Who doesn’t love keeping up with celebrity couples? It seems to always be two attractive talented people who come together and create this power couple. Not to mention, they tend to have beautiful babies as well. While love comes in all different shapes and sizes, some couples can still make us do a double-take when we see them together for the first time. Whether they seem to be somewhat mismatched, have a significant age gap, or look like they come from two different worlds, some couples baffle us.
Naya Rivera and David Spade
Back in 2017, the 31-year-old Glee actress was spotted spending some quality time with actor David Spade, who’s 53 years old. When pictures of the twp in a pool together surfaced, people online were freaking out about the unlikely couple.
People were actually convinced that it had to be an April Fool’s joke. Well, the couple reportedly dated for a few months before breaking it off. It turns out that Naya and David go way back. All the way back to the days when she guest-starred on his sitcom, 8 Simple Rules, in 2004.
David Cross and Amber Tamblyn
We might just be confusing David with his Arrested Development character, Tobias, but the 53-year-old actor seems to be a rather odd match for 34-year-old actress Amber Tamblyn. Recently, Cross was accused of making bigoted comments towards actress Charlyne Yi. He offered a controversial apology, saying that he didn’t remember the situation in the way that the actress described.
However, this couple got married in 2012 and welcomed a daughter named Marlow. Initially, the couple introduced their baby as Dauphinoise Petunia Brittany Scheherazade Von Funkinstein Mustard Witch RBG Cross Tamblyn-Bey jr. – as a joke. Ha.
Mary-Kate Olsen and Olivier Sarkozy
When Mary-Kate Olsen began dating French banker Olivier Sarkozy, eyebrows were raised all over the world thanks to their 17-year age difference. While that isn’t totally unheard of – especially in Hollywood – this couple is most definitely not a conventional celebrity couple.
These two got married in a private ceremony in New York back in 2015 when Mary-Kate was 29-years-old and Olivier was 46-years-old. They had been dating for three years by that point. It turns out that Olivier was ready to get married much sooner, but Mary-Kate wanted to wait.
Ashley Olsen and Richard Sachs
Ashley, the second half of the Olsen twins, also began dating a much older man. She dated 65-year-old financier and art-dealer, Richard Sachs. The 31-year-old dated Sachs for several months, during which the two were pictured getting cozy a few times.
Eventually, Ashley decided to end things. It’s been said she did so because she wanted to focus on her work as a fashion designer, especially the brand Elizabeth and James. She co-owns this company with her sister, Mary-Kate.
David Hasselhoff and Hayley Roberts
This one we can almost understand – he is The Hoff, after all. Not to mention, he looks pretty good at age 65. The actor and his 37-year-old Welsh girlfriend have been dating since 2013. In fact, the two are now engaged.
Hayley used to work at a shop in Wales, making just £6 an hour. One night, she was hanging out with her sister in a Cardiff hotel bar when David went inside. She went over and asked him for a photo. Then, the actor asked her for her number, and the rest is history!
Steven Tyler and Aimee Preston
The incredible 69-year-old Aerosmith singer is currently dating his 29-year-old assistant, Aimee Preston. The two are rumored to be engaged when Aimee was spotted wearing a diamond ring on her ring finger. However, no official announcement has been made by the couple
With their 40 year difference, some would argue that this relationship is ridiculous, especially since Aimee is older than just one of Steven’s daughters. As you’d expect, this can make things somewhat awkward for the family.
Kristen Bell and Dax Shepard
Kristen Bell and Dax Shepard seem to be almost the exact opposites. While the actress was raised as a Christian good girl, Dax had a rather difficult life story. He’d been dealing with substance abuse for years. Well, the two didn’t hit it off immediately.
Eventually, however, they ended up falling in love. Now, they’re one of the cutest couples in Hollywood, sharing videos of their home life and wearing matching sweaters. Still, the couple has spoken about how their relationship takes a lot of hard work.
Seth Green and Clare Grant
We adore the hilarious Seth Green, but it’s clear that his wife outshines him when they walk the red carpet together. Seth met the actress at a reopening of the two’s favorite comic-book store. There, he was handing out autographs and she was a photographer for the event.
When they first started dating, they were both amazed by just how much they had in common. In fact, the adorable couple has since teamed up for Seth’s stop motion sketch show, Robot Chicken.
