29+ of Hollywood's Most Random Matches
| LAST UPDATE 03/17/2022
While few might actually remember Kim Kardashian with Nick Cannon or Travis Barker with Paris Hilton, these couples are all too real. Stick with us as we look at some of Hollywood's most bizarre flings from over the years.
Drake and Serena Williams
Drake's not one to hide his feelings. And while the rapping legend has had many baes over the years, there was one romance that still confuses us. That's right, we're throwing it back to Serena and Champagne Papi's 2011 fling.
While the 2 never confirmed their fling at the time, the gossip didn't stop. Rumors first started when Drake was seen posted up in the stands at Serena's tennis match. And from there? Well, their smooches caught by the paps didn't really help… In 2013 Drizzy eventually hit the studio to rap about the fling, as he does best.
Matthew McConaughey and Janet Jackson
This was not your average Hollywood match. Perhaps that's why the charming country boy and Grammy-winning artist took us by surprise when they first kicked off their fling. Janet Jackson and Matthew McConaughey met in the early 2000s and immediately felt the vibes. But what came after?
Well, not much. "We went and had dinner one night. That was sorta it," McConaughey shared on Watch What Happens Live. It seemed like Janet agreed: She barely ever mentioned it because of how short their fling really was. Sorry, Ms. Jackson, but we'd say you let a good one get away!
Pete Davidson and Kate Beckinsale
Lucky for Pete, at least this fling doesn't end with a chart-topping pop song. Nonetheless, his romance with English actress, Kate Beckinsale wasn't any less random. OK, so no identical tats or big proposals here, but the 2 definitely turned heads during their short flame.
Looks like we were not alone with the confusion: "It's all quite shocking and something to get used to," Kate later confessed of their former relationship. Safe to say, the unexpected couple shocked many with their 20-year age difference - as well as their courtside make-out sesh.
Jamie Foxx and Katie Holmes
Next up for unlikely rebounds is Tom Cruise's ex-wife, Katie Holmes, and the talented Jamie Foxx. These two grabbed major attention at the 2019 Met Gala... and not for their outfits. The pair strutted down the red carpet together and weren't afraid to show a little love along the way.
But this was actually far from a fling: Katie Holmes and Jamie Foxx were actually together for 6 years but eventually called it quits in 2019. But while their time together may be over, our confusion certainly stays the same... But wait, there's more where that came from.
Brenda Song and Macaulay Culkin
Brenda Song and Macaulay Culkin may not look like they have much in common, despite being former child actors. But, to the surprise of many, sparks flew for the 2 back in 2017. The Changeland co-stars even wowed their director, Seth Green, who said he "didn't see that one coming," after they started dating off-set.
But the unexpected news actually doesn't end here for Brenda and Macaulay: The 2 welcomed their first child back in April, and people on the Internet were left buzzing. These new parents clearly did a great job keeping the love alive and away from the camera. Congrats, you 2!
Tom Cruise and Cher
Long before Tom Cruise made his debut with Katie Holmes, he was busy cozying up to another Hollywood starlet: Cher. Back in 1985, the two first made eyes at Sean Penn and Madonna's wedding and decided to give things a shot. But this was no average fling.
In Cher's eyes, Tom ranked as one of her "top 5 lovers." She even confessed that she "was so crazy about him." Clearly, age was just a number for the star-crossed lovers, who linked up despite their 16 year age difference. One thing's for sure, this picture is going to live forever in our minds.
50 Cent and Chelsea Handler
Well, 50 Cent and "lovey-dovey" might not technically go together. But according to Chelsea Handler, he's a "big fat teddy bear." After meeting on the set of Chelsea Lately, the P.I.M.P. rapper pulled out all the stops to get his girl. Take notes, this charmer knew what he was doing.
The In Da Club artist won Handler the old-fashioned way: Roses. "He started sending me flowers - but ridiculous amounts of like 50 white roses," Chelsea revealed. Clearly, it got the job done because the fling lasted a good few months before the 2 went their separate ways.
