The most unlikely celebrity couples

Unlikely celebrity couples have been making ours jaws drop ever since young Tom Cruise and Cher dated back in the ’80s (more on that later…) Well, we are now nearing the end of 2017, and nothing has changed. Many celebrities are still turning heads left and right with their unusual choice of partners. Of course, who are we to judge, right? Love is love, age is just a number, differences can be overcome with true compassion… and so on. Although love is apparently ‘blind’, we still can’t get over some of these celebs couples! What is going on? Does being famous make you attracted to people who are the exact opposite of you? Someone must get to the bottom of this.

Some of the celebrity relationships on this list are ‘unlikely’ due to age gaps. Now, we aren’t talking a few years older or younger, we are talking a good 40 and even 60 years age difference with some of these couples!


How is that even possible? How can someone be attracted to and relate to someone who is old enough to be their parent or even… grandparent. It tends to gross us out a bit, but again, who are we to judge really. Whatever floats your boat and all that.

Sometimes, it isn’t the age, but it is the height difference. Okay, perhaps it isn’t worth it to make a big fuss over a few inches, but a good two feet, well, that is a bit alarming and just raises a whole bunch of questions. However, we will say it once more. If they don’t care they, we shouldn’t either… or should we?

Lastly, there are relationships on this list that are odd, but we just can’t put our finger on the reason why. Yes, they are about the same age and height, sometimes they even have the same occupation, but it is just super random! (Like Seth MacFarlane and Amanda Bynes for example. And no, we aren’t joking.) They leave us asking questions like, “But why?” and “How did they even meet?” We are pretty sure that you will see some of your favorite celebs next to people you had no idea were ever even a thing.

We guarantee that the majority of relationships on this list will give you a bit of a shock, so it is best you are sitting down while reading this.

Courtney Stodden and Doug Hutchison

Another relationship that had us saying, “Why???” Actor Doug Hutchison crept back into the limelight in 2011, when the 52-year-old announced his marriage to 16-year-old Courtney Stodden, with permission by Courtney’s mom of course. They met virtually after she sent him an email about taking an acting workshop from him, and their relationship blossomed from there. Despite the loads of negative attention the couple received, they managed to stay together until a few months ago, when they announced their split.

Evan Rachel Wood and Marilyn Manson

Probably one of the most bizarre couples on this list… and in history, was Westworld’s Evan Rachel Wood and metal goth rock star Marilyn Manson. She started dating him in 2006, when she was only 19 and he was 36. The public went wild and called Evan a homewrecker, since the relationship began right after Marilyn’s split from his wife Dita Von Teese. Despite the negative criticism, the couple got engaged in 2010 only to break up shortly after.

Amber Tamblyn and David Cross

When Two and a Half Men actress Amber Tamblyn came out with Tobias from Arrested Development, the couple definitely had a few extra eyes looking their way. Yes, they are a cute and equally funny couple, but we do need to keep in mind that David Cross is 19 years older than Amber… that is like ‘old enough to be your dad’ older. Nonetheless the unlikely couple got married in 2012 and they are as happy as ever. Whatever floats your boat, right?

Chelsea Handler and 50 Cent

The quirky comedian and talk show host Chelsea Handler, dated rapper 50 Cent for a brief period of time. While they do look sweet together, it does seem like a pretty unusual couple! Chelsea opened up with Oprah Winfrey and described the rapper as a “sweetheart”. She said he came to her show in 2010 and even sent her flowers, guess the guy who raps about taking women to the ‘candy shop’ is a hopeless romantic after all!

Kat Dennings and Josh Groban

When Kat Dennings and Josh Groban first stepped onto the red carpet together back in 2014, many were a little confused and shocked at the odd couple. True, they are both beautiful, talented and famous people- but it still seems sort of strange. Kat is often seen as feisty and sarcastic and Josh, well he sings cheesy romantic and inspirational songs. Sadly, the unusual couple broke up mutually after a 2 year relationship.

Hugh Hefner and Crystal Harris

When the late Hugh Hefner married his playmate girlfriend Crystal Harris in 2012, they certainly turned a lot of heads. It might have been due to the fact that she was a whopping 60 years younger than him! On the other hand, we weren’t so shocked considering Hef’s history with younger women. The couple stayed happily married until he passed away earlier this year. Apparently, Crystal had signed a prenup before their wedding and she was not included in Hef’s Will.. so she must have actually loved him!

Katie Holmes and Tom Cruise

Katie Holmes and Tom Cruise, well… they actually made a lot of sense as a couple considering they are both beautiful and successful movie stars. The only thing that made us look twice was their height difference. Although Katie is only 2 inches taller than her ex, she would often wear heels on the red carpet which made it look like she was towering over a tiny Tom Cruise.