Cynthia Nixon and Christine Marinoni
Cynthia Nixon, the SATC actress, also ran for governor of New York back in 2018 and has been dating LGBT activist Christine Marinoni since 2004. Cynthia has spoken about how Christine’s appearance was what drew her to the activist in the first place.
It turns out that the actress had never dated a woman before that. She explained, “It wasn’t something in me that was waiting to come out. It was like, ‘This person is undeniable. How can I let this person walk by?’”
Seth Rogen and Lauren Miller
Seth Rogen definitely has that ‘geeky’ look going on, but that didn’t stop him from ending up with the beautiful actress, Lauren Miller. The couple met back in 2005 at a birthday party. After that, they had a very romantic-comedy like first date.
The two went for grilled-cheese sandwiches at four in the morning and stayed up until sunrise playing Spanish Scrabble. On their next date, they went mini-golfing and got into a hit-and-run accident. In fact, that had brought the two closer together – the cute couple has been married since 2011.
Hugh Jackman and Deborra-Lee Furness
While it’s rather common for women to date older men in Hollywood, men who date older women is a rather refreshing change. Hugh could most likely get just about any woman he could ever want, but his heart lies with his wife of 21 years, Deborra-Lee Furness.
The couple met when Hugh was in his early ’20s and had his first acting job on an Australian TV show. The show starred his now-wife, who is 13-year-older than the actor. Hugh said that the two became a team and were “madly in love”.
Evan Rachel Wood and Marilyn Manson
While we knew Evan Rachel Wood had a dark side, when she started dating musician Marilyn Manson in 2007, her fans were absolutely shocked. At the time, the Westworld actress was only 18 years old and Manson was 18 years older than her and still married to Dita Von Teese.
The two dated on-and-off and even got engaged in 2010 but broke it off later the same year. Their relationship was strange, to say the least. Manson’s song “I Want to Kill You Like They Do in The Movies” was said to be written about Wood.
Malin Akerman and Roberto Zincone
Malin Akerman is a truly breathtaking woman and a talented actress, so it only makes sense that any man would feel like the luckiest man alive to marry her, especially Roberto Zincone. Apparently, Roberto was the one who filed for divorce.
After being married for six years, and just a few months after having a baby together, the Petalstones drummer called it quits in 2013. Malin has since moved on. She’s gotten engaged in 2017 to actor Jack Donnelly.
Salma Hayek and François-Henri Pinault
We can all agree that Salma Hayek looks absolutely unbelievable for her age. While her husband isn’t all that much older than her, he’s most definitely lucky to have ended up with the actress. Apparently, Selma’s friends thought it was the other way around.
François-Henri happens to be the CEO of Kering – the brand that owns fashion brands like Gucci, Louis Vuitton, and Alexander McQueen. Since Selma never really cared about fashion, she remembers her fashionista friends saying to her, “How did you of all people land this guy?”
Julia Roberts and Lyle Lovett
Remember when gorgeous actress Julia Roberts married the funny-haired country singer, Lyle Lovett? This couple seemed so odd and out of place, they were named “beauty and the beast” by the press. Ouch.
The two met on the set of 1992 movie, The Plater. It’s been said that they dated for three weeks before getting married. After their quiet wedding, Roberts went up on stage in her wedding dress at Lovett’s concert and announced the two were married. However, in 1995, the couple split.
Anne Hathaway and Adam Shulman
Anne Hathaway started dating the actor and jewelry designer Adam Shulman back in 2008. The two got married in 2012. Yes, we’ll say it: Anne is stunning and Adam is rocking a somewhat geeky look.
After her former partner, Raffaello Follieri turned out to be a con-man and went to jail for things like fraud and money-laundering, we think he’s a major step-up. The actress has said her relationship with Adam is more mellow than her past romances, saying, “It makes for a good life.”
Howard Stern and Beth Ostrosky Stern
The radio and TV personality Howard Stern is famous for pushing the boundaries and creating controversies. The 64-year-old has been married since 2008 to the former model and actress, Beth Ostrosky Stern, who’s 19 years younger than him.
According to Beth, she feels very lucky and that “everything Howard does is romantic. The two have even fostered hundreds of cats for adoption in order to save them from being put down! How sweet is that?
