Unexpected Celeb Couples: 35+ Pairings That Caught Us Off Guard

It’s not that we have anything against these celebrities, but seeing as we have known some of them for quite a while, we thought we knew the kind of people they tend to be attracted to. Their ‘type,’ if you will. However, we were proved wrong.

Celeb romances are the stuff of movies. Literally. That’s why at some point in Hollywood, it wasn’t surprising to hear that two co-stars had fake-dated to promote a movie or two. That said, we don’t choose who we love, so even if some of these pairings look odd, we like to believe they really were in love.

So, if you’re a lover of love and pop culture, we assure you this will be a fun way to spend the next few minutes. From Cher and Tom Cruise to Bill Murray and Kelis, join us as we gasp and aaaw, at these unusual celeb couples!

Harry Styles and Olivia Wilde

This romance and the drama that unfolded as a result of its existence will go down in history. First of all, no one would have ever predicted that Olivia and Harry would date. Yes, there is the 10-year age gap, but that wasn’t the only reason people felt blindsided. Anyway, now comes the drama.

Harry famously starred in Olivia’s directorial debut, Don’t Worry Darling, where they fell in love. The film’s press tour was filled with reports of feuds among the stars, especially Olivia and Florence Pugh, the Shia LaBeouf scandal, and the infamous Spitgate. The two eventually split towards the end of 2022.

Clare Grant and Seth Green

Seth Grant met the love of his life, Clare Grant while handing out autographs at a comic book event in 2007. She was the photographer at the event. However, it was only after their second meeting at Comic-Con that they became close friends.

As friends typically do, they started hanging out together often, and this quickly led to a romantic relationship. As the rest of the world prepared for the New Year of 2010, Seth got down on one knee and proposed to Clare. They got married five months later and have been together ever since.

Angelina Jolie and Billie Bob Thornton

Before she became part of the iconic couple that was Brangelina, Angelina Jolie used to be with actor Thornton. Though their relationship raised eyebrows due to their 20-year age gap, they fell in love while doing a film together and were married for about two years.

Many people don’t know this, but Angelina was his fifth wife! Though Bob remembers their time together fondly, he confessed that their marriage could last because the two of them had very different lifestyles. That said, they are still good friends.

Ariana Grande and Ethan Slater

This one was a complete and utter shock to everyone. Ariana Grande has had quite a number of famous romances, but when she finally got married, she picked someone who wasn’t a celeb: Dalton Gomez. We were shocked but quickly recovered because they were so cute together. Sadly, they didn’t last.

July 2023 came along with news of separation and divorce and that Ari was seeing fellow actor and singer Ethan Slater. This was considered especially scandalous since they were both married to other people. However, they maintain that they only started dating after they’d been separated from their spouses. They’re currently living together in NYC.

Kim Kardashian and Pete Davidson

Speaking of Pete, he and Kim Kardashian famously made all our jaws drop in 2021 when they confirmed they were dating. It started with a seemingly innocent kiss during an episode of SNL, but soon enough, the world was reeling from news of a possible serious relationship.

Pete and Kim were absolutely adorable together. And seeing as it’s the Kardashians, Pete also made appearances on their popular show as well as multiple red-carpet events. However, that put him in Ye’s cross hairs as you might recall. The pair sadly ended things after nine months.

Tom Cruise and Cher

Cher is a queen in her own right. When she met Tom Cruise in the mid-eighties, she was 38 and had already been ruling the airwaves for about two decades. On the other hand, Tom was only 23 and had just begun to make a name for himself.

The two stars met at Madonna’s wedding. However, they didn’t really start anything until after they met the second time at The White House. Though the relationship didn’t last, it was apparently quite amazing while it lasted, seeing as Cher says that Tom is among her Top five lovers. Quite the achievement, we’d say!

Simon Halls and Matt Bomer

After he played a con agent on the TV show White Collar, Matt Bomer was all the rave among womankind worldwide. Well, you can’t really blame us after peeping at his baby blues and gorgeous auburn hair that curls up perfectly and rests by his temples.

Sadly, we all learned he was not single. Matt and his husband, Simon Halls, have been together for over a decade. Though the two are extremely private, we know that they got married in 2011 (though they only told the world in 2014), share three sons together, and look absolutely yummy in selfies!

Mary-Kate Olsen and Olivier Sarkozy

When we hear the name ‘Olsen,’ a brief image of two wide-eyed, pig-tailed blonde twins comes to mind. Mary-Kate and Ashley got into Hollywood before they were a year old and have since made a name for themselves both in that space and the fashion industry.