Tom Cruise and Cher

Slightly more unusual than his relationship with Katie was with Cher. The two dated for some time in 1987, when young Tom Cruise was just starting off in the business and Cher was at the peak of her career. Cher once described her ex-boyfriend who was 16 years younger than her as “shy”, but she did admit that she was “crazy for him.” But can we blame her? Who wouldn’t be crazy for young Tom Cruise!

Cameron Diaz and Benji Madden

Back in May 2014, the odd couple dated for a brief period of time. Although they are both equally good looking and talented in their own right, it was still a bit much for people to take in. America’s sweetheart with a tattooed Good Charlotte rock star? Even more surprising, their apparent mutual friend Nicole Richie set them up.. not random at all.

Mariah Carey and Nick Cannon

When diva Mariah Carey and former Nickelodeon star turned rapper Nick Cannon came out to the public in 2008, the media went wild. First of all, Mariah was known for dating older men, seeing as her previous husband Tommy Mottola was 20 years her senior. Second of all, it kind of just popped up out of nowhere. The two lovebirds, with 11 years between them, were married until their divorce in 2016 and have a set of adorable twins together.

Christina Hendricks and Geoffrey Arend

Christina Hendricks became quite the symbol after she appeared as the curvy and stunning red head Joan on Mad Men. She has been married to actor Geoffrey Arend since 2009, who let’s just say is a bit more average looking than his glamorous Marilyn Monroe-esque wife. Although Geoffrey had to fend off all of his wife’s new admirers, the couple are still happily married today.

Sophie Dahl and Jamie Cullum

Wow, talk about a height difference, but that is what you get when you marry a model! Sophie Dahl and singer Jamie Cullum don’t mind the six inch difference between them, and they tied the knot in 2010. Although Sophie did admit that she felt weird towering over her husband at first, the couple are now used to it and it doesn’t bother them whatsoever. They are still very much in love today and now are the parents to two children.

Johnny Depp and Amber Heard

Johnny Depp and Amber Heard…if you haven’t heard about their drama and recent divorce then you might as well be living under a rock. The couple, who have 22 years between them, met while co-staring as on-screen lovers in 2009’s The Rum Diary. They started dating later on, in 2012 and got married in 2015. After a messy breakup and divorce, the couple’s split was finally made official earlier this year in January.


James Woods and Ashley Madison/Kristen Baugness

James Woods is known for having a thing for younger women. We don’t mean 10 or 20 years younger, we are talking like 50 years younger. It all started in 2007 when he started dating 19-year-old Ashley Madison when he was 59-years-old. In 2013 James, who was 66 at the time, stepped out on the red carpet next to his newest 20-year-old ex-felon girlfriend Kristen Bauguess. We just have one question for these girls… why???

Colin Farrell and Elizabeth Taylor

Although their relationship was mostly kept in secrecy, actor Colin Farrell admitted to dating the famous Elizabeth Taylor for two years until her death in 2011. The relationship began after he sent her a bouquet of flowers when she returned home from the hospital after a surgery. Colin still thinks of Elizabeth, who was over 40 years his senior, as one of the greatest loves of his life.

Billy Corgan and Tila Tequila

Is there anything more random than reality TV star Tila Tequila dating Billy Corgan of The Smashing Pumpkins? Yeah, we didn’t think so. They made their red carpet debut as a couple in 2009 at Bravo’s A-List Awards. People were, to say the least, a bit confused. Not only is Tila under 5 feet and Billy is over 6 feet, the whole thing just seemed off. Anyways, their relationship didn’t last too long and was over before it ever truly began.

David Spade and Julie Bowen

David Spade is known for getting around in Hollywood… for some strange reason. He has dated some of the most beautiful blonde actresses in the business from Heather Locklear to Nicollete Sheirdan. He also dated Modern Family’s own Julie Bowen back in 2002. The unlikely couple hit it off for a year, and two years later Julie met her current husband, and father to her three children, Scott Phillips.

Hayden Panettiere and Wladimir Klitschko

Is that Hayden’s bodyguard or boyfriend? When 5ft 1″ actress Hayden Panettiere and 6ft 6″ Ukraainian boxer first walked out on the red carpet together, a few jaws dropped. They had an on-again-off-again relationship for a couple years up until 2011, when they reunited and got engaged in 2013. They are still happily together and are now the parents to a sweet two-year-old girl named Kaya.

Mollie King and David Gandy

Mollie King of the British girl group The Saturdays and Dolce & Gabbana model David Gandy make for one good-looking pair. The only thing that caught our attention? Mollie looks so tiny next to her man! While Mollie stands at a decent 5ft 4″, David is a whole 10 inches taller than her at 6ft 2″. Either way, they still looked beautiful together, but unfortunately it was not enough and they broke up in 2016 after a 5 year relationship.

