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The 12 Most Unexpected Celebrity Hook-Ups

The 12 Most Unexpected Celebrity Hook-Ups

Did you know that these celebrities hooked up in the past? Well, now you do.

Whether it was an affair or a brief relationship, some of your favorite celebrities have had the most unexpected hook-ups in the past. Recently though, there have been other crazy hook-up rumors such as Kourtney Kardashian and Justin Beiber, or Kate Hudson and Nick Jonas.

Justin Beiber has always been friendly with the Kardashians, but he’s also been romantically linked to Kendall Jenner and now, the oldest of the sisters, Kourtney Kardashian. Things just don’t add up considering the Beibs is 15 years younger than the mom of three, who is 36 years old. It all started out with a night out in Los Angeles where the two were seen leaving a restaurant together and then hanging out at Universal Studios for Horror Nights. Not sure what was the deal there, but if the rumors are true, it will be considered as one of the most unexpected celebrity hook-ups down the road. As for Kate Hudson and Nick Jonas, another awkward rumored couple in terms of age difference, the two were first seen together canoodling during the weekend in Florida in late September. Recently, they were both spotted again at the same place in NYC. Again, who knows if the rumors between them are true but it will for sure be a surprise if they turn out to be.

So in honor of these two current, rumored couples, we take a look back at the past 12 Most Unexpected Celebrity Hook-Ups.

12. Justin Timberlake and Fergie


Two of the most recognized pop music artists dated briefly in the past. Justin Timberlake was 16 years old when he had a fling with Fergie, who was 23 at the time! The Black Eyed Peas member reveals to Australia’s Courier Mail that it was before he got serious with the pop queen, Britney Spears. To be honest, the two would have made such a good couple, once JT turned legal, of course. One of them is the man of pop music and has a reputation of just being down-to-earth. The other, is also a part of a big pop music move, being a member of the group, Black Eyed Peas, and she is also really liked in the industry. However, what was once just a fling, ended in 1996. According to the “Fergalicious” singer herself in a Cosmopolitan interview, the two would just go out and make out, having fun. “But we were never serious,” Fergie said. “He was Mr. Right Now.” Ouch. Hopefully, JT feels the same way about their romantic past.

11. Tom Cruise and Cher

Way before we had TomKat, and even before his first marriage, Tom Cruise once dated the iconic singer, Cher, back in the 80s. It seems though, that according to the songstress in an episode of Bravo’s Watch What Happens Live with Andy Cohen, she still doesn’t mind going back down memory lane of their romantic connection. The “Believe” singer named the Mission Impossible actor one of her top five lovers.

In another interview with Good Morning America, the 69-year-old pop sensation revealed that Cruise was not a scientologist when they were “seeing each other” but described him as “the most adorable man you can imagine.” She also once described him as a “shy boy” and “wonderful” and that she was “crazy about him.” From the looks of it, it seems like the Burlesque star enjoys gushing about her ex-boyfriend. If she could turn back the time, maybe the pop diva would have done things differently with the Golden Globe-winning actor.

10. Ryan Gosling and Sandra Bullock


What a cute couple, if we didn’t know who they actually were. When you think about it, it is kind of weird knowing that two of the most A-list actors in Hollywood, Ryan Gosling and Sandra Bullock, were an actual item. Yes, they dated in 2002 when they met on the set of their movie, Murder by Numbers, and fell in love. The Hollywood heartthrob gave the inside scoop on his past gfs, including Sandra Bullock, to UK-based newspaper The Times. He recalled, “I had two of the greatest girlfriends of all time. I haven’t met anybody who can top them.” This of course was said before he married Eva Mendes in 2011. The couple, though, did meet that same year as they were spotted in Disneyland on a private tour showing major PDA and holding hands. The Blue Valentine actor now is a father while Bullock is also a mother herself, but has stayed single for the most part after her disastrous divorce from Jesse James.