Madonna and Michael Jackson
Ok, so these pop stars might not have made for the most surprising match. But they caused a whole lot of drama on their famous date back in 1991. Back when the 2 walked the Oscars red carpet together, it wasn't Madonna's insane beauty that was busy turning heads.
What happened? Madonna sure kept us guessing: "You wanna know what happened after that? I'm not gonna tell you," she teased. But after years passed, the Material Girl singer finally spilled the tea: They smooched. And now at 62-year-old, she can confirm that it was the "best date ever."
Kim Kardashian and Nick Cannon
Way back before Kim's 72-day marriage to NBA baller Chris Humphries, we were introduced to another unlikely pairing. We're throwing it back to the time when Kimmy dated comedian, Nick Cannon. Doesn't ring a bell? Sit tight, because this story's got an even weirder twist.
The pair met back when the young socialite was still number 2 to her bestie, Paris Hilton. She and Cannon had a good run for a few months before the spark died out. But the twist? Nick claimed that he set Kimye in motion, introducing the pair way back when. Well, look how that played out...
Chelsea Peretti and Jordan Peele
Former Brooklyn Nine-Nine funny girl and the Get Out creator have found love in the oddest of places. The unlikely couple met down in Twitter's DMs, of course, and years later went public with their relationship. Hey, when you know, you know, right?
Unlike most of our shocking Hollywood couples, these 2 are still going strong today. They eloped privately and have since welcomed their first son, named Beaumont Gino Peale. Though the pair clearly like to keep their romance on the D-L, we can only assume that their house must be one long stand-up special.
Gwen Stefani and Blake Shelton
They say opposites attract, right? While their careers took them on very different paths, these star-crossed lovers met while working on The Voice… And the rest is history. The former No Doubt front girl and the country star may be fighting over the aux cord, but their different tastes are clearly not a deal-breaker.
"I never expected that this would be where I'm at," Gwen gushed following Blake's proposal in 2020. With arrangements to marry this summer, it's clearly just the beginning for these lovebirds. We're guessing the 2 will tie the knot with A-list guests. Stay posted for the nuptials, this is not a wedding most will want to miss.
Harry Styles and Olivia Wilde
One of the more recent additions to our list has left as pretttty confused. After her recent split from comedian Jason Sudeikis, Olivia Wilde sparked major buzz after scoring what many would agree to the world's best pick for a rebound: former One Direction singer, Harry Styles.
If you're like us, you may be needing a little background info behind this unlikely pairing. The 2 reportedly first met on the job, after Harry was cast in Wilde's latest film. And while we're waiting on a confirmation from the pair, they're certainly not hiding their love from the paparazzi!
Kourtney Kardashian and Travis Barker
Looks like Kourtney has done a great job getting over her exes. Nonetheless, her new man is... an unexpected choice for the 42-year-old mom of 3. But ever since Kourt and Travis Barker went public earlier in the year, they've been bringing us non-stop PDA. And we're scrambling for answers.
But these 2 lovebirds actually go way back. They've been pals for years and even own houses in the same exclusive neighborhood. So what changed? The deets of their steamy fling - that started in February - are still unclear, but according to their NSFW Instagram posts, the spark is real.
Eric Stonestreet and Bethenny Frankel
These 2 TV stars came from opposite sides of the entertainment industry, making them one of our most unlikely couples. Turns out you can't judge a book by its cover, but man are these books different. That's right: We're talking about reality star Bethenny Frankel and Modern Family's Eric Stonestreet.
In a sit-down with Andy Cohen, the RHONY cast member spilled the tea on the bizarre match. In 2017 she confirmed that the 2 once dated, well attempted to. And thanks to Stonestreet's confirmation, we know the pair even smooched: "She's a wonderful kisser," he admitted.
Sarah Paulson and Holland Taylor
Most would agree that social media can sometimes get ugly, but it also has it perks. We think actresses Sarah Paulson and Holland Taylor would agree, since they owe their relationship all to Twitter. Despite meeting back in 2005, it took them another 10 years before getting together, all thanks to a little DM action.