Matt Bomer and Simon Halls
Seeing as he’s a beautiful man, it’s understandable why so many women were disappointed to find out Matt Bomer was actually into men. He revealed his marriage to Hollywood publicist Simon Halls back in 2012 while accepting an award. He thanked his beautiful family, Simon, and their three children.
Simon is most definitely handsome, but with their 14-age difference, some would say that he isn’t who they imagined Matt Bomer would end up marrying. However, the couple is definitely swoon-worthy in our opinion.
Rupert Murdoch and Jerry Hall
Former supermodel and actress Jerry Hall used to be in a serious relationship with Mick Jagger, but the two never legally got married. Nowadays, she’s married to media mogul, Rupert Murdoch, who’s 86-years-old.
There’s no doubt that Rupert is a lucky man to be married to the stunning former model, but he is one of the most influential people in the world since he’s the head and founder of News Corporation. These two make quite the power couple.
Jesse Williams and Aryn Drake-Lee
Jesse Williams and Aryn Drake-Lee got married back in 2012. However, being an actor who’s married to somebody outside the industry is no easy feat – his wide was a real-estate broker herself. Well, the couple separated in 2017.
The actor denied the rumors claiming he ended the marriage for another woman. He called it “the most painful experience I’ve had in my life.” Not to mention, the couple got into a custody battle over their two kids, ending up agreeing on joint custody.
Cameron Diaz and Benji Madden
Cameron Diaz and Good Charlotte guitarist, Benji Madden got married in 2015. Cameron knew her husband’s twin brother, Joel Madden, as well as his wife, Nicole Richie. However, Cameron didn’t officially meet Benji until she hosted a dinner party and asked Joel to invite him as well.
While Benji doesn’t fit the general type of man that Cameron has previously dated, Cameron said, “I’d never been loved in that way. I look at him every day and he inspires me.” How sweet is that?
Sarah Jessica Parker and Matthew Broderick
Sarah Jessica Parker has become famous for her role as the fashion icon, Carrie, in the hit show, Sex and the City. However, her relationship with her husband and fellow actor, Matthew Broderick is nothing like Carrie’s and Mr. Big.
The cute couple first met while working in theater and got married back in 1997. They had a surprise wedding ceremony – their guests were sure they were attending a party! Currently, the two live in New York and are raising their three kids together.
Katy Perry and Russell Brand
A lot of people were surprised to find out that the pop singer Katy Perry started dating comedian and actor, Russell Brand. He’s mainly known for being outrageous. In fact, the couple got married in 2010, but their marriage ended just 14 months later.
It turns out that the comedian told Katy he wanted a divorce – through a text message. Ouch. On top of that, Russell spoke about Katy in his documentary as a “mindless celebrity”. Later, however, he regretted his choice of words, saying their marriage didn’t last “due to the undulating nature of fame.”
Billy Bob Thornton and Angelina Jolie
It’s no secret that Angelina Jolie, the actress and humanitarian, was once married to fellow actor Billy Bob Thornton, or that they got each other’s names tattooed on their bodies. That sounds rather permanent, wouldn’t you say?
Apparently, it wouldn’t be. Being married to one of the most beautiful women in the world isn’t easy. “I never felt good enough for her,” Billy said. “If you believe somebody’s too good for you, you’re going to mess it up.”
Julie Bowen and Scott Phillips
The Modern Family actress, Julie Bowen married her husband, real estate investor, Scott Phillips in 2004. While Julie might have a stable relationship with her funny on-screen husband, Phil, her real-life relationship was not like that.
Just like many other celebrities who married people outside of the industry, their marriage ended. Unfortunately, the actress filed for divorce in early February 2018, after more than 13 years of marriage. She requested joint custody over the couple’s three boys.
Al Pacino and Lucila Solá
The famous Godfather, Al Pacino himself, has been dating fellow actress Lucila Sola since 2012. The power couple has a significant age gap between them – 39 years, to be exact. Al is currently 79 and Lucila is only 40-years-old.
Thinking about that, this means that if it were a person, their age difference would be just one year older than Lucila. However, when Al was asked about the possibility of them getting married, the actor replied, “I never say never. It’s possible.”