Seth MacFarlane and Amanda Bynes

This list is getting stranger by the minute. Family Guy’s Seth Macfarlane dated former Nickelodeon sensation Amanda Bynes. Not only was their 12 year age gap a bit alarming, the whole thing was just.. well, super random. Who even knew that the two knew each other? Apparently Seth met her while she voiced a character on Family Guy. To be fair, they did date in 2008, before Amanda’s meltdown.

Avril Lavigne and Brody Jenner

She was a skater girl and he was a… reality TV star? Although the unusual pair turned some heads, they really didn’t care. In fact, they actually stayed together for a whole two years before deciding on ending the relationship. Avril even appeared on Keeping Up with the Kardashians for Brody’s stepsister’s two-part wedding extravaganza to Kris Humphries. Shortly after Kim said, “I do”, the couple called it quits.

Ashton Kutcher and Demi Moore

When That ’70s Show star and famed actress Demi Moore started dating in 2003, their relationship caused quite the stir. Ashton was only 25 at the time, and was known more for pranking celebs on Punk’d than he was for having serious relationships, and Demi was 41. Despite their 16 year age gap, the couple got married two years later and stayed together until a messy divorce in 2013.

Rosario Dawson and Danny Boyle

Rosario Dawson and Danny Boyle have got to be one of Hollywood’s more peculiar pairs. Rosario met Danny back in 2012 while starring as the lead role in Danny’s film, Trance. They were spotted cuddling behind scenes and watching the Olympics Opening Ceremony, which was directed by Danny himself. While it isn’t clear how long they were together, we have a feeling the 23 year age gap had something to do with it.

Renée Zellweger and Jack White

Do you remember when Bridget Jones star Renée Zellweger and White Stripes frontman dated? Well, we do. The surprising and random mix between good girl blonde and bad boy rocker delighted the celebrity tabloids. They stayed together for a year and a half and even were rumored to be engaged before they called it quits in 2004, and were both married to somebody else the following year! Talk about moving on quickly…

Sandra Bullock and Jesse James

Sandra is known for dating movie stars such as Tate Donovan, Matthew McConaughey and even Ryan Gosling. In 2005, she pulled a bit of a wild card when she married the famous motorcycle builder Jesse James. Although we couldn’t point it out, we knew he was trouble from the start and was never deserving of precious Sandra. He cheated on her shortly after Sandra won an Oscar for best Actress for her role in The Blind Side. And she was left raising their adopted son Louis alone.

Madonna and Michael Jackson

Actually, it kind of makes sense that the king and queen of pop would date at some point… or does it? We can’t make up our mind just yet, but the celebrity couple is certainly a bit shocking. Madonna recently revealed their secret relationship while she was a guest on James Corden’s Carpool Karaoke. She revealed that she was always the one who made the first move because he was “a little shy.”

Holland Taylor and Sarah Paulson

In December 2016, American Horror Story’s Sarah Paulson admitted to dating Holland Taylor aka Charlie and Alan’s superficial mother from Two and a Half Men. The 42-year-old describes her surprising relationship with the 74-year-old actress as the “most wonderful and extraordinary thing” that has happened to her life. Sarah is known for dating older women, and was with actress Cherry Jones, who is 18 years her senior, before Holland.

Lea Michele and Matthew Paetz

We all know and love Lea Michele from Glee, but when she first stepped out in public with model Matthew Paetz, we couldn’t help but take a second look. Yes, they are both good-looking, fit celebs, a likely match- but one thing seems off. It could be due to the fact that Matthew, who is 6ft 2″ makes Lea, who is 5ft 3″ look even shorter than she already is! The couple dated for two years until he broke her heart right before Valentine’s Day last year.

Kim Kardashian and Nick Lachey

Before either of Kim’s marriages and even before Nick met Jessica Simpson, these two were an actual item. The year was 2006, and Kim had yet to become the reality TV star that she is today. Nick, who was already a famous boyband singer, revealed years later that Kim used him to get famous. She apparently used to tip off paparazzi of their location so that she could get photographed with the 98 Degrees star. Nice one, Kim.

Ashley Olsen and Lance Armstrong

Back in 2007, a very unlikely relationship between Ashley Olsen and professional cyclist Lance Armstrong took place. The odd pair were caught one night kissing and cuddling at a bar in a New York City Hotel. Although it is still a bit unclear how these two random people even met, safe to say the couple didn’t mind the 15 year age gap between them. Their relationship ended after Ashley moved on to date The Hangover’s Justin Bartha.

Barbara Streisand and Andre Agassi

Professional tennis player Andre Agassi had a fling with the one and only Barbara Streisand during the early ’90s. It was actually a bit more than a fling, as the couple stayed together for a few years until they eventually went their separate ways. Barbara once called him “very intelligent” and “sensitive.” So why did they break up? We’re betting the nearly 30 years age difference between them could have had something to do with it.

