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29+ Unexpected Couples in Hollywood Over the Years

Manny Ray Celebs /
Val, Amber Rose, Couple
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Remember when Ciara & Bow Wow were a thing? Or how about when Lil Wayne dated Beyoncé's sister? Don't worry, neither did we. Hang on while we rehash some of Hollywood's most surprising couples that left us scratching our heads...

Drake & Serena Williams

It's no secret he wears his heart on his sleeve. But that doesn't make Drake's former fling with Serena Williams any less shocking. That's right: Back in 2011, the tennis star caught Drizzy in his feelings.

Drake, Serena Williams, DatedDrake, Serena Williams, Dated
Chris Trotman via Getty Images

The rumors first started when Drake was spotted cheering on Williams courtside. But his 2013 track, Worst Behaviour, soon set things straight. "Tennis matches at the crib.... swear I could beat Serena," he rapped of their time together. And while they never confirmed their fling, the PDA-filled dates that followed said otherwise.

Matthew McConaughey & Janet Jackson

Safe to say, most of us wouldn't place an electric-dance artist and a small-town boy from Texas together. But back in the '00s, that's exactly what happened, as Matthew McConaughey first crossed paths with the global pop star. As for what happened next?

Janet Jackson, Matthew McConaugheyJanet Jackson, Matthew McConaughey
Frank Micelotta/ImageDirect via Getty Images

Perhaps not much. "We went and had dinner one night. That was sorta it," the actor revealed on Watch What Happens Live. In fact, "it was just for a minute, that's why I am so hesitant to mention it," as Janet put it. But while their fling may have lasted a hot second, we'll never be able to erase this one from our memory...

Pete Davidson & Kate Beckinsale

We thought Pete Davidson's adventures with Ariana Grande were the most confusing... until we watched him step out with Kate Beckinsale. Sure, there were no engagements or matching ink this time around. But their months-long fling took us on one whirlwind of a ride, and then some.

Kate Beckinsale, Pete DavidsonKate Beckinsale, Pete Davidson
JD Images via Shutterstock

And we're not the only ones. "It's all quite shocking and something to get used to," Beckinsale herself confessed of her former flame. From their 20-year age gap to their PDA-filled outings, she and the SNL star were hands down the most unexpected couple to come from 2019. Or so we thought. Keep scrolling...

Katie Holmes & Jamie Foxx

On paper, Dawson Creek's sweetheart and the outspoken comedian don't quite seem to go hand in hand. But despite the 11-year age gap, the unexpected duo did exactly that as they arrived at the Met Gala hand in hand back in 2019. Though it didn't last long.

Jamie Foxx, Katie HolmesJamie Foxx, Katie Holmes
Kevin Mazur/MG19 via Getty Images for The Met Museum/Vogue

After keeping their 6-year fling super private, the couple went on to officially call it quits by August. And while we can't say what exactly went wrong, their confusing romance will forever haunt us with endless questions. In the meantime, keep scrolling...

Brenda Song & Macaulay Culkin

On paper, two child-stars falling for one another sounds nice - perhaps even expected. But let's just say no one was ready for the bombshell that was Macaulay Culkin and Brenda Song's relationship. Even director Seth Green "didn't see that one coming" after casting them to star in his drama, Changeland together.

Macaulay Culkin, unexpected relationship  Macaulay Culkin, unexpected relationship
Kevin Mazur via Getty Images for Stand Up To Cancer

But that's exactly what happened after the co-stars stepped out together months later. Fast forward to today, and the unexpected duo have since welcomed their very own family. "My unicorn that I never thought could exist, I am luckiest person in the world because I am loved by you," Song gushed of the Home Alone star.

Tom Cruise & Cher

First it was Sony & Cher. Then it was... Tom Cruise & Cher? Yep, we also never saw that one coming. But back in 1985, as the Risky Business actor and the singer crossed paths at Madonna and Sean Penn's wedding, fate had other plans. And from the sounds of it? Their chemistry was actually unbelievable.