Though they both left Tinseltown and are relatively private, it’s fairly common knowledge that Mary-Kate met and fell in love with banker Olivier Sarkozy in 2012. Though the relationship raised eyebrows because he was 17 years her senior, they got married in 2015 and enjoyed well over five years together before divorcing in 2021.

Taylor Swift and Travis Kelce

The world just can’t get enough of Taylor and her romances. Just when we think we have her type down to a T, she proves us wrong. Travis Kelce and her immediate ex, Joe Alwyn, couldn’t be more different. But so far, things seem to be going well for these lovebirds.

After sparking dating rumors in September and seemingly confirming them the following month, Taylor has been painting the town (well, football stadiums) Red as she supports her man. Travis is also quite the supportive boyfriend as he’s been spotted at several of her shows. It seemed weird at first, but now we kinda like them!

Chelsea Handler and 50 Cent

We can hardly believe this too. Some men would easily be scathed by Chelsea Handler’s wicked sense of humor, but 50 is not one of them! Chelsea has always been very open about her life, so their 2011 relationship, though short-lived, has always been public knowledge.

The comedian said she liked how masculine 50 Cent was, which we 100% get! She also described him as fun to be around and even calls him her favorite ex. Though the reason behind their breakup is a mystery, Chlesea maintains that it was a casual thing, so maybe it just died a natural death.

Wladimir Klitschko and Hayden Panettiere

You often hear about romances that get hate because of a significant age difference. Well, these two are proof that height is not an issue either. Wladimir Klitschko and Hayden Panettiere met and hit it off in 2009 and spent most of the following decade in and out of each other’s lives.

After that meeting, they started dating on and off until the Ukrainian boxer proposed to the actress in 2013. Sadly, the engagement had to be put on hold but the couple later announced that they were expecting. Though they eventually broke up for good, they still share a close friendship and a daughter.

Mariah Carey and Nick Cannon

To us, Nick Cannon was always that guy we knew from Nickelodeon. But that all changed when he met Mariah Carey, who had already made a name for herself in the musical industry. Unfortunately, the 39-year-old comedian no longer believes in marriage after his divorce from Carey.

That said, when things between these two were good, they were really good. They started dating in 2008 and got married two months later. Nick proposed twice, and the couple got married in the Bahamas, renewed their vows each year they were together, and were blessed with two beautiful twins. See what we mean?

Katie Holmes and Tom Cruise

Do you remember Tom Cruise jumping up and down Oprah’s couch, claiming that he was crazy in love and saying his girl was extraordinary? Well, at that point, we believed nothing would break he and Katie Holmes apart. Forget Brangelina; TomKat was the name out there.

Theirs was a quick coupling. After Katie casually mentioned that she always thought she’d get married to Tom Cruise, the two were spotted together in Rome barely six months later, in April 2005. Three months later, they were engaged. They got married the following year and stayed together for six more years before they split.

Pete Davidson and Ariana Grande

Pete and Ariana reportedly got together in the spring of 2018, and just a few short weeks later, they were making headlines everywhere with enviable milestones like themed ‘His $ Hers’ tattoos, adopting a pet together, and most shocking of all, an engagement.

Pete asked to marry the pop star after just a few weeks of dating, and she said yes. Sadly, everything came crumbling down in October when they sadly broke up. In addition to things going a little too fast, their rough patch was exacerbated in part due to the death of Ari’s ex, Mac Miller.

Amber Tamblyn and David Cross

This Sisterhood of the Traveling Pants star is an outspoken feminist who found her match in comedian David Cross. These two have been together for over fifteen years and have been married for over a decade. Like many other couples on our list, they share a significant age difference.

She is forty while he is fifty-nine. Despite that, they have managed to build a beautiful home for themselves and their daughter. According to them, the secret ingredient to their lasting relationship is effort and couples therapy. Hats off to them.

Katie Holmes and Jamie Foxx

While TomKat was certainly Katie Holmes’ most famous relationship with an A-list actor, it wasn’t her only one. Before they broke up in 2019, she and Jamie Foxx dated for about six years. News of their relationship came as a shock because Foxx and the actress’ ex, Tom Cruise, were good friends.

That said, they were extremely lowkey about their affairs because even though they were first linked together in 2013, it wasn’t until 2018 that they went public. Additionally, they rarely ever did red-carpet appearances together. We hope they both find love and happiness.

Sarah Paulson and Holland Taylor

This couple has an age gap of 32 years! When asked if this disparity caused troubles at home, Sarah Paulson claimed that it was because of this that they’ve appreciated what little time they have together. She and Holland Taylor first met in the mid-2000s but didn’t start dating until 2015.

