Random, Surprising Celebrity Relationships

29+ Celeb Couples We Almost Forgot About


| LAST UPDATE 11/03/2021

By Chloe Becker

Whether it was a significant age gap or coming from totally different social circles, some couples in Hollywood history have surprised us with their romance. Here's a look at the most unexpected celebrity hook-ups.

Serena Williams & Drake

Before Serena Williams married Reddit founder Alexis Ohanian, she and Drake had a little something going on. It all began when cameras caught the rapper cheering on the famous athlete at an important match.

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Chris Trotman via Getty Images

And then Drake tweeted something we will never forget: "@serenawilliams I cannot wait to put it on you and make you sweat..........during our match this weekend," he wrote. We might or might not be blushing vicariously for Serena. Then the pair were seen getting cozy - and we mean cozy - on a couple of date nights.

Matthew McConaughey & Janet Jackson

The early 2000s were a magical time - an era that included rumors of this Grammy-winning singer and Oscar-recognized actor dating. And while the stars were both hesitant to confirm their romance, our beloved Andy Cohen once put McConaughey on the spot and got the answer we'd been waiting for.

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Frank Micelotta/ImageDirect via Getty Images

"There was a rumor that you once went out with Janet Jackson. Can you confirm or deny, and how would you describe your relationship with her?" Andy asked during a game of Plead the Fifth. Matthew laughed before replying, "We went and had dinner one night. That was sorta it."

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Pete Davidson & Kate Beckinsale

Even Kate Beckinsale was surprised by her relationship with Pete Davidson, who is 20 years her junior. "I've never been in this position before. Never dated anybody who comes with their own bag of mischief," she said at the time. "It's all quite shocking and something to get used to."

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JD Images via Shutterstock

While they might've since called it quits, Pete had nothing but kind words for his former squeeze. In an interview with Charlamagne Tha God, the comedian called Kate "legendary" and "hysterical." "Like one of the funniest people I've ever met. Yeah, she's really cool," he added. Wow, we wish our exes spoke about us like that!

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Katie Holmes & Jamie Foxx

Following her divorce from Tom Cruise, Katie Holmes found someone to lean on in comedic icon Jamie Foxx. Surprised to hear the Dad Stop Embarrassing Me! actor and the Batman Begins starlet dated? Wait until we reveal exactly how long their fling lasted.

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Kevin Mazur/MG19 via Getty Images for The Met Museum/Vogue

Katie and Jamie teased us for a whopping six years with their rumored romance. The power duo practically confirmed their unexpected relationship when they attended 2019's Met Gala together, only to go their separate ways a few months later. At least we'll always have this stunning photo.

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Brenda Song & Macaulay Culkin

Some fans were shocked, to say the least, after the world learned that Brenda Song and Macaulay Culkin had their first child together. "We're overjoyed," the couple said of their baby boy, Dakota Song Culkin, after the birth. So why exactly did Dakota's existence surprise many?

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Kevin Mazur via Getty Images for Stand Up To Cancer

Well, for starters, Brenda kept her pregnancy very under the radar. And the new parents have, in general, been quite hush-hush about their relationship. But while they are people of few words, when either of the lovebirds does speak, it's nearly always sweet. "You can't be around him and not be happy," Song said of Culkin.

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Tom Cruise & Cher

Cher might be sixteen years older than Tom Cruise, but that didn't stop these Hollywood icons from coupling up for some time in the 80s. That's right - the now 74-year-old singer once dated the Mission Impossible actor. "I was so crazy about him. He was so wonderful," she said.

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Trippett/Sipa via Shutterstock

When asked if she remains friends with her former boo, the world-renowned performer answered with an enthusiastic "Yeah!" But, Cher revealed there's one part of Tom's life that's somewhat confusing. "Though I don't get what he does, that whole Scientology thing. I can't understand it, so I just... don't."

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Chelsea Handler & 50 Cent

These two might've been an odd match, but they also might be one of our favorite Hollywood couples of all time. The Chelsea Lately host and the award-winning rapper? Yes, please. According to Handler, 50 Cent understood her humor and "[found] it attractive." But that's not all...

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Twitter via @chelseahandler

"I may have to get back together with 50 Cent at this point," Chelsea recently said. "We spoke the other night, and I jokingly said, 'I'm ready to get back together or possibly go for another spin...' and he was like, 'Hey, were you serious about us getting back together?' And I was like, 'Yeah, totally! I'm open to anything!'"