Tom Cruise, Cher, CoupleTom Cruise, Cher, Couple
Trippett/Sipa/Shutterstock

"I was so crazy about him. He was so wonderful," Cher admitted of her ex, whom she proudly dubbed one of her "top five lovers." (TMI, btw.) Despite the 16-year age gap, a then 38-year-old Cher and 23-year-old Cruise went on to date for months. And suddenly we'll never be able to unsee this…

50 Cent & Chelsea Handler

We get it. Fiddy might not exactly scream "romantic," - but if you ask Chelsea Handler? He's actually a "big fat teddy bear." Back in 2010, after landing a spot on the Chelsea Lately stage, the smitten rapper went above and beyond to make Chelsea his girl. And he clearly knew what he was doing.

50 Cent, Chelsea Handler50 Cent, Chelsea Handler
Twitter via @chelseahandler

No, there were no candy shops involved. Instead? The Candy Shop artist hit up his local florist: "He started sending me flowers - but ridiculous amounts of like 50 white roses," Handler admitted. Sure enough, the two went on to date for months before eventually calling it quits. But don't worry, there are no hard feelings here.

Madonna & Michael Jackson

Perhaps it's no surprise that the King and Queen of Pop's night out on the town back in '91 led to utter mayhem. But as far as the Hollywood royals were concerned? They barely gave their Oscars date much thought. "Michael was like, 'Who are you gonna go with?' I looked at him and said, 'I don't know... wanna go?'" Madonna revealed.

Michael Jackson, Madonna, DateMichael Jackson, Madonna, Date
Ron Galella Collection via Getty Images

As for the events that followed? Perhaps we'll never know. "You wanna know what happened after that? I'm not gonna tell you," the Like a Virgin artist teased. Lucky for us, decades later, she let it slip during an episode of Carpool Karaoke that she and MJ had locked lips. "Best date ever," she confessed.

Kim Kardashian & Nick Cannon

Long before her path led her to a Christian Genius Billionaire, 'Ye's soon to be ex wife actually had her sights set elsewhere. No, we're not talking about her time with Ray J (we all know how that story ended). We're talking about Kim's former fling with Nick Cannon. Remember that?

Kim Kardashian, Nick CannonKim Kardashian, Nick Cannon
John Shearer/WireImage for William Rast via Getty Images

Back in 2006, while Kardashian was still under Paris Hilton's payroll, she crossed paths with the Wild 'N Out star. The two went on to date for a few months before ultimately calling it quits in 2007. The best part? Cannon credits himself for introducing his former girl to Mr. West. The irony...

Chelsea Peretti & Jordan Peele

What do a famous comedian and horror movie mastermind have in common? Apparently, a whole lot. After crossing paths on Twitter years ago, the Brooklyn Nine-Nine actress and Get Out director went on to make things official. And it's only been uphill ever since.

Chelsea Peretti, Jordan PeeleChelsea Peretti, Jordan Peele
Kevin Mazur/WireImage via Getty Images

But the truth is we wouldn't know any better. After eloping "a bit ago," as Peretti revealed, the two have gone above and beyond to keep things under wraps. And while we might never know what's going down behind closed doors, we're sure there's a whole lot of laughs involved.

Gwen Stefani & Blake Shelton

Nope, a Nashville country star and an edgy rocker don't quite add up on paper. But after crossing paths on The Voice stage, it was only a matter of time before the Austin singer and No Doubt star proved doubters wrong. Hey, opposites attract, remember?

Gwen, Blake Shelton, CoupleGwen, Blake Shelton, Couple
Steve Granitz/WireImage via Getty Images

"I never expected that this would be where I'm at," Stefani confessed after Shelton popped the question back in 2020. Sure enough, the two have plans to tie the knot during the summer of 2021. And we'd say the star-studded wedding is lining up to be a night to remember. Keep an eye out for these two.

Harry Styles & Olivia Wilde

Harry Styles is officially on a high, and not because of all that watermelon sugar. That's right, it appears the former One Direction star is officially a man in love. And you can bet his sudden relationship with Olivia Wilde has left us with a whole lot of questions.

