Unbelievable Celeb Couples That Had Fans Questioning Reality
Although so many people dream of becoming celebrities, it's easy to underestimate how much privacy the people in that otherwise privileged position have to sacrifice. Not only is someone always watching their every move, but every relationship they have is equal parts chronicled and judged.
Still, it's not impossible to see where the fascination comes from. Some couples just seem to make so much sense together that it can be jarring when the opposite type is spotted. When it seems like celebrities were thrown together at random, people get curious as to how it happened.
Avril Lavigne and Tyga
Avril Lavigne has a long history of dating fellow musicians, but it often wasn't hard to see what they had in common and what drew them to each other. However, it came as a complete surprise to the public in February of 2023 when she started appearing in intimate photos with former Young Money rapper Tyga.
Since they didn't discuss their relationship publicly, it was unclear how the spark that brought them together formed or what they generally had in common. However, it's possible that the couple ended up wondering this themselves, as People reported that they broke up that July. They seemed to stay on good terms, though.
Pete Davidson and Kim Kardashian
Even taking the seemingly inescapable drama with Kardashian's ex-husband Kanye West aside, there was little about this unusual matchup that inspired much faith that it was going to work out. Davidson may have established himself as a man with some impressive romantic charisma, but that can't patch over everything.
And while E! Online quoted Kardashian as describing Davidson as very communicative and loving; she said the long distance between them and the lack of time they could realistically share together led the couple to call it quits in May of 2023. It was also unclear how well Davidson's laid-back personality would mesh with Kardashian's hyper-regimented lifestyle.
Madonna and Guy Ritchie
Although both Madonna and Guy Ritchie had high-profile enough careers to make them a power couple in 2000, it always seemed like it would be tough to reconcile her glamorous aspirations with his "regular guy" (or regular bloke, in this case) mentality. The failure of Swept Away in 2002 demonstrated that the two weren't great professional collaborators either.
Although Ritchie told The New Zealand Herald that he doesn't regret this marriage after it ended in 2008, he did admit that it felt akin to stepping into a soap opera. In his words, "When you end up with a lot of the things you set out to chase and find that you've stumbled into all sorts of hollow victories, then you become deeply philosophical."
Macaulay Culkin and Mila Kunis
Although both Culkin and Kunis are former child stars, that didn't stop their relationship from seeming like it came out of nowhere when they were ready to discuss it in the mid-2000s. According to InStyle, part of what drew Culkin to Kunis was the fact that she was on Family Guy, which Culkin was a big fan of.
But while their relationship would eventually have a more solid foundation than that after their introduction in 2002, Kunis cited Culkin's unusually extreme fan attention as a factor in their breakup. She also expressed regret for the way she broke up with him in 2011, which went on to damage their platonic relationship after the fact.
Shaquille O'Neal and Nicole Alexander
When she dated Shaq in the early 2010s, Nicole Alexander had scored twin victories on the reality shows The Flavor Of Love and I Love Money. But while this points to a mismatch in levels of celebrity with the NBA legend, that wasn't what had people scratching their heads about this couple.
Instead, discourse largely centered around their perceived physical compatibility. While the list of people as tall as Shaq is admittedly a short one, the way they had to pretzel their bodies together to kiss left observers unconvinced they were going to work out. But to Alexander's credit, she proved on an episode of Jimmy Kimmel Live that she could lift him.
Isla Fisher and Sacha Baron Cohen
It's hard to explain why, but it often comes as quite a surprise to people when they first learn that Isla Fisher and Borat provocateur Sacha Baron Cohen are married. However, even a cursory look at their careers makes it clear that their sense of humor is a major aspect of their respective personalities.
And unsurprisingly, that's exactly what led them to hit it off. In a quote relayed by People about their first meeting, Cohen said, "She was hilarious. We were at a very pretentious party, and me and her bonded over taking the mick out of the other people in the party. I knew instantly. I don't know if she did." They have been together for over 20 years and married for over a decade.
Megan Fox and Machine Gun Kelly
Although some pairings inherently seem bewildering to outsiders, the problem that Megan Fox and rapper-turned-rocker Machine Gun Kelly's relationship had in the public eye concerned their erratic behavior once they got together. Between the tales of a painful engagement ring and blood-drinking rituals, nobody was quite sure what to make of this couple.
And as Harper's Bazaar noted, the fact that the couple kept breaking up and getting back together for cryptic reasons wasn't a sign of a healthy, lasting relationship either. Although it's unclear where exactly their relationship is after repeated attempts at an engagement, many fans of both celebrities aren't exactly confident it's going anywhere.