You read that right, looks like celebrities also shoot their shot in the DMs. Back in 2015, Taylor messaged Paulson, and the rest is history. Safe to say, the 32-year age gap isn't pumping the breaks for the lovebirds. "I didn't choose to fall in love with the person I fell in love with," Sarah explained.
Machine Gun Kelly and Megan Fox
We've got a pretty good feeling you've already heard of our next unexpected match made in Hollywood. Of course, we're talking about one of LA's most eligible bachelorettes finding love with the relentless king of diss-tracks, Machine Gun Kelly. And for her sake, we hope things go well...
The 2 became official in the summer of 2020, and since then, it's been nothing short of entertaining. But while their PDA-filled posts might still take getting used to, Megan feels otherwise: "I knew right away that he was what I call a twin flame," she said on an episode of the Give them Lala... With Randall.
Lisa Bonet and Jason Momoa
While some celebrity crushes fade over time, some lucky few turn their fantasies into reality.That's right, we're talking about Jason Momoa. The Aquaman star finally got his girl, Lisa Bonet, after endless years - making him a step-dad to Zoë Kravitz with only a 9 year age gap!
But his and Lisa's 12 year age gap hasn't scared them away one bit. In fact, Jason's had his eyes on the prize (AKA Lisa) since the age of 8! Eventually, they finally met in 2005. And after saying, "I do" back in 2017, they have welcomed 2 kids of their own.
Lil Wayne and Solange Knowles
We thought Solange's juiciest headline would be the notorious elevator incident with Jay-Z at the 2014 Met Gala. But this secret fling came in at close second. Turns out back in the day, Knowles and Lil Wayne had a fling so under wraps that the Stay Flo singer never even acknowledged it.
Solange squashed the rumors back in the day. But fellow artist Bow Wow had a different side of the story. In 2020, the rapper finally confirmed that the two were once an item. According to him, the romance was actually well-known. Well, guess we've just been under a rock then...
Amber Rose and Val Chmerkovskiy
Just when we thought Amber Rose's stint on Dancing on the Stars was memorable enough, she managed to shock us even more with the romance that soon followed. Though Rose only lasted 6 weeks in the competition, we'd say she took home the best prize: Her dance partner's brother.
In 2016, Amber and Val were introduced by famed dancer, Maksim Chmerkovskiy. The unlikely duo carried out their romance for nearly half a year before they went their separate ways. Now, Val's no Wiz Khalifa or Kanye, but Amber's former ex is certainly stuck in our heads.
Jada Pinkett-Smith and Augusta Alsina
The Fresh Prince and his Mrs. were always seen as ride-or-die until news broke of a certain entanglement: Jada Pinket-Smith and Augusta Alsina's secret fling from 2015. While the Smiths would have preferred to keep things private, Jada's ex-flame set the Internet on fire with his side of the story.
August admitted that he "truly and really, really deeply loved" during his past fling with Jada. And while most of us were wilding out over the 21-year difference in age, Alsina's later confession sent us over the edge: "[Will] gave me his blessing," the artist revealed, regarding his 2015 flame.
Rihanna and Travis Scott
Yes, you read that right: the 2 artists dated back in 2015. But don't worry, you weren't living under a rock, the pair purposely kept things hush-hush during their brief fling according to Complex. As journalist Lawrence Schlossman saw it, Kylie's Baby Daddy apparently confessed that "[it was] obviously embarrassing." Say what?
According to him, Rihanna wanted the romance kept under wraps. Despite being seen at a number of the rapper's concerts, "Rihanna [was] like, 'Don't tell anyone that I'm [with] Travis Scott, please,'" the writer claimed. We may never know what went down, but we'd sure love to get these 2 on a track together.
Shailene Woodley and Aaron Rodgers
Safe to say, not many saw this one coming. But leave it to the Big Little Lies star and NFL quarterback to find love in the unlikeliest of places. We were even more shocked to find out about their engagement - and Shailene agreed, joking about the sudden romance during a recent interview on The Tonight Show.