Harry Styles, Olivia WildeHarry Styles, Olivia Wilde
Instagram via @alicomedy

How'd they come to be? Apparently, the two first linked up on set of Wilde's latest film, which Styles is set to star in. Since then, the alleged couple has been keeping their fling on the low - but their PDA-filled outings certainly suggest otherwise. We guess we'll have to wait and see how this one plays out…

Kourtney Kardashian & Travis Barker 

Forget Kimye or Skourtney: Kourtney Kardashian and Travis Barker might just be the most confusing couple to hit the Kardashian klan. Ever since making things official in 2021, the Blink-182 drummer and reality star have left us with lots of questions.

Kourtney Kardashian, Travis BarkerKourtney Kardashian, Travis Barker
Photographer Group/MEGA/GC Images via Getty Images

The long-time friends have been living in the same gated neighborhood for years now. But their friendship took a sudden turn after making things Instagram official back in February. Since then, they haven't exactly been shy sharing their PDA on our feeds. And we'd love to know how Kris feels about this one...

Eric Stonestreet & Bethenny Frankel

Our next celebrity couple is living proof that literally, all odds are off when it comes to Hollywood. We introduce to you perhaps the most unexpected duo on our countdown: Modern Family's Eric Stonestreet and RHONY's Bethenny Frankel. Yep. We'll give you a second to take this one in.

Bethenny Frankel, Eric StonestreetBethenny Frankel, Eric Stonestreet
Kevin Mazur/Getty Images for CAA

Back in 2017, the reality star sat down with Andy Cohen to give us an inside look at her love life. And let's just say, we got a whole lot more than we bargained for. Not only did Frankel admit she and the actor once dated (well, attempted to), but they even locked lips. "She's a wonderful kisser," Stonestreet added.

Sarah Paulson & Holland Taylor

Believe it or not, the 32-year age gap isn't even the craziest part about Paulson and Taylor's love story. After crossing paths at a party back in '05, it took them a decade before the two finally made things official. And they've actually got Twitter to thank for that.

Sarah Paulson, Holland TaylorSarah Paulson, Holland Taylor
Bruce Glikas/FilmMagic via Getty Images

What happened? To put it simply: A then 72-year-old Holland slid into Sarah's DMs. Yep, you read that right. And, well, the rest is history. "I didn't choose to fall in love with the person I fell in love with," Paulson gushed. It goes down in the DMs, after all.

Machine Gun Kelly & Megan Fox

Safe to say, MGK knows how to turn heads. But forget his slew of diss-tracks for a second: We're here to talk about the artist's current relationship with a newly single Megan Fox. Not ringing a bell? One scroll on the 'gram should help fill in the blanks.

Megan Fox, MGK, DatingMegan Fox, MGK, Dating
Emma McIntyre /AMA2020/Getty Images for dcp

From loved-up selfies to romantic getaways, the two certainly haven't been shy loading on the PDA ever since making things back in June of 2020. "I knew right away that he was what I call a twin flame," Fox confessed on the Give them Lala … With Randall podcast of her 30-year-old beau. How sweet...

Lisa Bonet & Jason Momoa

For most of us, our childhood crush was exactly that - a childhood crush, nothing more. But for Jason Momoa? The Game of Thrones legend ended up marrying his - despite the shocking age gap and endless skeptics the relationship called for. (Psst, it wasn't Daenerys Stormborn.)

Jason Momoa, Lisa BonetJason Momoa, Lisa Bonet
Kevin Mazur via Getty Images

"Ever since I was 8 years old and I saw her on TV, I was like 'Mommy, I want that one,'" the GOT actor confessed of actress Lisa Bonet. Lucky for him, after crossing paths with the star in '05, he got his wish: The two went on to tie the knot in 2017, and Momoa's been living out his dream ever since.

Lil Wayne & Solange Knowles

Remember when we watched Solange hash things out with Jay in the Met Gala elevator? We've got something even crazier than her infamous feud with Mr. Carter: Her alleged secret fling with Weezy. That's right: Bey's sister and the Young Money rapper were apparently once an item. Then again, we guess that depends on who you ask.

Lil Wayne, Solange KnowlesLil Wayne, Solange Knowles
Ethan Miller via Getty Images/Frederick M. Brown via Getty Images

Despite Solange shutting down the rumors back in '07, Bow Wow claims otherwise. Back in December 2020, the rapper let it slip during a Clubhouse appearance that the two were once linked up. In fact, the way he put it? Their former fling was actually common knowledge. If that's the case, consider us out of the loop...