Danny Boyle and Rosario Dawson
38-year-old actress Rosario Dawson dated the famous director, Danny Boyle (aged 61) when they worked together on the film Trance. The couple seemed to be involved in a short-lived, intense, whirlwind romance. However, they kept their relationship very quiet.
When she was asked about their breakup, Rosario responded, “I love Danny. He’s wonderful and we dated longer than people think we did.” She continued, “From the outside it looks like there’s a lot of dissimilarities, but we actually have a lot in common.”
Christie Brinkley and Billy Joel
Supermodel Christie Brinkley still looks just as incredible today, as she did in her youth. However, there’s no doubt that back in the day, she was absolutely breathtaking. The model met Billy Joel in the ’80s. When Christine starred in Billy’s music video – Uptown Girl, the two got closer.
Eventually, the couple got married in 1985. Their marriage ended up lasting 10 whole years! While Billy was already a famous and successful singer by that time, his looks were no match for the model’s stunning beauty.
Kate Gorney and TJ Miller
While it looks like they were contestants on Beauty and the Geek, the Silicon Valley star, T.J. Miller met his wife, actress Kate Gorney, over a decade ago, when they were in college together. The couple tied the knot in 2015.
T.J. proposed to Kate in the Lost Angeles County Museum of Art – “because she is a work of art,” according to him. Apparently, though, the proposal was somewhat painful. “I went down fast, and it really hurt my knee,” T.J. said. “But I got through it, and she said yes.”
Marisa Miller and Griffin Guess
If you’ve ever wondered what kind of guy would be lucky enough to marry a Victoria’s Secret supermodel like Marisa Miller, we’ve got the answer. It turns out that it’s someone like Griffin Guess. He’s an entrepreneur and music producer.
In fact, he’s worked with the likes of Eminem, Jay Z, and Kanye West. While he’s an impressive man, he’d not as impressive looking as his supermodel wife. The couple got married back in 2006 and are now raising two children together.
Alexis Bledel and Vincent Kartheiser
The stunning Gilmore Girls actress met Vincent Kartheiser while playing a recurring character on the famous show, Mad Men. Vincent was a regular on the show. The couple got married in 2014 and had their first child a year later.
Jon Hamm commented on their romance, saying, “I did know he liked her from a very early point. I was a supporter of that union.” While Alexis might be considered to be more attractive than her husband, if Don Draper himself approves, so do we.
Christina Aguilera and Jordan Bratman
Christina Aguilera started her career in the Mickey Mouse Club and later became a teen pop sensation. Not to mention, she’s now one of the most famous artists in the world. The Grammy winner met her former husband, music producer Jordan Bratman when she was 21 years old.
The two got married three years later and even had a child together. However, Christina, later on, realized she was unhappy and needed to move on. Still, she only has good things to say about Jordan.
Felicity Huffman and William H. Macy
Some might say that the Desperate Housewives actress, Felicity Huffman is more attractive than William H. Macy, but you can’t argue with a 20-year-long marriage! The couple met back in the early 1980s and it was love at first sight.
However, Felicity didn’t really believe in marriage and turned down William several times when he proposed. After the couple broke up for almost five years, she decided to finally accept his proposal. Since then, the two have only gotten stronger.
Macaulay Culkin and Mila Kunis
There aren’t too many people who remember this, but That ’70s Show star, Mila Kunis once dated the Home Alone actor, Macaulay Culkin. The two dated between 2002 and 2011. Throughout their relationship, they did their best to keep it private.
While Mila is typically seen as more attractive, it’s Macaulay that attracted fan’s attention in the street. “He was huge. You couldn’t walk down the street with him,” Mila said. “Fans just screamed when they saw him!” Nowadays, she’s married to Ashton Kutcher, of course.
Tina Fey and Jeff Richmond
Tina Fey is known for her amazing humor, great mind, and her beauty – overall, she’s just good at everything. She met her husband, composer Jeff Richmond a long time before she became famous. The two fell in love after spending an afternoon at Chicago’s Museum of Science and Industry.
In fact, Jeff actually said their marriage is “borderline boring—in a good way,” and Tina agrees. “I don’t have that kind of ‘I love the bad guys’ thing. No, no thank you. I like nice people.” It sounds like these two will be good together for a long time!