"I never thought I'd be engaged to somebody who threw balls for a living," the Divergent star joked about her fiancé, Aaron Rodgers. But hey, love is blind, right? The pair have had a whirlwind romance ever since meeting back in 2020. And it didn't take long before the Green Bay Packers QB put a ring on it.
Zac Efron and Vanessa Valladares
Who would have thought a regular waitressing shift at a café could land you a date with one of Hollywood's most eligible bachelors? Well, turns out this cheesy movie plot became a reality for Australia-born model Vanessa Valladares and her celebrity ex-boyfriend.
After meeting while she was on the job at a Byron Bay Café, Efron made his move and got his girl. While brief, the fling brought Valladares a great deal of attention. And with exciting dates at the beach and alpine getaways, we weren't surprised to learn the aspiring model left her job when she shacked up with Zac.
Ciara and Bow Wow
You never know what you've got 'til it's gone, right? Looks like Bow Wow learned his lesson the hard way with his former flame, Ciara. The unlikely pair definitely hit some bumps over their 2-year relationship. With a called-off engagement and tons of beef between them, safe to say this one's best left in the past... Or is it?
Let's start at the beginning: We saw the sparks in 2004 when the lovebirds made their public debut, but 2 short years later, it was a totally different story. "I let things in the past that I know was wrong affect my engagement," the rapper confessed after the breakup. Yikes!
Marilyn Manson and Evan Rachel Wood
Ok, while this fling is long in the past, recent press has brought this duo back into the spotlight. Marilyn Manson and Evan Rachel Wood officially started dating in 2007, but it didn't take long for things to go south. After 3 years together, the rocker and actress went their separate ways, breaking off their engagement.
10 years later, Evan grabbed the mic to share her side of the story. According to her, Manson had a nasty habit of treating his girlfriends in a less than gentlemanly manner. Better off without him, Evan. But regardless of the reason behind their breakup, safe to say this random match will forever spook us.
Travis Barker and Paris Hilton
Congratulations Travis, your taste in women has landed you on our list twice. This time, it's thanks to his 2006 fling with Hollywood's it-girl, Paris Hilton. We think most would agree, this duo came out of nowhere. But that's not even the most surprising part about their entire affair.
According to Travis, back when he was with Hollywood's favorite tabloid target, his heart actually wanted Kimmy. "Kim was eye candy. I was [in] no way disrespectful to Paris, but I couldn't keep my eyes off Kim," he confessed. Watch out, Kourtney, you might just have competition!
Michael B. Jordan and Catherine Paiz
Way back before Michael B. Jordan and Steve Harvey's daughter took to Instagram to share their love, he was keeping busy with another LA hottie: Catherine Paiz. Today, it's clear that she and her hubby Austin McBroom are a match made in heaven, but back in 2014? It was a different story.
While MJB and Paiz never confirmed their fling, it looked pretty hot and heavy for a second. Or are we just heading off on romantic Miami getaways with all of our close friends now? Whatever the truth really was, this pair definitely made heads turn. But wait, there's more...
Scott Disick and Bella Thorne
The deets of Lord Disick's romantic life have been put on blast since he joined the KUWTK empire. And while we followed along throughout the Kourtney and Sofia Richie roller coaster, this former fling made absolutely no sense to us. And clearly, we were right...
Well, it depends whose side you hear. The eldest Jenner daughter has her own take on the story. According to Kendall, Scott fessed up during a phone call, claiming he was "doing it to make Kourtney mad." A little extreme, don't ya think, Scott? But hey, at least that answers our question about how this bizarre match came to be.
Kylie Jenner and Tyga
This couple goes back further than we'd care for. Long before the model and rapper made their relationship public, Tyga actually made an appearance at Kendall's 16th birthday. That's right: These two go all the way back to when Kylie was just 14-years-old and the artist was 21.