Amber Rose & Val Chmerkovskiy

Sure, her time on Dancing With the Stars didn't quite go as planned. But despite getting axed after six weeks, we'd say Amber Rose still managed to strike gold. Of course, we're talking about the time the reality star found love with her dancing partner's brother.

Val Chmerkovskiy, Amber Rose Val Chmerkovskiy, Amber Rose
James Devaney/GC Images via Getty Images

What happened? Back in 2016, Rose was introduced to Maksim Chmerkovskiy's brother, Val. As the story goes, the two went on to date for almost five months before calling it quits. And while her time with Wiz and 'Ye might hijack more headlines, we sure won't be forgetting this unexpected fling anytime soon.

Jada Pinkett-Smith & August Alsina

It's almost weird to think of a time when Jada and Will weren't by each other's side. But back in 2020, the internet was left buzzing after August Alsina dropped a bombshell on the Fresh Prince's marriage. As he put it, Will and his wife's relationship was not exactly as it seemed to be.

August, Jada Pinkett, AffairAugust, Jada Pinkett, Affair
Paras Griffin via Getty Images for BET

"I truly and really, really deeply loved," the rapper revealed of his infamous "entanglement" with Jada Pinket-Smith during 2015. But perhaps the most shocking part? No, not their 21-year age gap: "[Will] gave me his blessing," Alsina assured of the brief fling, which went down while the Smiths had been on a secret break.

Rihanna & Travis Scott

Remember when RiRi and Travis dated? Neither did we. But perhaps there's good reason for that. In fact, according to Complex, the artists' former relationship was intended to be kept under wraps. Why? "It's obviously embarrassing," Scott allegedly told writer Lawrence Schlossman. But wait, it's not what you think.

Travis Scott, Rihanna, DatedTravis Scott, Rihanna, Dated
Jean Catuffe/Getty Images

"It's because Rihanna's like, 'Don't tell anyone that I'm [with] Travis Scott, please,'" Schlossman explained. As he put it, the two dated in 2015, with RiRi notably in attendance at several of his gigs. Whatever the case may have been, that's one couple we'd love to catch in the studio together.

Shailene Woodley & Aaron Rodgers

Let's be real: Aaron Rodgers and Shailene Woodley's relationship seemingly appeared out of nowhere. In fact, the Divergent star herself is even surprised by the entire ordeal. "I never thought I'd be engaged to somebody who threw balls for a living," the actress joked of her NFL star fiancé.

Shailene Woodley, Aaron RodgersShailene Woodley, Aaron Rodgers
Anthony DelMundo via Getty Images/Grant Halverson via Getty Images

Sure enough, after crossing paths during 2020 - what Shailene refers to as a "wacky, whacky time" - that's exactly what happened. The two struck up a relationship almost instantly, before Rodgers got down on one knee to pop the big question. While they might clash on paper, the duo is officially a force to watch out for.

Zac Efron & Vanessa Valladares

Imagine working at a small-town restaurant when a movie star plops down at one of your tables... and asks for your number. Nope, we're not talking about a cheesy rom-com. We're talking about the all-too-real story of how Zac Efron came to meet his current beau.

Zac Efron, Vanessa, DatingZac Efron, Vanessa, Dating
Rich Polk via Getty Images for IMDb/ Instagram via @_is_ness

As the story goes, the two first crossed paths back in 2020 when the aspiring model was serving tables at Byron Bay General Store & Cafe in Australia. Since then, the 25-year-old has allegedly quit her job after making things official with Efron. From skiing outings to beachside dinners, the two seem to be living their best life.

Ciara & Bow Wow

Don't remember Bow Wow having his sights set on Ciara? Neither did he. In fact, "I didn't know I cared for her until I tried to play her," the rapper confessed of their former fling. Nonetheless, after 2 years of dating, 1 failed engagement, and endless shade, their relationship still haunts us to this day.

Ciara, Bow Wow, CoupleCiara, Bow Wow, Couple
Frank Mullen/WireImage via Getty Images

It all started back in '04 as the talented duo made their couple's debut. But fast forward to '06, and things took a sudden turn for the worst. "I let things in the past that I know was wrong affect my engagement," Bow Wow explained of their messy split.