Emilia Clarke and Seth MacFarlane
Back in 2012, Game of Thrones actress, Emilia Clarke was seen with the Family Guy creator, Seth MacFarlane together getting cozy. Naturally, we love this hilarious guy. But, seeing how Emilia is considered to be one of the prettiest women in the world, many people said he was lucky to be dating her.
Emilia even spoke out about how, at times, strangers would express their opinions about the relationship. She said she didn’t react well to it at all. Unfortunately, the couple ended things the next year.
Mickey Rourke and Anastassija Makarenko
The 65-year-old actor and former boxer has developed a history of unstable relationships. And so, when he started dating 32-year-old Russian model, Anastassija Makarenko, no one thought it would last all that long.
Even the actor himself didn’t think the relationship would be serious. However, this couple has been dating since 2009! Mickey gushed about the model, “She’s a gift from heaven. Obviously she’s a very beautiful woman,” while she said, “He’s the most beautiful man in the world, he’s a sweetheart and the best boyfriend.”
Padma Lakshmi and Salman Rushdie
The stunning Top Chef host, Padma Lakshmi was once married to the renowned novelist Salman Rushdie. He’s 23 years older than her. The couple was married for four years, from 2004 to 2007, before things went sour.
In her biography, Padma wrote all about the failed marriage. She said Salman used to bring her breakfast in bed each morning at first, but as time went on, he became very cold and unsupportive.
Tom Cruise and Cher
This might be hard to believe, but Tom Cruise and Cher had dated back in the 1980s. While the two are both iconic in their own ways, this picture of them alone should be more than enough to explain why it was unlikely they would date.
Just their fashion sense differences were enough to show that. Not to mention, Cher was 16 years older than Tom at the time. In a way, though, they do seem to somehow complement each other well. To this day, Cher speaks highly of the actor.
Chris Pratt and Katherine Schwarzenegger
Chris Pratt has become one of Hollywood’s most diverse actors thanks to all the different roles he’s played so far. Some people recall him as Andy Dwyer from Parks and Rec, while others recognize him solely from Guardians of the Galaxy.
Either way, most fans would have never guessed that he would end up with Katherine Schwarzenegger. However, it seems to really be working – the two are now married and expecting their first child together.
Kat Dennings and Josh Groban
Even though Kat Dennings and Josh Groban aren’t together anymore, they were dating for almost two years. Clearly, the two had very serious feelings towards one another at the time. Lots of people were surprised when they first announced their relationship.
Since these two were never really seen together, their relationship took fans by surprise. Still, their relationship began in a really cute way. Kat tole ellen she liked Josh because of his Twitter account!
Kate Beckinsale and Pete Davidson
Most of us think of Pete Davidson as dating his former fiance, Ariana Grande. Well, their relationship wasn’t all that unexpected. However, his relationship with Kate Beckinsale definitely was. But, if you look closely, it’s not as odd as you might think.
The two are both in show business and most likely have ties thanks to that. Still, the age difference was slightly significant – Pete was 25 at the time while Kate was 45. It turns out that she likes younger men – she was quoted saying so herself.
Fergie and Justin Timberlake
It’s been some time since this was a thing, but once upon a time, Fergie and Justin Timberlake were happily dating. While it might not sound all that strange now, back then, it was completely unexpected.
The main reason was since Justing was only 16 at the time while Fergie was 23. How did anyone let this happen? Either way, their age gap clearly didn’t stop him. Still, the relationship didn’t last long before Justin set eyes on Britney.
Julie Bowen and David Spade
The loveable Clair Dunphy from Modern Family, Julie Bowen, once dated none other than David Spade. We don’t blame you if you can’t picture the actress with anyone other than Phil – we have the same problem.
Still, these two did date for about a year back in 2002. This was a time when celebrities we’d never expect to see each other were matched up. Bowen now has three kids with another man but is divorced.
Lady Gaga and Taylor Kinney
We all know how Lady Gaga loves being over the top – that’s one of the reasons we love her! While she’s toned it down slightly over the past few years, back in 2014 her image was as wild as it ever was. She didn’t hold back in the slightest.
This is what made it so interesting that she began dating Taylor Kinney. We’re not saying he isn’t good looking – not at all. However, he is a bit more “ordinary” compared to Mother Monster herself.