Back in 2014, the couple made major news when they were spotted together for the first time. The youngest of the Jenner gang wasn't even 18-years-old at the time, but that didn't stop these two. According to TMZ, the pair stayed together until Tyga's 26th birthday, when they decided to go separate ways.
Elon Musk and Grimes
SNL's controversial host has never been one to keep his opinions to himself. And while most of his tweets cause major scandal, the Tesla mastermind has Twitter to thank for introducing him to his latest partner: singer Grimes. Let's just say, these 2 have more in common than we thought.
It all started with Grimes's tweet poking fun at AI. Musk saw his chance to shoot his shot and went for it. After a little DM action, the 2 made it official and have been raising eyebrows ever since. Despite the 16 year age difference, things are clearly going well for the pair, and they have since welcomed their first child.
Pete Davidson & Kim Kardashian
It wasn't long after these two were sharing the screen on Saturday Night Live that many started to gossip about the possibility of them dating. Fans didn't believe that Kim Kardashian was possibly in a relationship with the comedian, Pete Davidson. That was until they were spotted getting dinner together.
The rumors proved to be true! Despite being from different worlds, these two celebs made things official. And while they tried to remain on the low for a bit, the reality star recently shared a few Instagram pictures featuring the SNL star. We can't help but be happy for the couple!
Ben Affleck & J. Lo 2.0
While many fans adored their relationship back in 2002, they never expected them to reunite nearly 20 years later. So, when Ben Affleck and Jennifer Lopez were reported to be back together, the internet went crazy! Who knew this celeb couple would finally find their way back into each other's hearts.
According to J. Lo, we won't ever have to go through the two of them splitting up again. As she revealed, "I don't think we would have got back together if we thought that was where it was headed." Basically, she doesn't foresee a break. Does anyone else hear wedding bells...or is it just us?
Anna Kendrick & Bill Hader
In 2019, Bill Hader and Anna Kendrick both appeared in the movie Noelle. But the two actors didn't just work well together as co-stars, but also as a couple. No one in the public was aware, but these stars started secretly dating one another after connecting on set.
The relationship wasn't as shocking as the fact that they were able to keep their status on the low for nearly an entire year! And we totally get why. Hollywood relationships tend to fizzle out when the media becomes too involved. But this unexpected comedy duo has managed to make things work for them.
Kanye West & Julia Fox
Kanye West surprised his fans when he all of a sudden announced he had a new girlfriend, Julia Fox. It wasn't that he was in a relationship that was astonishing - it was the fact that he was so adamant about getting back his ex-wife, Kim Kardashian at the same time.
The couple debuted their connection by posing for a sensual photoshoot that was exclusively released on Interview Magazine. Fox shared private details about the new romance, explaining to fans that they had an "instant connection." But the infamous duo didn't last too long, as they called it quits around 2 months later.
Lance Armstrong & Ashley Olsen
In 2007, the world was shocked to learn about the latest celebrity pairing. Ashely Olsen had formed a relationship with professional cyclist Lance Armstrong. But it wasn't just that they were from opposite worlds that stood out to fans, it was the couple's ages.
At the time, the former child actress was 21 while her beau was 36! They had an age gap of 15 years, and the media weren't the only ones stunned by this. Apparently, Armstrong's friends disapproved of the age difference and pursued the athlete to end things with the Full House star.
Michelle Rodriguez & Zac Efron
Up next on the list of unexpected celeb couples, we have Michelle Rodriguez and Zac Efron. The pair were first seen spending time together in Ibiza, Spain. And it was clear they were together - after all, the paparazzi snapped many pics of them all over one another.
But the Fast and Furious star didn't last long with the former Disney actor. After two months of their alleged relationship, they were finished with each other. We're still not sure what caused the split. But we're gonna assume it was just a summer fling.
Justin Timberlake & Fergie
At 16 years old, it seemed like Justin Timberlake was starting to have it all: fame, fortune, and a new beau. He and Fergie started dating, except the former Black Eyed Peas lead singer was 23 at the time. Despite the age gap, the two stars spent a bit of time together back in the 1990s.