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Madonna & Michael Jackson

Remember that time Madonna took to Instagram to share a photo of her and Michael Jackson, along with the caption, "Best Date Ever?" Well, we'll never forget. Next on our list of unexpected couples are these two legends who attended the 1991 Academy Awards together.

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Ron Galella Collection via Getty Images

"Michael was like, 'Well, who are you gonna go with?' I looked at him and said, 'I don't know. You wanna go?'" Madonna revealed of how the date night happened. "And he said, 'Yeah, that'd be great.' And then, yes, he took me home. You wanna know what happened after that? I'm not gonna tell you."

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Kim Kardashian & Nick Cannon

Yep, it's true. A while before becoming a reality TV icon and beauty entrepreneur, Kim dated Nick. "Things could have been different, but the fact that she didn't necessarily keep it on an honest level with me kind of rubbed me the wrong way," Cannon said about their split.

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John Shearer/WireImage for William Rast via Getty Images

But get this - before Kimye filed for divorce, West once got mad at Cannon for talking about his girl. "First of all, I want to address Nick Cannon," The Life of Pablo rapper said on Instagram. "I understand that you used to date my wife, but you know, you get into an interview, don't mention my wife."

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Chelsea Peretti & Jordan Peele

While some of the random couples on this list may be long over, Chelsea Peretti and Jordan Peele have now been married for a few years. It might seem like the comedic icon, and the Us creator would have two very different mindsets on the surface. But these two were a match made in Hollywood heaven.

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Kevin Mazur/WireImage via Getty Images

The lovebugs met in 2013 thanks to social media. "Me and Jordan... met on the internet, on Twitter," Chelsea revealed. "He was very complimentary of the Web series I once did." Oh, we see you shooting your shot, Mr. Peele. Fast forward two years, and the pair got engaged.

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Gwen Stefani & Blake Shelton

How did this rockstar end up engaged (and soon-to-be-married) to this Oklahoma-native with plenty of hit songs on the Billboard Hot Country Songs chart? It's a tale as old as time: the duo met on set for a hit television show, of course. Gwen Stefani and Blake Shelton hit it off after working as judges on The Voice.

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Steve Granitz/WireImage via Getty Images

Even before they each filed for divorce from their former partners, Gwen and Blake were getting snugly during filming. But in 2016, the item went red carpet official. Since then, we've witnessed some gorgeous musical duets, lots of Instagram content, and one beautiful ring.

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Harry Styles & Olivia Wilde

These two stars might keep their relationship on the DL, but the paparazzi got the shots to prove that they might just be head-over-heels for one another (hello, being each other's plus one to a wedding). Harry and Olivia met while filming Don't Worry Darling.

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Instagram via @alicomedy

Their romance might be on the hush-hush, but Wilde complimented Styles's acting skills. "He infused every scene with a nuanced sense of humanity. He didn't have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards," she said.

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Kourtney Kardashian & Travis Barker

Kourtney Kardashian and Travis Barker make this list of random celebrity couples, but TBH, they could also land on a list of steamiest couples. One glance at either of their Instagram pages, and it's clear: these lovebirds can't seem to keep their hands off of each other.

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Photographer Group/MEGA/GC Images via Getty Images

But before things got all hot and romantic, Kourt and Travis were friendly neighbors in Calabasas. The famous musician even appeared on KUWTK along with his ex-wife Shanna Moakler. So who's to say he won't be on our screens for the upcoming final season? Fingers crossed!

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Bethenny Frankel & Eric Stonestreet

We know it might be hard to imagine Modern Family's Cameron Tucker with anyone other than our favorite red-headed man Mitchell Pritchett. But the truth is, behind the scenes, Eric Stonestreet's love interests have been quite different from his on-screen character.

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Kevin Mazur via Getty Images for CAA

And so we introduce you to the next odd match on this list: Eric and the Real Housewives of New York alum Bethenny Frankel. Believe it or not, these two were at one point an item. "She's a wonderful kisser," Stonestreet said of the reality television queen.

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Sarah Paulson & Holland Taylor

These talented ladies have been dating for over five years now, and they're going strong. It all began when Holland Taylor sent Sarah Paulson a message on Twitter. And while some might find their 3-decades age difference surprising, these lovebirds see the benefits of it to their relationship.

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Bruce Glikas/FilmMagic via Getty Images

"I think there's a greater appreciation of time and what you have together and what's important, and it can make the little things seem very small," Sarah said. "I can't say it any other way than there's a poignancy to it and a heightened sense of time and the value of time."