All it took was a DM from Taylor to spark the flame. The two were “blindsided” by people’s reactions around the world. As you’d expect, some people were extremely hateful, while others were very supportive and happy for them. So far, the couple seems to be doing a wonderful job of ignoring the first half.

Taika Waititi and Rita Ora

No one likes a funny pose more than these two, and that’s why we absolutely adore them! Rita Ora and Taika Waititi reportedly met sometime in 2018. But it wasn’t until about three years later, in April 2021, that people started speculating that they could be more than friends.

A few months after that, they made their red carpet debut, and we finally got our answer. It may have seemed random at first but the two stars have proved that theirs is a true love story. They have been husband and wife for close to two years now.

Kate Beckinsale and Pete Davidson

And here we thought only men had fun with much younger women. Kudos to Beckinsale for landing a guy 20 years her junior! In early 2019, she and Pete were spotted flirting during the Golden Globes after-party. Within three months, they shocked everyone with a public display of smooches during a Rangers hockey game.

Though many were disappointed with Beckinsale’s dating choice, they both had a way of handling it, especially Kate, who always had just the right comments for haters on her Instagram. Sadly, the two didn’t last very long, as by April of that same year, they were done.

Renée Zellweger and Jack White

An actress and a rockstar make for quite the exciting couple. Renee and Jack White met while filming the 2003 movie Cold Mountain. Although she had always been private about their relationship, we still got a few glimpses of them, including an attendance at the Oscars during the year and a half they were together.

Before White, the actress had been dating Jim Carrey. The two actors even got engaged, but sadly, they split up before jumping the broom. Since 2021, Renee has been in a loving relationship with Ant Anstead, who also works in the industry. So far, things seem to be going well.

Cynthia Nixon and Christine Marinoni

Sex and the City fans will recognize one of these ladies as Miranda Hobbes. Though most people don’t know, Cynthia Nixon has been married to her wife, Christine Marinoni, for about twelve years now. Before Christine, Cynthia had never dated women, which explains why she’s here.

When describing their relationship, the actress said that after meeting and becoming friends with Christine in the early 2000s, she fell in love and simply couldn’t let her pass by. Today, they share three kids and are still going strong.

Jesse James and Sandra Bullock

These two seemed to have it going when they appeared at the Academy Awards in 2010. Sandra was all smiles and radiant, aglow with her man and an Oscar win. So when their divorce became public, we were all taken aback. What had happened?

Well, the two met in December 2003 and got married about a year and a half later. Everything seemed to be going well and they even later adopted a child together. Sadly, it’s rumored that Jesse was unfaithful to the actress, and she simply couldn’t get past that.

Selena Gomez and Benny Blanco

This relationship has to be our favorite of 2023. Selena and Benny Blanco have been friends for years. Well, technically, he was friends with Justin Bieber first but they later all became friends. Benny has also produced multiple Selena Gomez singles, so they have known each other for quite a while.

The two musicians sparked dating rumors towards the end of 2023, but Selena only confirmed in December. The reason why their relationship was shocking is that Benny seemingly threw shade at Selena in 2020. However, she has fiercely defended her choice to date him and they are seemingly living it up by each other’s side.

Kelsey Henson and Hafþór Júlíus Björnsson

Yeap, that is The Mountain from GoT, and the girl next to him is his wife. The two met when he was filming Game of Thrones in Canada. She was working as a waitress at an establishment he went to and she requested an autograph.

They say don’t meet your heroes, but according to this story, you probably should because they could end up being the love of your life! Their size difference is always fascinating to witness, but they make it work. According to Kelsey, this sometimes means being picked up for smooches which we’re totally not jealous of.

John Mulaney and Olivia Munn

Though the timeline of their relationship has been marred with negative speculations, John Mulaney and Olivia Munn are still going strong today. According to them, they met in 2015 but didn’t get together until a few years later, mainly because John was still married to his ex.

They became official in May 2021, and by September, they had announced that they were expecting a baby. Thanks to Olivia, we have been treated to numerous yummy photos of the little one who turned two in November 2023. Recently, they were spotted looking smitten and drop-dead-gorgeous at the Oscars.

Ashton Kutcher and Demi Moore

These two are another couple that shook pop culture when they became official. Don’t get us wrong, Demi Moore is absolutely stunning. She is among that group of beautiful stars who, despite being in the industry for several decades, never seem to age.

The two had a fifteen-year age gap between them when they got married in 2005. Ashton went from living as a bachelor with a roommate to being married to a woman with three daughters. Quite the transitions. Unfortunately, they divorced after six years.