Will Smith and Jada Pinkett Smith
The relationship between Will Smith and Jada Pinkett Smith is odd in that it seemed perfectly normal to the public for many years after their 1997 nuptials. However, Vulture chronicled the seemingly rapid-fire series of revelations since the mid-2010s that has only made their relationship seem stranger with each one.
Pinkett Smith's infamous "entanglement" with R&B singer August Alsina was a big part of this controversy, but a microscope fell over the eccentricities of their marriage after Smith's widely-publicized "stunt" at the 2022 Academy Awards. Pinkett Smith has since revealed that the couple had secretly been separated since 2016, leaving fans with far more questions than answers.
Ted Danson and Whoopi Goldberg
Nowadays, it's not uncommon for people to forget that Ted Danson and Whoopi Goldberg were ever an item. But when they were, one piece of national news was so red-hot in its controversy that the public couldn't help but wonder what was going on in their relationship.
As Slate reported, this concerned a bewildering Friar's Club roast from 1993 that saw Danson make such a cringeworthy attempt to roast his then-girlfriend that the Friar's Club issued a rare apology shortly thereafter. Although Goldberg was steadfast in her defense of Danson after the fact, their relationship didn't outlive the controversy.
Ashley Graham and Justin Ervin
If Ashley Graham and Justin Ervin seemed like an unusual match when they first got together, Graham would have agreed with that sentiment after their first date. According to Yahoo! Entertainment, she wasn't impressed with his style when he approached her in an elevator at their church. She said, "With his short hair, ill-fitting, baggy Old Navy jeans, white Hanes T-shirt, and Converse sneakers, he exuded a major nerd factor."
She wasn't any more impressed when he left her with the bill after the date was over and deleted his number soon after. However, once they saw each other again and shared what she considered a productive and fulfilling conversation, she gave him another shot. They've now been together for over a decade.
Elon Musk and Grimes
Considering how many eccentricities they shared and their similar optimism about the future of technology, the relationship between tech mogul Elon Musk and independent musician Grimes seemed to make both too much and too little sense all at once.
But while their decision to name one of their children X Æ A-Xii was perhaps the biggest source of morbid curiosity about the couple among the public, political and personal differences between them seemed to lead to the collapse of their relationship. According to HuffPost, Grimes is now engaged in a custody lawsuit with Musk regarding their three children.
Sarah Paulson and Holland Taylor
Although age gaps are typically a major factor in what makes a celebrity couple seem strange to the public, Sarah Paulson and Holland Taylor's relationship serves as an extreme example of this phenomenon. That's because Taylor is 32 years older than Paulson.
According to Vanity Fair, the couple cited other differences in their levels of sociability and desire to care for multiple pets but said that they find joy in those differences. As for the age gap, Paulson said, "If anyone wants to spend any time thinking I'm strange for loving the most spectacular person on the planet, then that’s their problem. I’m doing just fine."
Katy Perry and Russell Brand
According to Business Insider, Katy Perry met Russell Brand on the set of the 2009 comedy Get Him To The Greek, where she was supposed to kiss him in a scene that ended up on the cutting room floor. Nonetheless, there were enough sparks between them that they would spontaneously wed early in the following year.
The pairing between the pop star and the controversial comedian seemed odd at the time and would only be confirmed as such when Brand abruptly broke up with her via text message on December 30, 2011. This happened just 14 months after their wedding day, and Perry said years later that she never heard from him again.
Hugh Jackman and Deborra-lee Furness
When Hugh Jackman first linked up with his now ex-wife of 27 years, Deborra-lee Furness, there was a lot working against him. Their 13-year age gap was a risk factor, and it didn't help that Furness seemed ready to break up early on in their relationship.
However, Jackman believed she was the one, and once they gave the relationship another shot, they ended up sharing almost three decades together. However, it seemed Furness's instincts weren't as far off as Jackman thought, as People reported the couple announced the end of their marriage in September 2023.
Jason Momoa and Lisa Bonet
Although Jason Momoa and Lisa Bonet were a deeply well-liked couple during their time together, the origin story behind their relationship is something that could only have happened in Hollywood. As People reported, their relationship fulfilled a lifelong dream for Momoa, as he said he fell in love with Bonet at the age of eight while watching The Cosby Show.
The two met at a jazz club in 2005, and two years later, they would welcome their first of two children into the world. All told, the couple was together for 16 years, five of which were spent married after a secret ceremony in 2017. They announced their breakup in January of 2022.