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Megan Fox & Machine Gun Kelly

Next up is this tatted-up stud and the iconic Jennifer's Body actress. Machine Gun Kelly and Megan Fox haven't been ones to hide their relationship ever since going Insta-official in the summer of 2020. And according to Fox, she knew MGK was the one from the moment he got cast in Midnight in the Switchgrass.

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Emma McIntyre /AMA2020 via Getty Images for dcp

"I was like, 'Who is going to play this role?' And he was like, 'Oh, we just got Machine Gun Kelly,' and immediately, I was like, 'Uh oh,'" Fox said. "Because I knew - I could feel that some wild shit was going to happen to me from that meeting, but I wasn't yet sure what. I just felt it like, deep in my soul."

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Lisa Bonet & Jason Momoa

It could be said this unlikely duo was a long time coming since, as Aquaman himself said, he's been interested in Lisa from quite a young age. "Ever since I was, like, 8 years old and I saw her on the TV, and I was like, 'Mommy, I want that one.' I'm like, 'I'm gonna stalk you for the rest of my life, and I'm gonna get you.'"

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Kevin Mazur via Getty Images

"I didn't tell her that until we had two babies; otherwise, I'd be creepy and weird," Jason continued. "I've always wanted to meet her. She was a queen, always." Lisa might be 12 years older than him, but after meeting in the mid-2000s, the celebs hit it off. Since then, they've married and started a family.

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Lil Wayne & Solange Knowles

Rewind to 2007, and the rumor mill was churning out this scandalous news: Lil Wayne and Solange Knowles were dating. When things escalated, and some media outlets claimed Bey's sister ditched her first husband for the famous rapper, Solange finally spoke up and denied the claims.

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Ethan Miller via Getty Images/Frederick M. Brown via Getty Images

"That's absolutely not true," she said. "Yes, we know each other, but I absolutely did not leave my husband for him." Then again, Solange didn't say there wasn't something between her and Wayne. Skip a couple of years to 2020, and Bow Wow blessed us by confirming the romance.

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Amber Rose & Val Chmerkovskiy

These random lovebirds met through Val's sibling, who was Amber's co-dancer on Dancing With the Stars. After a few months, the couple broke up and made headlines when Rose was photographed kissing ex Wiz Khalifa not long after. So the model took to Instagram to clear the post-breakup air.

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James Devaney/GC Images via Getty Images

"To the Awesome person I got to spend the past 5 months with (Val) and I broke up due to our own personal reasons but we still care about each other tremendously and we love each other's families even more," Rose said. "Nobody got dumped and nothing we do over here is malicious its just how life works sometimes."

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Jada Pinkett Smith & August Alsina

Some of us were left speechless when August Alsina admitted he'd secretly dated Jada Pinkett Smith. "I totally gave myself to that relationship for years of my life," he said of the romance. "I devoted myself to it; I gave my full self to it... I can die right now and be okay with knowing that I truly gave myself to somebody."

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Paras Griffin via Getty Images for BET

When rumors started affecting Alsina's business ventures, he came clean about what really went down and revealed Jada and Wil were taking a hiatus from their marriage at the time. The famous couple - we're referring to the Smiths now - later confirmed they'd gone through a rough patch, and August was not a home-wrecker.

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Rihanna & Travis Scott

When Complex magazine spilled the beans on Rihanna and Travis Scott after interviewing the rapper, chaos ensued. The Astroworld artist reportedly got upset with the publication for revealing their romance since, as the interviewer put it, Rihanna was "embarrassed."

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Jean Catuffe via Getty Images

We're not sure why Riri wasn't proud, but we stan this couple. Well, maybe not now that Travis shares a child with Kylie Jenner. But we sure loved seeing the Anti singer attend Scott's gigs back in the day. Not to mention it made our stomachs flutter when he called the singer "creative" and "inspiring" - we couldn't agree more, Travis!

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Shailene Woodley & Aaron Rodgers

This Green Bay Packers quarterback scored his dream girl. Except it's not the head cheerleader - it's Big Little Lies star Shailene Woodley, duh. Fans on both sides were surprised when the 37-year-old athlete and the 29-year-old actress announced their engagement.

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Anthony DelMundo via Getty Images/Grant Halverson via Getty Images

After all, the news came a mere days after romance rumors hit the headlines. And it seems that Shailene is just as shocked as the rest of us at this unlikely match. "I never thought I'd be engaged to somebody who threw balls for a living," Woodley hilariously said.