Kylie Jenner and Timothée Chalamet

2023 began with news about Kylie Jenner and Travis Scott being over for good. These two have been in an on-again-off-again relationship for years, so it wasn’t really a big deal. However, things got juicy when rumors about Kylie and our fave Timothée Chalamet being a thing started flying.

It started with the two stars being spotted at a show in Paris and speculations of attending Coachella together. After a few months, they were full-on smooching at events, and Kylie even made a cute picture of them her lock screen, so we got our confirmation. As far as we know, they’re still together.

Cameron Diaz and Benji Madden

America’s girl-next-door Cameron Diaz found her forever love in Benji Madden. They met in 2014 during a party hosted by the actress. He got an invite thanks to his twin brother, who’s married to Nicole Richie. A year later they got married in Cameron’s Los Angeles home with only 100 guests to stand witness.

This was less than a year after they had started dating. Recently, the two were blessed with a daughter. When asked why they think their relationship works, Cameron stated that they simply have the same set of values. She finally found her person.

Kat Dennings and Josh Groban

There is nothing 2 Broke Girls star Kat Dennings is short on. When she began dating Josh Groban, she became the envy of almost every woman. They went public with their relationship when they graced the Beverly Hills Carousel of Hope ball. That was the first time she heard him sing live.

The two got to know each other through Kat’s co-star Beth Behrs. That happened in 2014, and soon after, the pair was inseparable for the two years that followed. The pair have been very private about their split, but sources state that it was mutual, and they’re still friends.

Kendall Jenner and Bad Bunny

Much like her sister’s relationship with Timmy, Kendall Jenner dating Bad Bunny was a surprise to fans. The two were reportedly introduced to each other by friends, and soon after, they were spotted packing some PDA in a club in LA.

This was followed by citings at multiple events like Coachella and fashion shows. When asked about the relationship, they have both been very keen to insist they’d prefer to keep things private. Though it’s speculated that they broke up towards the end of 2023, they were reportedly seen together as recently as last month.

Matthew Lawrence and Chilli Thomas

Don’t you just love it when a romance, especially between stars, begins with a meet-cute? Matthew Lawrence and Chilli met thanks to a snowstorm that led to Matthew getting a last-minute flight on the plane Chilli was on. Their spontaneous ‘hello’ before the snowstorm led to a wonderful conversation during the flight.

And that eventually turned to them keeping in touch, getting to know each other long-distance, and eventually forming a friendship that turned into something more. That was back in 2022 and according to Matthew, he hopes to put a ring on it someday soon!

Shaquille O’Neal and Nicole ‘Hoopz’ Alexander

Although the pair have split, Nicole remains hopeful for herself and for Shaq. Despite the obvious height difference, they seemed largely compatible. They started their relationship sometime in 2010, and to the outside eye, it seemed that everything was going smoothly.

But they split up in 2012 after a heated argument that ended with Shaq breaking things off and asking Hoopz to leave the home they shared. Speaking in an interview a couple of years later, the reality star seemed to have moved on and rebuilt her life as she even said nice things about Shaq.

Emily Ratjkowski and Eric Andre

Is there a harder relationship launch than a cheeky, semi-nude Instagram post on V-Day? We think not. EmRata and Eric Andre may sound like an odd pairing, but they really happened back in 2023. Though they barely lasted two months, we can’t forget their highlights.

This relationship came a couple of weeks after the model broke up with yet another comedian, Pete Davidson. We really can’t blame her; these funny guys are very dangerous. One minute you’re laughing at an innocent joke, and the next, you are offering to cook for them!

Seth MacFarlane and Amanda Bynes

They have a 12-year age difference, but that didn’t stop them from testing the waters. We’re guessing they hit it off because they both have a wicked sense of humor. She starred in Nickelodeon’s All That and The Amanda Show, and he produced and voices several characters on Family Guy.

Amanda was shortly on Family Guy in 2008, which is speculated to be the time they met and started their short-lived relationship. How did the public discover that they were dating? They were seen at an LA party. To date, not much is known about this dalliance.

Brody Jenner and Avril Lavigne

They’re both strikingly attractive, but that wasn’t enough to keep the relationship going. Avril Lavigne and the Kardashians’ stepbrother met and started dating in 2010. For two years, they lived it up, traveling the world and having fun dates in clubs and other establishments.

They famously got four ‘His & Hers’ tattoos while they were together, and yes, one of those included inking each other’s names on their bodies. Sadly, things didn’t work out in the end, as Brody felt that he needed space to get back to his career.

David Spade and Julie Bowen

Julie Bowen first gained attention by appearing in soap operas, while David Spade made a name for himself by making us laugh. These days, Julie is quite a famous face thanks to her role as Claire Dunphy on Modern Family. But this particular relationship happened years before that.