It was all happening while Fergie was traveling with her then-band Wild Orchid, who was touring with NSYNC. The unpredictable duo received lots of attention, especially because Timberlake was a teenager at the time of their alleged fling. 10 years later, Fergie finally explained, "It wasn't all that serious."
Lenny Kravitz & Nicole Kidman
Once upon a time, Lenny Kravitz was Nicole Kidman's landlord. Funny enough, that's how the two celebs started dating one another back in 2002. Despite both being famous, they kept their status hidden from the media. They even secretly got engaged! "I wasn't ready. We weren't ready," Kidman explained why they never married.
15 years later, Kidman worked with her ex-fiance's daughter, Zoe Kravitz. Zoe revealed to Entertainment Tonight, "I hadn't seen her in a long time before Big Little Lies, but there was a point where we were all kind of living together," she added. "I was about 13, and she would take me to see movies; she was so nice to me."
Madonna & Tupac
While they were both mega big in their respective music genre, no one ever saw this relationship coming. Madonna and Tupac surprised fans when rumors of the two datings started circulating. Although at the time, neither one ever confirmed anything, Madonna finally shared details 25 years later.
The Material Girl artist confessed, "I was dating Tupac Shakur at the time, and the thing is he got me all riled up on life in general," she said. "So when I went on the show, I was feeling very gangsta." More info of the two was revealed when a handwritten letter written by Tupac to the pop diva was leaked.
Olivia Munn & John Mulaney
It didn't take long before John Mulaney was in a new relationship after officially divorcing his wife. The news was headlining everywhere that the comedian started seeing actress Olivia Munn. Safe to say that no one saw that it coming, and the two were arguably one of the most unexpected duos of 2021.
It wasn't that Mulaney had just gotten out of a 6-year long marriage that worried fans - it was the fact that the comedian was dealing with substance abuse problems. Even though they had many haters, the two quickly revealed to the world they were expecting a baby. How sweet!
Channing Tatum & Zoe Kravitz
It didn't take long for fans to start speculating that Channing Tatum and Zoe Kravitz were a thing after they were seen together on numerous occasions. The pair claimed that they were not together, but after a while, they finally stopped keeping the relationship private.
From PDA-filled outings to showing up to the Met Gala together in September of 2021, it was clear the two were a couple. And while when they were first spotted with one another in 2021, many people were confused by the pairing, by now they have received approval from many fans.
Hunter Schafer & Dominic Fike
With nearly all teen dramas comes a real-life relationship between co-stars. It's no secret that Euphoria is arguably well known for its many love interests on the show. And as it turns out, those romantic vibes seem to present between the actors on the HBO show.
Hunter Schafer and Dominic Fike had fans stunned when they were spotted holding hands after enjoying dinner at the Nice Guy restaurant in Los Angeles. Ironically the characters the two play, Jules and Elliot, also had a few instances where they were intimate. We can't help but approve of this cute couple.
Macaulay Culkin & Mila Kunis
Back in 2002, Macauley Culkin and Mila Kunis formed a relationship with one other. But unlike many other unexpected couples, these two lasted a while. It wasn't until 9 years later that the Home Alone star and the That 70's Show actress called it quits.
When they first started dating, they were both young, with Kunis being 18 and Culkin 21. The actress admitted during an interview with Women's Health Magazine, "We grew up together," she said in 2009. "You find a steady rock in your life, and that's all you need. We have our ups and downs, but work through them."
Daryle Sabara & Meghan Trainor
This celebrity couple had the internet completely shook! It's safe to say that no one would have guessed that Meghan Trainor and Daryle Sabara would have ever dated, let alone get married and have a kid together! But, as it turns out, they instantly clicked when they first met through a mutual pal.
In 2016, Chloe Grace Mortez told Trainor that she had a friend for her whom she thought would be a good match, and she was right! The Spy Kids actor and the All About That Bass singer came from separate worlds, but they somehow find a way to each other, and honestly, they are adorable!