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Zac Efron & Vanessa Valladares

It seemed like a real-life fairytale when the world learned of Zac and Vanessa's love story. A famous actor falling for his waitress while visiting Australia? Believe it or not, that's exactly what happened. But this tale sadly doesn't have the happiest ending.

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Rich Polk via Getty Images for IMDb/ Instagram via @_is_ness

After ten months of being photographed holding hands, allegedly living together in a gorgeous home, and falling madly in love, things took a tragic turn. Media outlets reported the lovebugs broke up due to a two-month-long filming project on Zac's agenda.

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Ciara & Bow Wow

This might seem like forever ago now, but Ciara and Bow Wow were once not only dating but engaged! Yup, the 1,2 Step starlet and the Let Me Hold You singer used to be very much an item. Too bad the award-winning actor didn't realize how good he had it until they split...

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Frank Mullen/WireImage via Getty Images

"I didn't know I cared for her until I tried to play her," Bow Wow admitted. "I let things in the past that I know was wrong affect my engagement. That's what was eating me alive." Long (and messy) story short: the artist was unfaithful to Ciara, and she said thank you, next.

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Evan Rachel Wood & Marilyn Manson

Surprised that the West World star and the hard rock performer, whose stage name was inspired by infamous cult leader Charles Manson, ever dated? Yeah, you're not alone. The pair dated from 2007 to 2010 and went their separate ways seven months after getting engaged.

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John Shearer/WireImage via Getty Images

But their relationship was back in the headlines eleven years later as Wood revealed disturbing details about her former romance with the singer, who's nearly two decades older than the actress. Evan Rachel said Marilyn "brainwashed and manipulated" her and other women.

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Paris Hilton & Travis Barker

This Hollywood hookup was, shall we say, complicated. "It was actually a sad time 'cause my wife, and I had just split up, and literally the weekend after we split up, Paris and I met each other," Travis told Complex. "And we were having the time of our life in every country, flying from country to country."

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Chris Weeks/WireImage for Pure Managment Group via Getty Images

To make matters even more interesting, the Blink-182 drummer admitted he also took a liking to Hilton's personal assistant at the time: Ms. Kardashian. "Kim was eye candy. I was [in] no way disrespectful to Paris, but I couldn't keep my eyes off Kim!" Travis said. Well, we hope Kourt is as understanding as the hotel heiress was.

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Michael B. Jordan & Catherine Paiz

Previous to coupling up with now-hubby Austin McBroom, Catherine Paiz hit the beach in Miami with Michael B. Jordan. You read that right - before the Ace family became the Ace family, the mother-of-three was having fun in the sun with the Black Panther actor.

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Radcliffe/Bauer-Griffin/GC Images via Getty Images

Although neither star has ever spoken publicly about their steamy fling, there are plenty of photos to prove it. Paparazzi and fans spotted Michael and Catherine taking romantic beach strolls and playing water sports together during their little vacay.

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Bella Thorne & Scott Disick

Remember when Scott and Bella hit the town together? As if we could ever forget. Luckily for the former Disney Channel star, the relationship didn't get her in trouble with the Kardashian empire. "I'm very friendly with Kylie and Kendall," Thorne said at the time.

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starzfly/Bauer-Griffin/GC Images via Getty Images

She added., "Kylie and I used to be very close... As far as [I] know, we're chill. I didn't have any problem with them." But that doesn't mean the Jenners kept their mouths shut on the topic. In fact, Kendall revealed that Scott told her he dated Bella "to make Kourtney mad." The tea is piping hot!

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Kylie Jenner & Tyga

Some people were pretty scandalized by this pair's age gap: Jenner was 17 when the relationship was confirmed, while Tyga was nearing 25. But according to sister Khloe, their romance was a "special case." After all, it's safe to say Kylie wasn't your average teen.

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Lilly Lawrence/WireImage via Getty Images

"You're not gonna say, 'Hey, so what are you doing this weekend?' and have her say, 'Having a slumber party at my girlfriend's,'" Khloe explained of why their fling was acceptable. "Kylie is taking business meetings... or she's going on a private plane with Karl Lagerfeld to take a meeting."

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Grimes & Elon Musk

At this point, there's hardly anything that can surprise us from this eccentric couple. After uniquely naming their first child together X AE A-XII, everything's fair game. And while the tech mogul and the singer are quite the random match, they sure know how to rock the Met Gala together.

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Taylor Hill via Getty Images

So how did these two lovebirds couple up? Well, Musk took a liking to the starlet after seeing a clever tweet she posted. And as any tech guru would do, the billionaire then sent her a DM. It seems Grimes liked what she saw because they've been dating since.

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