Their relationship lasted less than a year after they became official in 2002. The pretty blondes are still close to date, though. Speaking about their time together, Julie said that many people in her life didn’t understand her attraction towards him, but like many of us, she loves herself a funny man!

Matthew Paetz and Lea Michele

Lea and Matthew Paetz split right around the time the honeymoon phase ended. They were set to be engaged around the time of the split, so friends and family were shocked that it happened. The two got together in 2014 during a music video shoot.

Lea had just lost her former boyfriend, Cory Monteith, and according to her, Matthew helped put a smile back on her face. Though some friends and family didn’t approve of their relationship because of Matthew’s past, she chose to give him a chance. They dated for two years before he ended things.

Jamie Cullum and Sophie Dahl

Next, we have another pair that has remained married! Yes, there’s an obvious six-inch difference between the two, but you know what women say about short lovers — they make up for it in every other aspect! Jamie Cullum describes Sophie as a “cool woman” and says that they “had a very immediate connection.”

They have now been married for fourteen years, and though they keep their lives relatively private, you can tell that they are genuinely happy from the brief glimpses we get. Judging by this list and the couples who are still together, privacy goes a long way, wouldn’t you agree?

Billy Corgan and Tila Tequila

This wild match was allegedly a reality in 2009. Tila Tequila was on the rise as a sultry bisexual on the reality show A Shot At Love With Tila Tequila, and apparently, the Smashing Pumpkins lead singer wanted to down her. Well, we can’t really blame him.

People assumed this relationship was a stunt because Billy’s band, Smashing Pumpkins, was on a decline. But we will never really know. That said, we know he’s dated several celebs like Courtney Love and Jessica Simpson so maybe it really happened.

Christina Hendricks and Geoffrey Arend

Christina and Geoffrey Arend married in 2009, but they had been dating for around three years prior to tying the knot. They had met two years before that and, by all intents and purposes, seemed so in love and happy to be together.

Sadly, divorce came calling in 2019. According to their statement on that development, they were both keen on rediscovering themselves during the transition. Christina said she was willing to work with him in the future…to raise their two beautiful dogs, which made up the rest of the family.

Ashley Olsen and Richard Sachs

This Olsen twin dated financier and art dealer Richard Sachs, who was 28 years her senior. They were seen on double dates with Mary-Kate and her hubby at Madison Square Garden. While people described Ashley and her beau as romantic towards each other, Ashley was also linked to George Condo during this time.

Though some people may find this odd, Ashley has dated older men before. Her partners have been 17-19 years older than her, so though Sachs was significantly older, it wasn’t her first time in such a dynamic. Though they undoubtedly had a wonderful time, they broke up after five months.

Ryan Gosling and Sandra Bullock

We just found out about this one, too! Despite their 16-year age gap, Sandra Bullock and Ryan Gosling quietly dated for about two years in the early 2000s after meeting on the set of a film they were doing together.

Since their breakup in 2003, both stars have had nothing but good things to say about each other and their time together. In fact, Gosling called Bullock one of her greatest loves. As fans of both stars, this ultimately made our day!

Bill Murray and Kellis

Who says summer romances are only for young adults and characters in period novels? Bill Murray and Kelis raised everyone’s eyebrows when they became the center of dating rumors. Aside from seemingly being two completely different people, fans also couldn’t get past their 28-year age gap.

Bill was spotted at one of the singer’s concerts in June 2023 which led to people asking all sorts of questions. However, as you would expect, none of them ever confirmed or denied anything. After two months, they reportedly ended things.

Rihanna and Shia LaBeouf

Relax, it was only “one date.” Seeing as she is one of the most beautiful and successful stars in the world, Rihanna has had her fair share of famous romances, both confirmed and rumored. Shia LaBeouf, on his part, is quite private, so we see why this one might come as a shock to some.

But it’s true. RiRi and the actor went on a date in 2007 after connecting via text. Sadly, that was all there was between them as, by Shia’s admission, there wasn’t a spark. Happens to stars, too. That said, the two are still cordial.

Ye and Irina Shayk

After Kim and Kanye called it quits, the rapper dated quite a few personalities before he finally met and married his current wife, Bianca Censori. One of those happens to be the famous model Irina Shayk, who was rumored to be dating Ye in 2021.

That said, OG Kanye fans may remember that she starred in one of his music videos (Power) in 2010. Apparently, they had a fling right around this time, but he later started dating Kim. After KimYe ended, Ye and the model reportedly spent his 44th birthday together in France.