Jesse James and Sandra Bullock
For a while, Sandra Bullock had a rather consistent dating history. Her type seemed to be fellow actors who were huge movie stars, like Mattew McConaughey and Ryan Gosling. That’s why it was so surprising when she married Jessie James.
It seemed like the two married at random in 205. For those who don’t know, James is a motorcycle builder – not an actor. The two were married for about five years before getting divorced as a result of James’ infidelity.
LeAnn Rimes and Tiger Woods
If you’re a fan of country music, you’ll know who LeAnn Rimes is. Lots of people, however, might have forgotten that she used to date pro golfer, Tiger Woods, for a little while. There is a slight difference between the two’s professions, but their ages were slightly different, too.
Tiger was 7 years older than Rimes. Since their split, Tiger had been married Elin Nordegren and gotten divorced. We’re sure you remember all the drama surrounding that scandal, so we won’t get into it. Those days were definitely simpler times.
Chelsea Handler and 50 Cent
There’s something so sweet about the short-lives relationship between Chelsea Handler and 50 Center. For those who’ve forgotten, go look up 50 Cent’s appearance on Chelsea Handler’s show. That was the first time they had ever met.
Their chemistry was clearly there from that first moment. The two dated for a few months, but it turns out that it wasn’t so serious. We still kinda wish they’d get back together at some point – they play off each other so well!
Dennis Quaid and Laura Savoie
Movie star Dennis Quaid has had some highly publicized relationships over the years. His relationship with Meg Ryan might have just been the most famous one. Nowadays, however, Dennis has a new lady – Ph.D. student Laura Savoie.
Wait… Student? Yep, you read that right. These two are 39 years apart in age. That’s a big one. All the same, they seem to really be in love. Dennis has said that Laura is the one and they plan on getting married once the pandemic calms down.
Channing Tatum and Jessie J
A short time after he divorced his long-term wife, actor Channing Tatum began dating Jessie J, the English singer. The two have had some ups and downs, but they’ve been together for a while now. Now that we look at them, we guess we shouldn’t have been too surprised.
The two have movie-star good looks and are crazy talented. It would have been more surprising if Channing started dating a random person no one knew about. Still, that would have validated lots of daydreams in the world.
Hugh Hefner and Crystal Harris
When you see this photo for the first time, it might be slightly shocking. It’s pretty obvious why. However, once you see the names above it, it all starts making sense all of a sudden. We aren’t gonna speak badly of the late Hef.
Although, let’s just say that friendships with younger women weren’t out of the norm for him. In fact, Crystal was Hugh’s third wife – the two were married up until his passing. In total, they were married for 5 years. Crystal was only 25-years-old.
Olivia Wilde and Jason Sudeikis
An interesting couple that has definitely stood the test of time is Olivia Wilde and Jason Sudeikis. Olivia was said to be pretty nervous to approach him. She even went as far as saying he was out of her league.
It turns out that wasn’t the case. This couple has been together since 2011 and they are still going strong! They now have two children together, one born in 2014 and the second in 2016. While they aren’t married yet, they are engaged.
Chad Kroeger and Avril Lavigne
While he’s not a skater boy, Avril still was into him! Once upon a time, the queen of pop-punk was with the frontman of Nickleback. The two got married in 2013 and ended up separating in 2015. On top of being married, the two worked together in music as well.
You might be thinking that their marriage was relatively short, but their relationship lasted even less time. They only dated for a month before Chad proposed! We guess there’s not much to say other than what goes up must come down.
Lady Gaga and Michael Polansky
The little monsters will always be obsessing over who Lady Gaga is currently dating. That’s just the way this fanbase works, and there’s nothing wrong with that! Gaga definitely has an interesting history with men.
Michael Polansky is a businessman with absolutely no ties to the entertainment industry. Maybe Gaga wanted a guy to keep her grounded. Honestly, your guess is as good as ours. Of course, her mind is a wonderful enigma.
Emmy Rossum and Justin Siegel
You might recognize Emmy Rossum from the television show, Shameless. One completely unexpected thing was her marriage to music producer, Justin Siegel. In fact, it came as a total surprise to the actress’s fans.
They were surprised most likely due to the fact that the couple kept it a secret. It’s a celebrity marriage no one knew about! However, this couple ended up getting divorced a year and a half later, for the record.