9. Ryan Reynolds and Scarlett Johansson


Although, it seems like this would be a well known couple that dated in the past, due to their high-profile lives, Ryan Reynold’s and Scarlett Johansson’s marriage was pretty low-key compared to all the hype surrounding his marriage to Blake Lively. The Lucy actress and The Proposal actor married in September 2008 in an intimate ceremony but later split in 2011. The Vanity Fair cover girl opens up to the magazine about the relationship with the actor saying she learned about what she needs and what she wants in a relationship. “And I know I have more tools to communicate, not just with my partner, but with myself.”

She later clarifies to the publication, “that’s not necessarily any reflection of who I was married to or what was happening in my marriage, but really where I was in my life.” The bombshell actress is now settled down with French journalist Romain Dauriac, who she finds refreshing considering he’s not in the acting industry. Reynolds is now married to his Green Lantern co-star, Blake Lively.

8. Janet Jackson and Matthew McConaughey


It is getting hot in here and even weirder. Indeed, several reports suggested Janet Jackson and Matthew McConaughey were linked romantically to each other in a brief fling and it all started during the night of the 2002 Grammy Awards. Their hook-up does make sense, considering how hot they both are as individuals. However, for some reason, the two just make an odd couple overall.

According to, the two hit it off that night and then headed to her Bel Air home where they had a steamy night session. The two though never confirmed those rumors of them hooking up, but they both said good things about each other. McConaughey called Jackson a “dear lady.” Fast-forward a few years, the Magic Mike actor married model Camila Alves, who became one of our favorite Hollywood couples. They have three kids together. As for Miss Jackson, the “Rhythm Nation” singer married executive director, Wissam Al Mana.

7. Kim Kardashian and Kris Humphries


The fact that their marriage lasted only 72 days says everything about how odd this relationship was because it just wasn’t meant to be. If you watched Kim and Kourtney Take New York, then you saw how head over heels Kim Kardashian was for NBA player, Kris Humphries. Normally, the reality TV personality goes for a darker shade when it comes to boyfriends, so we don’t really know what exactly attracted her to the basketball athlete. Regardless, the two “hit it off” and Kardashian said so herself that she was a hopeless romantic and couldn’t help but fall for the 30-year-old. That all lead to an extravaganza of a wedding that cost an estimated $10 million.

The socialite reportedly received a $2-million, 20.5 carat engagement ring. However, as we all know, the couple soon divorced after only 72 days of marriage, calling it off due to “irreconcilable differences.” Again, if you did watch the Kardashian spin-off series on the E! Network, you could tell the two had opposite personalities which didn’t make them compatible as a couple. It all made sense for them to go their separate ways.

6. Ryan Reynolds and Melissa Joan Hart


Oh yes it is him again, but this time, it wasn’t a marriage. In an exclusive interview with Giuliana Rancic on E!, Melissa Joan Hart confessed on some things we didn’t know about the star of Sabrina, The Teenage Witch, including her love life. Although she was in a relationship then, the actress shared that she once locked lips with Ryan Reynolds behind the scenes of the Sabrina, The Teenage Witch TV movie. On their last day of shooting, the Green Lantern actor supposedly gave her a Bulova watch and that is all it took for Hart to react and do what her heart desired. She then “chased” the actor to his car and the two ended up making out all night. “Then I had to call my boyfriend the next day and explain it,” she told Rancic.

Apparently, the TV actress was the one to start the fling and end the fling as well before it got serious. After all, she did have a boyfriend. “I think he wanted something more,” she said. “But I decided I was going to stick with my boyfriend.”

5. Enrique Iglesias and Sofia Vergara


Remember when we said it’s getting hot in here? Well, it just got hotter. According to several reports, Sofia Vergara briefly dated Enrique Iglesias before she settled down with her now husband, Joe Manganiello. While the two Latin superstars were dating and hitting it off, the “Bailando” singer was more famous than the Modern Family actress. She wasn’t that well known in Hollywood. Well that has changed. Not much was heard about the two and their relationship then, but it looks like it wasn’t meant to be as both have definitely found their soul mates.

Vergara and Manganiello began dating in 2014 after the Colombian actress broke up with ex-fiancé, Nick Leob. The two obviously created some steam when rumors started going around about them hooking up. Everyone was so happy that those rumors ended up true. While that couple is still fresh, Iglesias and Anna Kournikova have been love birds since 2001! That is a record for a Hollywood couple.