Neil Young and Daryl Hannah
Although both the rock star and the actress have the kind of edge that would make them seem like they'd get along, perhaps the oddest aspect of their marriage is its timing. Both had been well-known in their respective fields for decades, so what finally got them together? Well, as People reported, their bond was based on their shared passion for activism.
However, it also seemed that some of their friends were nonetheless as bewildered about their relationship as some of their fans before they married in 2018. Young said, "When we got together, even some of my good friends were negative about it, and I could never understand it."
Seal and Heidi Klum
When soulful singer-songwriter Seal and German model and businesswoman Heidi Klum were spotted together in 2004, their relationship seemed to come out of nowhere. From the couple's perspective, that was more or less what happened. According to InStyle, the two happened to cross paths in a New York hotel lobby after one of Seal's workouts, and the attraction was instant.
Their relationship was characterized by eccentricities like Klum finding out she was pregnant during their first date and Seal later proposing to her in an igloo he had built for the occasion. And that was also true during their marriage, as they celebrated their eight anniversaries with additional weddings. However, the marriage wasn't as happy as it appeared on the surface, and they divorced in 2012.
Gwen Stefani and Blake Shelton
By all accounts, Gwen Stefani and Blake Shelton are in the midst of a happy, loving marriage. However, the difference in their musical inspirations and general vibes as respective people nonetheless made their connection confusing to their fans. And in fairness, it's unlikely that they would've expected their relationship to start the way it did either.
According to Today, Stefani and Shelton happened to be at the tumultuous tail end of their respective marriages to Gavin Rossdale and Miranda Lambert when they first met. Their bonding over their struggles blossomed into a friendship that eventually turned romantic after their divorces were finalized in 2015. Stefani said, "I had this huge weight on me, and nobody but my parents and obviously everybody involved knew."
Billy Bob Thornton and Angelina Jolie
According to People, there was a great deal about Angelina Jolie's brief but eventful three-year marriage that both confused and fascinated the public in the early 2000s. Their sudden elopement a year after Thornton broke off an engagement with Laura Dern was part of it, as was the 20-year age gap between the two.
However, the most well-publicized aspect of their marriage came in 2001 after Thornton and Jolie were photographed wearing necklaces that contained vials of each other's blood. But while their marriage ended in 2003, Thornton said this had more to do with the differences in their preferred lifestyles than any of the eccentricities they shared along the way.
Julia Roberts and Lyle Lovett
Part of what made Julia Roberts' two-year marriage to Lyle Lovett so baffling to people was how sudden it was. InStyle said they had only dated for three weeks before their elopement. And while their split was apparently amicable, it wasn't clear what brought them together in the first place.
However, they answered that themselves by saying mutual friends introduced them and that Roberts was a fan of Lovett's music. However, the nature of their star-studded lives was such that they couldn't realistically spend much time together. The relationship didn't survive that reality.
Dolph Lungren and Grace Jones
In terms of their fitness and intensity, one would be hard-pressed to find a more congruent couple during the 1980s than Grace Jones and Dolph Lungren. But while they were both actors, they also seemed to run in significantly different circles.
After all, Jones's passions seemed to take her closer to the art and fashion worlds than the sporting and scientific interests of Lundgren. As Lungren told The Times, he considered his relationship with Jones more of a fling than a serious partnership.
Christina Hendricks and Geoffrey Arend
It didn't exactly help that one of these actors was significantly more famous than the other, but Christina Hendricks's marriage to Geoffrey Arend seemed to come so out of nowhere that fans wondered how they met in the first place. According to The Hollywood Reporter, Hendrick's Mad Men co-star Vincent Kartheiser was the one who first introduced them.
But while the pair hit it off enough to get married in 2009, they didn't turn out to have a lasting relationship. Granted, a ten-year marriage is decently substantial in Hollywood terms. Understandably, the fairly private couple was tight-lipped about what caused their split.
Cher and Gregg Allman
Although Cher's whirlwind romance with Southern rocker Gregg Allman was well-publicized when she spontaneously hopped on a jet to Las Vegas and married him in the summer of 1975, a history chronicled by Entertainment Weekly made it clear that their relationship was doomed from the start. Especially since their first marriage only lasted nine days.
This was due to Allman's substance issues at the time, but Cher's professional reconnection with ex-husband Sonny Bono, the fallout from the couple's failed album Two The Hard Way, and what Allman cited as her "paranoia" about his potential relapse all presented their own roadblocks. The pair would split up for good in 1977.
Mary-Kate Olsen and Olivier Sarkozy
Throughout Mary-Kate Olsen's eight-year relationship with French banker Olivier Sarkozy, the couple remained private enough that neither the tabloids nor the public at large were able to glean many details about the couple. Nonetheless, the pairing and their subsequent marriage in 2015 perplexed Olsen's fans due in large part to the 17-year age gap between them.