Katheryn Bigalow and James Cameron
Don’t let James’ hair fool you – Katheryn is actually three years older than him! These two were married for three years, from 1989 to 1991. In fact, the two directors were actually a pretty good match, but it was unexpected at the time.
Nowadays, people barely remember that these two were an item at one point. Since then, Cameron has been married and divorced from Linda Hamilton before he found his current wife, Suzy Amis. Bigalow, on the other hand, has been focused on work and hasn’t remarried.
Simon Cowell and Carmen Electra
While their relationship was on the shorter side, Carmen Electra did, in fact, have a thing with Simon Cowell for a while back in the day. It’s rather difficult for us to imagine these two together if we’re being honest.
Honestly, it’s hard for us to imagine Simon with anyone due to his sharp personality. Unless he critiques things like the way his partner eats dinner or snores at night – we would pay to see that! Who knows, maybe some people like that in a partner.
Tom Green and Drew Barrymore
We aren’t sure exactly why this one feels off, but something just doesn’t sit right with us. This relationship is the kind that time has forgotten. Way back in 2001, these two were married. Actually, it would be more accurate to say that they were married for half of 2001.
In July, they exchanged vows, and Tom filed for divorce before the year was up. We know that not every relationship works out, and that’s okay. At least they were able to make it work for a little while.
Ryan Reynolds and Kristen Johnston
Of course, Ryan Reynolds is now married to Blake Lively. They make a beautiful power couple and people simply adore their relationship. However, before all that happened, there was Ryan’s marriage to Scarlett Johannson, which everyone was obsessed with.
Well, even before that, Ryan was in a relationship with Kristen Johnson. This happened way back in 1999 if you didn’t get that from the outfits they are wearing in the picture. It was like a completely different world.
Michael Douglas and Diandra Luker
Michael Douglas is one actor that almost anyone would recognize. Recently, he appeared in the major hit movie, Avengers: Endgame. If you haven’t seen that, he also played in films like Wall Street.
Michael has been married to Catherine Zeta-Jones for quite a while now. Before that happened, he was marrying Diandra Luker. At the time, she was 19 and he was 33… But who’s counting? The two even had a child together.
Britney Spears and Colin Farrell
Yes, this is real. A little while ago, Britney Spears was dating Colin Farrell. It’s pretty wild when you think about it. We highly doubt that anyone could have predicted that these two would get together.
All the same, we have to admit that they make a cute couple. It was said to be a brief relationship, but it’s fun to think about how things would be if they stayed together. In any case, Britney is now living her best life, so it wasn’t meant to be!
Richard Gere and Cindy Crawford
We don’t doubt that Cindy Crawford is going to be stunning until the day she dies. Aside from that, she and Richard Gere used to actually be married! They were married for four years, as a matter of fact.
The most surprising part? Their age difference. Richard was 15 years older than Cindy. When they got together, she was 22 years old while he was 37. Still, they made it work for a while, but Cindy has claimed that their ages were the reason they separated.
Rihanna and Shia LeBeouf
This kind of goes against the rules of our list, but we simply had to talk about it! Are these two unexpected as a couple? We would definitely say yes. If someone told us now that these two were dating, we wouldn’t believe them.
Well, back in 2007, this made more sense. However, we are sort of breaking the rules since these two went on just one date, but we couldn’t help ourselves. It was too interesting not to mention it at all.
Nicolas Cage and Lisa Marie Presley
We know that Nicolas Cage does not need an introduction. The actor has starred in so many different popular movies. Still, did you know that he was once married to Lisa Marie Presley? If you don’t know who she is, think about her last name.
If you haven’t heard of the name, she really is Elvis Presley’s only daughter. She and Nicolas getting together is pretty wild, but the marriage didn’t last too long. Here’s a little fun fact for you: she was also married to Michael Jackson.
Jay-Z and Aaliyah
Here is one celebrity relationship that is mindblowing only because of Jay-Z’s marital status now. In case you didn’t know, Jay-Z is married to Beyonce now and the two have several children together.
Because of that, it’s difficult to imagine the rapper with anyone else. Still, we have to talk about how he once dated Aaliyah before her tragic passing. If they had stayed together, we have no doubt that they would have made a serious music power couple.
