t-shirt that read, “I slept with Colin Farrell and all I got was this lousy t-shirt.”

11. Simon Cowell & Carmen Electra

The term “odd couple” doesn’t seem strong enough to describe the relationship between Simon Cowell and Carmen Electra. It might be surprising, but they really did date for a brief time. Carmen Electra is best-known for her mind-blowing appearances in Playboy magazine and for her role in Baywatch. Simon Cowell is well-known as the blunt and harsh judge on the reality shows American Idol, X-Factor, and America’s Got Talent. Simon and Carmen dated briefly from December 2012 to February 2013. Apparently, they were pretty crazy about each other in their short relationship. They were once spotted together enjoying a hearty meal at a West Hollywood restaurant. Seems like just an ordinary day in the lives of Simon and Carmen. However, according to an anonymous source that saw the couple, “They were really into each other. At one point, they were talking real close, and he leaned in and kissed her. They started making out.” However, things didn’t work out and both have moved on since.

10. Tom Cruise & Cher

Actor Tom Cruise once dated the “goddess of pop,” Cher, despite her being 16 years older than him. Early in his career, Tom really enjoyed dating older women. Tom Cruise has appeared in numerous memorable movies, such as Top Gun, The Firm, Jerry Maguire, and the Mission Impossible franchise. During her career, Cher has released groundbreaking albums, starred in critically acclaimed films, and won a plethora of awards. In 1987, Cher and Cruise dated in a short, but intense, relationship. At the time, Cher was at the height of her popularity and was one of the most famous celebs. Tom was just starting out and his career was about to take off. When discussing the relationship, Cher said, “I was crazy for him.” Regardless, the couple didn’t last very long and it soon came to an end. She also pointed out that he was a bit shy, but who can blame the guy when it comes to Cher?

9. Janet Jackson & Matthew McConaughey

Pop icon Janet Jackson once dated critically-acclaimed actor Matthew McConaughey. Well, at least that’s what Janet claims. Janet Jackson’s career has spanned several decades. She’s released universally praised singles, such as “Rhythm Nation,” “Nasty,” and “All For You.” Matthew McConaughey rose to fame with roles in Dazed and Confused, Magic Mike, and Dallas Buyers Club. According to Janet, they met at the 2002 Grammy Awards and, as she puts, had a short “fling.” There were rumors spreading that he was seen leaving her home shirtless. However, McConaughey denies that anything happened between them. When asked, he said, “I met her at the Grammy’s and found her to be a very sweet lady. We swapped some good music and she’s a dear lady. She’s a sweetheart but we’re not dating. We’re just friends. That’s about all there is right now.” Janet responded by saying they “swapped” more than good music.

8. Ryan Reynolds & Alanis Morrisette

It might come as a surprise, but Ryan Reynolds and Alanis Morrisette were once an item. In fact, this famous duo was once engaged but never made it to the altar. It’s possible that many people either didn’t know or simply forgot these two beautiful Canadians were a couple. Alanis Morrisette is a renowned musician best known for the albums Jagged Little Pill, Supposed Former Infatuation Junkie, and Under Rug Swept. Ryan Reynolds has starred in Van Wilder, The Amityville Horror, and Deadpool. Ryan and Alanis met in 2002 at Drew Barrymore’s birthday party. They became engaged in 2004 but the relationship didn’t work out and they broke up in 2007. Morrisette’s 2008 album, Flavors of Entanglement, was partly inspired by the pain she felt because of the split. She said, “I didn’t even realize it while I was writing the record, but it definitely goes through all the stages of grief.”

7. Conon O’Brien & Lisa Kudrow

Before she was the hilarious Phoebe Buffay and before he was the red-haired late night TV host, Conan and Lisa were a couple. One can only assume the relationship was filled with constant laughter. Lisa Kudrow is best known for her role on the sitcom Friends. Conan O’Brien previously hosted Late Night with Conan O’Brien and the Tonight Show with Conan O’Brien. He currently hosts the late night show, Conan. The unlikely pairing dated well before either was internationally known. They dated briefly after meeting at an improv class. At the time, Lisa was considering giving up acting but she credits Conan with encouraging her not to quit. Lisa once said about the relationship, “He was really smart, really funny, and he thought I was funny.” However, they quickly realized they didn’t have chemistry as a couple and that they make better friends. They’ve remained good friends after all these years.