As People reported, the couple would end up facing irreconcilable differences in their preferred lifestyles, attitudes regarding their respective careers, and the potential for having children together. This led Olsen to petition for emergency divorce in 2020, and the couple would reach a settlement during the following year.
Jim Carter and Imelda Staunton
To the casual observer, there really isn't anything weird about this relationship. Both Jim Carter and Imelda Staunton are British actors who broke out in similar eras to similar acclaim and with the same penchant for prestigious, sophisticated work. However, it seems to be fans of their work who have the hardest time wrapping their heads around their relationship.
That's because if they had two fictional characters fall in love, the last two they would imagine would be Dolores Umbridge pairing up with Mr. Carson from Downton Abbey. But while that pairing may not work in fiction, it's resulted in a marriage that's lasted over 40 years in real life.
Norman Reedus and Diane Kruger
For fans of the elegant German actress, Diane Kruger's engagement to Norman Reedus seems like a case of opposites attracting. Although Reedus is certainly hunky, his mystique comes off as a little more scraggly and rugged than hers.
According to E! Online, Reedus had attempted to propose to Kruger a couple of times during a motorcycle trip in Savannah, Georgia, but unruly teenagers and a thunderstorm led him to abort both plans. However, the tearful proposal happened the next day after he asked their three-year-old daughter to bring him a boot that secretly had the ring inside it.
Nikki Cox and Bobcat Goldthwait
Although it seems she's largely retired from the spotlight, Nikki Cox was once an actress who ended up engaged to her Unhappily Ever After co-star Bobcat Goldthwait in 1997. Not only did they seem like entirely different people, but another risk factor in that relationship's health was the fact that at 19 years old, Cox was 16 years Goldthwait's junior.
In an interview with Atlanta Magazine, Goldthwait revealed that their relationship came to a sudden end when a hotel worker's indiscretion led him to discover that she was secretly seeing comedian Jay Mohr on the side. Cox would marry Mohr in 2006 before the two divorced in 2018.
Jeff Goldblum and Emilie Livingstone
From Hearst heiress Lydia Hearst-Shaw to Lost actress Tania Raymonde, Jeff Goldblum has a long history of dating women significantly younger than him. Specifically, Heart is 32 years Goldblum's junior, while Raymonde is 36 years younger than him.
But while these were fairly fleeting dalliances, Goldblum was also guided by this proclivity to pursue a relationship with Canadian dancer and former Olympic gymnast Emilie Livingston. Livingston is 31 years younger than the Jurassic Park actor, and they've been married since 2014.
Leonardo DiCaprio and Camila Morrone
Even before DiCaprio started dating Morrone, even casual observers noted the actor's pattern of seemingly dating women right up until they turned 25. And however it happened, his relationship with the actress and model didn't exactly break this pattern.
According to InStyle, the couple became official by the 2020 Academy Awards, and their 23-year age gap was quickly noted by the public. Although Morrone defended their relationship with a comparison to Humphrey Bogart and Lauren Bacall's age gap, the two nonetheless broke up in August 2022. She had turned 25 two months earlier.
Jack Harlow and Dua Lipa
Although it's hardly unusual for musicians to date each other, the story of how Dua Lipa and Jack Harlow came to be romantically linked is an odd one. As Vulture reported, the Kentucky rapper included a song named after her on his 2022 album Come Home The Kids Miss You, in which he rapped, "I'm tryna do more with her than do a feature."
But while the London-born singer described it as not her kind of song at the time, it seemed that Harlow's wish nonetheless came true as the two reportedly dated in 2022. It appears that Harlow wasn't just casually rhyming when he wrote that song.
Janet Jackson and Matthew McConaughey
Due to some intimate-looking appearances together during the 2000s, persistent rumors abounded that Matthew McConaughey was dating Janet Jackson. But while both parties were coy about this for a long time, The New Zealand Herald reported that McConaughey finally confirmed the rumors during an appearance on Watch What Happens Live with Andy Cohen.
However, it seems their fling was much more short-lived than people suspected. That's because after he laughed for a moment at the question, McConaughey finally answered, "We went and had dinner one night. That was sort of it." It may not be the most climactic answer, but that's his story, and he's sticking to it.
Tom Cruise and Cher
Although Cher has had her share of relationships with other celebrities, one of the most often forgotten and seemingly random among them was her short period dating Tom Cruise. According to Entertainment Tonight, they first met at Madonna and Sean Penn's wedding in 1985, but the spark didn't form between them until their second meeting.