Madonna and Dennis Rodman
Madonna is someone with a rather colorful dating history. She’s been married a couple of times, once to Sean Penn and once to Guy Ritchie. Aside from that, there have been several interesting relationships. Perhaps the most intriguing one of them all was her relationship with basketball star, Dennis Rodman.
While it seems rather unlikely at first, the two are very over the tip. It’s clear that Madonna really liked him seeing that Dennis said she wanted to have a baby with him. So much so that she was actually willing to pay him! What?
Johnny Depp and Ellen Barkin
We don’t think it would be a stretch to say that most people remember Johnny Depp’s relationship with Kate Moss before they remember that he was dating Ellen Barkin at one point. The actress is mainly known for her roles in movies like Fear and Diner.
The two made a good looking couple, but the age difference was definitely there. At the time they were together, Ellen was 40 while Johnny was 30. Aside from that, we can’t get past the hair! Young Depp was such a heartbreaker.
Laura Dern and Ben Harper
There’st just something that feels so wholesome about this relationship. We can’t really explain what it is, but we like these two together. Unfortunately, this marriage ended back in 2013 after a total of eight years together.
Laura and Ben met at one of their concerts and ended up having two kids together over the span of their relationship. At the end of the day, it was Ben who filed for a divorce. It looks like they’re on good terms these days, which is good to hear.
Kirsten Dunst and Jesse Plemons
While Peggy and Ed Blumquist were high school sweethearts on the television show Fargo, we never expected they would start dating in real life! After Kirsten’s split from actor Garrett following a four-year relationship, the Spiderman actress started dating her Fargo co-star.
She and Jesse started dating and are still together! They welcomed their first child, a baby boy, in May 2018 and are now engaged but are in no rush to get married anytime soon. We’re just happy that they’re happy.
Christina Hendricks and Geoffrey Arend
Let’s be honest. Christina Hendricks is most likely the kind of person most men dream about. And yes, Madam Secretary actor Geoffrey Arend is cute, but he’s no match for the red-headed bombshell. As soon as these two met, Christina was taken by his energy. She said, “He was just charming, funny, and very magnetic.”
She even thought she scared him away when she spoke about having kids not long after they met, but it turns out that she didn’t. The couple got married in 2009 and ended up being married for a decade. Christina filed for divorce in 2019, but the two remain good friends.
Katharine McPhee and David Foster
When the record producer, David Foster, proposed to his girlfriend, singer Katherine McPhee, he was exactly twice her age. Since he’s now 70 at she’s 36-years-old, we aren’t surprised about all the raised eyebrows.
However, their love has since grown and blossomed. These two have no time for haters. Katherine has even spoken about how the last thing she showed her father before he passed away was her engagement ring. She couldn’t be happier that this was the last moment they shared.
Quentin Tarantino and Daniella Pick
With their 20-year age difference, Quentin Tarantino and Daniella Pick are yet another odd Hollywood couple. The director met the Israeli singer back in 2009, back when he was promoting his movie, Inglorious Bastards, in Israel.
While he’s known for violent movies, it turns out that Quentin is quite the romantic. Daniella spoke about him in an interview, saying, “He’s brilliant, romantic, funny, sensitive, and honest.” In June 2017, the couple got engaged and in 2018 got married. In February 2020, the couple welcomed their first child together.
James Goldstein and Amalie Wichmann
If you happen to be a fan of the Los Angeles Lakers, you probably know who James Goldstein is. The NBA super-fan seems to also be a millionaire, although his income source is still a mystery. He tends to be very secretive about that.
Other than going to games, James can be found spending time with his gorgeous models. Among them is the stunning Danish model, Amalie Wichmann. She’s, of course, decades younger than the millionaire. Even in his 70s, there must still be something about him the women love.
Sarah Paulson and Holland Taylor
Sarah came out as part of the LGBT community back in 2005. When she started going out with Holland Taylor, it took many people by surprise. The reason is that Sarah is 43 years old while Holland is 75 years old. People have even said to Sarah that this relationship might damage her career.
“When people found out I was with Holland, some said: ‘I think you have to be careful, I’m afraid it’s going to affect your career negatively,’” she said. While she admits that her choices are unconventional, she’ll just keep doing her own thing.