4. Tyra Banks and Will Smith


While on their way to stardom, Tyra Banks and Will Smith dated from 1993-1994. If the two stayed together, they probably would have been the Jay-Z and Beyoncé of today. The two have gone on to become business moguls in their own right. We can’t imagine what a power couple they would have been if their brief relationship lasted. The America’s Next Top Model star made a few appearances on Fresh Prince of Bel Air where their characters were also romantically linked. At least we got a taste of what a Will Smith and Tyra Banks relationship would be like.

Even though they would have been Hollywood’s “it” couple, they both have ended up in good relationships. Will Smith has Jada Pinkett Smith. The couple have been married since 1997 and have two kids, Jaden Smith and Willow Smith. Banks has also been seen out with her new man, Eric Asla, in West Hollywood flirting and certainly displaying a notion of happiness between the two.

3. Ashley Olsen and Lance Armstrong


Back in 2007, Lance Armstrong and Ashley Olsen reportedly dated, but the fling didn’t last for too long. According to a tell-all book about the cyclist by Juliet Macur, called Cycle of Lies: The Fall of Lance Armstrong, there was some trouble surrounding their romance and Armstrong’s friends. One friend who goes by the name of John Korioth, didn’t think the pair was a good idea for the athlete’s image in terms of their age; Olsen was 15 years his junior. Not only was it their age difference that caused issues for the couple, but Armstrong just broke up with designer, Tony Burch, weeks before he got with the child star. Although, they had a few issues to deal with, they managed to maintain their relationship or fling or whatever it was for almost a year, from May to December. In contrast to all the hating this couple went through, Bob Saget weighed in and the pair got the former Full House actor’s approval. According to the Huffington Post, Saget told the publication, “I like Lance, Lance Armstrong is an amazing guy! Amazing guy!”

2. Natalie Portman and Moby

Apparently, Moby and Natalie Portman had a thing back in 2001. Despite of all the “gay” rumors and backlash the singer-songwriter had, the two very well did date back in the day. He even revealed more info than he would have wanted to in an interview with Spin regarding his relationship with the “Black Swan” actress. “I guess in some people’s eyes, I might be mildly sexy and as a nerd I’m certainly happy to enjoy some of the effects of that,” Moby tells the publication. “But as far as the very brief affair I had with Natalie, it’s made me the target of a lot of nerd wrath. You can’t date Luke Skywalker’s mom and not have them hate your guts.”

The DJ was still a target for a few homo-sexual bashes as everyone was waiting for him to finally come out, especially when his relationship with the stunning actress ended. Regardless, the two have moved forward since. Natalie Portman is now married to Benjamin Millepied while Moby’s last girlfriend that we know about was Kelly Tisdale.

1. Madonna and Tupac


Two of the most legendary musicians had collaborated in the past, and not in a music way, but in a romantic way. In an interview with Howard Stern on his SiriusXM radio show, Madonna revealed she had dated rapper, Tupac Shakur, just three years before he was murdered in 1996. According to the “Material Girl” singer, the two were introduced by actress, Rosie Perez, at the 1993 Soul Train Music Awards in Los Angeles. From there, the pair hit it off and began to date seriously. Madonna had told Stern that during her interview with David Letterman on The Late Show, the “California Love” rapper got her “all riled up about life in general” which is why she was noticeably cussing a lot during the show.

Perez also opened about the musicians’ relationship during The Wendy Williams Show and confirmed the rumors surrounding the pair. The actress also confessed on The View that it was Madonna who came up to her to ask to be introduced to the “Thug Life” rapper and so, Perez did and admitted she was happy that she did it. Lucy O’Brien got involved with the relationship, too, in her 2007 unauthorized book, Like An Icon, discussing that the “Vogue” singer was serious about her relationship with the hit-making rapper that she eventually wanted to start a family with him. To this day though, Madonna remains hush-hush about her relationship with Shakur, who was shot and killed in 1996. The pair did make an eye-catching couple so we could imagine all the attention they would be getting if they were still dating. They would probably be a better version of “Kimye” today.


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