6. Christian Bale & Drew Barrymore

Only Drew Barrymore can say she went on a date with Batman but never called him back. Drew Barrymore and Christian Bale both had their big breaks as children in Steven Spielberg films. Barrymore was 7 years old when she appeared in the blockbuster film E.T. and Bale was 13 years old when he starred in the critically-acclaimed film Empire of the Sun. When Barrymore and Bale were teenagers, they went on one date. In 2012, Bale discussed the sole date in Australian GQ and said, “We went to see some bloody awful horror film, and that was the end of it. She never called again.” He might have been disappointed at the time but he likely got over it. According to Barrymore, she had no problem with Bale but she was at a different place in her life and boys just weren’t a priority. She said, “I don’t know! He was so nice… I wasn’t like super boy crazy.”

5. Sofia Vergara & Enrique Iglesias

Some relationships fly under the radar because they dated well before either was a true superstar. That’s probably the reason most people don’t know that Sofia and Enrique once dated. In the ‘90s, Sofia Vergara was relatively unknown aside from her success in her native Columbia. Enrique Iglesias was the Latin sensation sweeping the nation. “The King of Latin Pop” has released several popular albums, including Cosas del Amor, Enrique, and Escape. Sofia Vergara is best known for her role as Gloria Delgado-Pritchett on the popular sitcom Modern Family. Before Sofia became one of the most popular actresses, she dated Enrique. This was all the way back in the ‘90s when every woman was chasing after him. However, for various reasons, the relationship just didn’t work out. Enrique is often linked to tennis star Anna Kournikova and Sofia married Joe Manganiello. Additionally, Sofia is now one of the most famous celebs in the world.

4. Justin Timberlake & Fergie

In his younger days, Justin Timberlake had a thing for older ladies. When he was 16 years old, he dated then 23-year-old Fergie. This was well before either one was the worldwide phenomenon they both came to be. Individually, they have toured the world and sold millions of albums. In 1996, when they first started dating, Fergie was still unknown and a member of the Wild Orchid. Justin was just a teenager but was on the verge of becoming a major star along with the rest of N’Sync. The relationship was pretty brief as it was not too long after Justin started his highly publicized relationship with Britney Spears. When discussing dating Justin, Fergie said, “Justin and I would go out together and have fun and make out,” She continued, “We were never serious. He was Mr. Right Now.” Justin went on to date a long list of gorgeous celebs but it all started with Fergie. He is now married to actress Jessica Biel.

3. Ryan Gosling & Sandra Bullock

Two of the most beautiful human beings ever born, Sandra Bullock and Ryan Gosling, once dated in a very low-key relationship. She is 16 years older than him but it didn’t seem to matter at all. Sandra has appeared in several universally praised films, such as Crash, The Blindside, and Gravity. Ryan has starred in his fair share of beloved movies, including The Notebook, Drive, and The Big Short. Sandra Bullock has been linked to several celebs, including Tate Donavan, Troy Aikman, and Matthew McConaughey. Gosling dated actress Rachel McAdams and is currently married to Eva Mendes. In 2001, Gosling was just about to become a breakout star and Bullock was still a beloved celeb. They dated for a year before breaking up in 2002, but neither regretted their time together. Gosling once said about both Bullock and McAdams, “I had two of the greatest girlfriends of all time. I haven’t met anybody who could top them.”

2. Amy Poehler & John Stamos

Amy Poehler once went on a date with John Stamos. Actually, she wasn’t 100 % certain it was a date. She said, “We were having dinner and I was like, ‘Oh, maybe this is a date!’ But I didn’t know.” Amy Poehler starred in Parks and Recreation and John Stamos is remembered for his role on Full House. They met while working on the 2014 film They Came Together. He asked her out for dinner but she said, “I remember thinking like, ‘Oh, s**t. Like, if this is really a date…’ I think I was wearing a Leslie Knope top. I think I was wearing a shirt from work. I wasn’t foxy.” During an interview, John Stamos cleared up the situation when he said, “I guess [Amy] didn’t know it was a date. I asked her out on a date…and we had a really nice time. Then I hear she thought it wasn’t a date. It was a date in my eyes.”

1. Madonna & Tupac

In 2014, iconic musician, Madonna, dropped a major bombshell when she revealed that she dated the legendary late rapper, Tupac Shakur. Madonna has released several chart-topping singles and sold out stadiums all over the world. Tupac is widely regarded as the greatest rapper of all time. They both found themselves in the headlines and the center of controversy. That’s likely part of the reason why they kept their relationship a tight-lip secret.

Madonna and Tupac first met at the 1993 Soul Train Music Awards. He had gone as actress Rosie Perez’s date after she was stood up. It was Perez that introduced Madonna and Tupac at the event, and they soon started dating. Madonna noted that he got her “riled up about life in general” and she felt “very gangsta.” She was in this frame of mind before her controversial appearance on Late Show with David Letterman in 1994. However, they broke up at some point in early 1995 before his prison sentence, which was roughly a year or so before his murder in September 1996. In the mid-90’s, the world famous “material girl” experienced what “thug life” was really all about.



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