Marilyn Manson & Evan Rachel Wood

Our next celebrity couple might be no longer, but their names have been linked together in recent headlines. After the singer and actress made things official back in '07, things didn't exactly end well. Just three years later, the unexpected duo called off their engagement. But a decade later, their split took a shocking turn.

Marilyn Manson, Evan, RelationshipMarilyn Manson, Evan, Relationship
John Shearer/WireImage via Getty Images

In 2021, 33-year-old Wood opened the lid on her former fling with the 52-year-old rocker. As she put it, Manson had severely mistreated her, in addition to several of his other former girlfriends. Whatever the case may have been, their relationship will certainly haunt us forever.

Travis Barker & Paris Hilton

Long before Travis and Kourtney were busy hijacking headlines, the Blink-182 star was busy making waves elsewhere. Of course, we're talking about his former relationship with Paris Hilton, which, safe to say, nobody saw coming. But perhaps even more shocking than the rocker and reality star linking up back in '06?

Paris Hilton, Travis BarkerParis Hilton, Travis Barker
Chris Weeks/WireImage for Pure Managment Group via Getty Images

His once-crush on Paris Hilton's former assistant: Kim Kardashian. That's right, as if things couldn't get any more... uncomfortable. "Kim was eye candy. I was [in] no way disrespectful to Paris, but I couldn't keep my eyes off Kim!" Barker confessed of his time spent with Hilton.

Michael B. Jordan & Catherine Paiz

Long before he and Lori Harvey came to bless our feeds, Michael B. Jordan was busy jetting off with another Hollywood beauty: Catherine Paiz. And while it's weird to think of the blogger not by Austin McBroom's side, her reality once looked very different.

Michael Jordan, Catherine PaizMichael Jordan, Catherine Paiz
Radcliffe/Bauer-Griffin/GC Images via Getty Images

While neither Jordan nor Paiz ever confirmed their former fling, the two were spotted looking pretty cozy together in Miami back in 2014. From jet-ski rides to strolls along the shore, their seemingly romantic getaway was certainly one for the books. Just like our next couple...

Scott Disick & Bella Thorne

It's not exactly a secret that Scott's time on our screen has been one whirlwind of a ride. But back in 2017, when the reality star stepped out with Bella Thorne, you can bet we had lots of questions. The truth? Their little fling was not what it appeared to be.

Bella Thorne, Scott DisickBella Thorne, Scott Disick
starzfly/Bauer-Griffin/GC Images via Getty Images

Well, actually, it depends on who we ask. According to Kendall Jenner, one phone call with Disick and she had all the answers she needed: "I'm doing it to make Kourtney mad," she claimed Disick had admitted to her of his sudden romance with the Disney star. Mystery solved, we guess?

Kylie Jenner & Tyga 

Believe it or not, Kylie and Tyga's story actually started a long time ago. Long before the two made things official, the then 21-year-old rapper had actually performed at Kendall Jenner's Sweet 16 - which, by the way, made Kylie only 14. (Take what you want from that.)

Kylie Jenner, Tyga, RelationshipKylie Jenner, Tyga, Relationship
Lilly Lawrence/WireImage via Getty Images

Fast forward to 2014, and the unexpected couple turned heads as they stepped out as a couple. Why? Jenner was Kim's baby sister, at only 17-years-old. Nonetheless, the two went on to date until Tyga's 26th birthday, when Kylie called it quits, as TMZ alleged.

Elon Musk & Grimes

Take one look at Musk's Twitter feed, and it's easy to see he's not your typical guy. Perhaps that's why it's no surprise the story of how the SpaceX founder came to be with his current beau is just as striking. And they've actually got Twitter to thank for that.

Grimes, Elon Musk, CoupleGrimes, Elon Musk, Couple
Taylor Hill via Getty Images

After Grimes had made a joke about artificial intelligence, an impressed Musk slid into her DM's, and, well, the rest is history. Fast forward to today, and the 33-year-old and 49-year-old might just be the quirkiest couple to grace the red carpet. And we can't wait to see where the future takes them…