It was at a White House event that they started to bond. According to Cher, "A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic. We didn't go out till way later, but there definitely was a connection there."
Flavor Flav and Brigitte Nielsen
When founding Public Enemy member Flavor Flav and Danish actress and model Brigitte Nielsen appeared together on The Surreal Life, they grew closer than anyone expected. When their romance budded on the show, it came so far out of left field that it inspired a separate reality show called Strange Love.
But while their relationship was short-lived, and People reported they hadn't seen each other for over a decade, Flavor Flav remains an enthusiastic supporter of her accomplishments in life. As he said, "All I want to see is her happy and everything she wants in life. All she wants in life is a happy life and good family life. She's good to people. That's why we clicked. Birds of a feather will flock together."
Chelsea Peretti and Jordan Peele
Although acclaimed director Jordan Peele and actress Chelsea Peretti have been married since 2016, the circumstances that led their relationship to blossom are a little unorthodox by Hollywood standards. Rather than meeting at a party or through mutual friends, they met on Twitter.
As Peretti told Entertainment Weekly, "He was very complimentary of the Web series I once did. We were gonna go to Sizzler on our first..." According to People, the two eloped to the Big Sur with only their dog as a witness after dating for two years.
Olivia Wilde and Harry Styles
Although Olivia Wilde's nearly two-year relationship with pop star Harry Styles inherently came out of nowhere for the public, it also appeared to be a victim of some truly unfortunate timing. According to People, part of the problem was that their romance blossomed amid Wilde's messy divorce with Ted Lasso star Jason Sudeikis.
What also didn't help was how intertwined their relationship was with the troubled production of Wilde's movie Don't Worry Darling, which Styles co-starred in after replacing Shia LaBeouf. The pair would "take a break" from their relationship in November 2022.
Travis Barker and Kourtney Kardashian
Although Travis Barker's musical stylings didn't always represent the most hardcore expressions of the punk ethos, it nonetheless came as a surprise to both his and Kourtney Kardashian's fanbases when they became an item. But as People reported, they had already known each other for years when they started dating in 2021.
Curiously, they celebrated their union with three separate weddings in 2022 before hinting at a fourth in November of 2023. While the reason for these multiple ceremonies is unclear, that month also saw the couple welcome their first child together.
Bethenny Frankel and Eric Stonestreet
According to Page Six, Real Housewives Of New York star Bethenny Frankel addressed rumors that she and Modern Family actor Eric Stonestreet were dating during an appearance on Watch What Happens Live. And while the two maintain that they share a platonic friendship now, they admitted that this wasn't always the case.
As Stonestreet put it while speaking to Andy Cohen, "I think we decided that we make much better friends, but she's a wonderful kisser." Although the two were barely aware of who each other was when they first met, they became fast friends.
Jamie Foxx and Katie Holmes
Although they had had a long-term romance, the most curious aspect of Katie Holmes's relationship with Hollywood Renaissance man Jamie Foxx was that half of it had already elapsed by the time it was confirmed to exist. As People reported, the pair had deflected dating rumors until music industry titan Clive Davis effectively exposed their relationship during his Pre-Grammy Awards Gala in early 2018.
By 2019, Holmes and Foxx would appear more openly as a couple but largely kept their relationship more or less under the radar until they split for just as private reasons in 2022. By that point, they had been dating for six years.
Shailene Woodley and Aaron Rodgers
Until 2021, Shailene Woodley and NFL quarterback Aaron Rodgers were so coy about their relationship that even their engagement had been kept a secret. But when Woodley opened up about it, she admitted that she never would've imagined the relationship until it happened. She also said that Rodgers was more of a "nerd" than his profession suggested.
In a quote obtained by Vanity Fair, she said, "I never thought I'd be engaged with somebody who threw balls for a living. Like, I never thought as a little girl, 'Yeah, when I grow up, I'm gonna marry someone who throws balls! Yeah!' But he's really just so good at it."
Michael Jackson and Lisa Marie Presley
During some of the most tumultuous years of Michael Jackson's life, Entertainment Weekly reported that he secretly married Elvis Presley's daughter, Lisa Marie, in 1994. Due to the whirlwind nature of their romance, public confidence in the relationship was low.
Jackson acknowledged this by saying, "And just think, nobody thought this would last" when the couple opened the 1994 MTV Video Music Awards together. However, it turned out that he would be tempting fate with this statement, as the pair divorced in 1996. Although they cited irreconcilable differences, Presley later said that they dated off and on over the following four years.