Moby and Natalie Portman

Although the singer/DJ dealt with some rumors claiming that he was attracted to men, he proved everyone wrong when he stepped out with one of Hollywood’s most beautiful actresses, Natalie Portman, in 2001. Although the pair shocked many, it didn’t stop them from dating for a brief period of time until they decided to stay “just friends.” The singer had to deal with some intense “nerd wrath” and he once said, “You don’t date Luke Skywalker’s mom and not have them hate their guts.”

Soon-Yi Previn and Woody Allen

Probably one of the most controversial relationships in Hollywood… During the early ’90s, Woody Allen’s girlfriend at the time, actress Mia Farrow, found several inappropriate photos of her adopted daughter, Soon-Yi, on Woody’s phone. At the time Soon-Yi was 21 and Woody was 56. According to Woody, the relationship was okay considering he never acted like a “father figure” to Soon-Yi. Anyways, the couple went on to get married and now have two children.

Ryan Gosling and Sandra Bullock

This adorable and talented pair were actually in a serious relationship in 2002 for a year during Gosling’s pre-Notebook days. At the time, Sandra was already a well-established movie star and Ryan was still a new face in Hollywood. Of course, he ended up dating his Notebook costar Rachel McAdams shortly after so his relationship with Sandra, who is 16 years his senior, was soon forgotten by the media.

Britney Spears and Kevin Federline/Sam Asghari

The princess of pop has surprised us over the years with her unique relationships. When Britney married her backup dancer Kevin Federline in 2004, she certainly turned a few heads. They divorced after a brief 3 year marriage, and have two sons together. Britney is now making headlines once again for her relationship with 23-year-old Sam Asghari who is, surprise surprise, also a backup dancer who appeared in the singer’s Slumber Party music video. We are starting to see a pattern here..

Rhianna and Shia LaBeouf

Another super random and unlikely couple on this list, the gorgeous Rhianna, who is typically known for dating hot rappers like Drake, had a brief relationship with actor Shia LaBeouf back in 2007. And when we say brief we mean brief. According to Shia, their relationship “never got beyond one date”. In Rhianna’s defense, this was before Shia had his strange transformation.

Catherine Zeta Jones and Michael Douglas

This unlikely pair came out to the public as an official couple during 1999, and were married only one year later. Yes, they are both successful movie stars, but he is also old enough to be her father. Two kids and 18 years later, they are still considered one of the happiest couples in Hollywood, despite their 25 year age gap. Perhaps age is just a number after all?

Hafþór Júlíus Björnsson and Kelsey Henson

The Icelandic actor and strongman is probably best known for playing Ser Gregor aka The Mountain in the HBO series Game of Thrones. Photos of him and his Canadian girlfriend Kelsey Henson have recently gone viral, and it is easy to see why. As the actor stands at a staggering 6ft 9in tall and weighs 395 lbs, his girlfriend is just 5ft 2in. However, the couple doesn’t seem to mind their extreme height difference, and are frequently sharing photos of their cuteness on Instagram for everyone to see.

Mary-Kate and Oliver Sarkozy

Half of the Olsen duo said yes to millionaire French banker and brother of the former president of France Oliver Sarkozy in February 2014, and they got married the following year. Oliver seems a bit different than all the preppy guys she dated in her movies! Not only is her new husband 16 years older than her, he also towers over her by a good 12 inches (at least). However, they do seem happy so… why not?

James Goldstein and Anna Sergeevna

James Goldstein is a notorious playboy who goes to hundreds of NBA games every year, accompanied by stunning young models. How does he do it? We will never quite understand, but in 2014 he even went so far as to start dating one of them. Anna Sergeevna is a blonde bombshell, and was just 25 years old when she called herself the girlfriend of 71 year old Goldstein. That means he was literally old enough to be her grandfather. It doesn’t seem to have lasted, though.

Padma Lakshmi and Salman Rushdie

This unlikely pair met in 1999 at a party in New York, when Padma Lakshmi was 28 and Salman Rushdie was 51 and still married to his previous wife. Lakshmi, an Indian-American model who is also the host of Top Chef, and author Rushdie, tied the knot in 2004 and the marriage lasted three years. They seemed happy for a time, but then the marriage fell apart, and in 2016, Lakshmi released a scathing tell-all book about her relationships, including her marriage to Rushdie.

Shaquille O’Neal and Nicole Alexander/ Laticia Rolle

That’s right, we saved the best (and most unusual) couples for last. Former NBA star Shaquille O’Neal, who stands at a whopping 7 feet tall, dated the petite 5ft 1″ reality star Nicole Alexander in 2000, leaving us all a bit puzzled to say the least. Now in 2017, he is dating the slightly taller, 5ft 6″ Laticia Rolle, who despite her average height, he still manages to tower over.