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...
Tyga & Avril Lavigne
He was a boy, she was a girl, and they couldn't be making their new fired-up romance any more obvious. The Sk8er Boi singer recently announced that she and her ex-fiancee, Mod Sun, had broken off their engagement. The punk rock pair got engaged in March 2022, but their on-and-off narrative had been rocked out too far.
Since then, Lavigne has been seen with rap artist Tyga. Sources told TMZ that there are no labels just yet, despite the two getting cozy at Paris Fashion Week. Despite speculation that the romance is a marketing boost for a music collab, this rumor has been shut down. Still, we never thought these rap and rock worlds would collide.
Bad Bunny & Kendall Jenner
Things are heating up for one of America's top models and the Puerto Rican rapper. It is no secret in the pop culture world that all eyes have been on them recently. The pair were first seen together in February at a fancy restaurant, but they have been in this industry far too long to know what's up. Hence, they left at separate exits.
Jenner's ex Devin Booker recently unfollowed her on Instagram, and Bunny has offered his shoulder to cry on. The duo was spotted getting close after a rumored date night last week, leaving Jenner smitten - and then again leaving the Oscars afterparty together while trying to avoid the paparazzi! We'll be keeping a close eye on them.
Madonna & Josh Popper
After Madonna went on a little social sabbatical, she returned with a post that got everyone talking. In the early days of February, Popper shared a celebratory collection of photos by the boxing ring, giving a shoutout to those who have stood by him, one of which included the pop singer herself.
Popper (23), Summer House star, met Madonna (64) while training her son. Vanity Fair hinted they are romantically linked after hanging out. And they became 'Instagram official' when the singer posted a snap of her kissing the athlete, who was wearing his own black face covering, captioned, "Killers who are partying." Nothing to hide here.
Pete Davidson & Emily Ratajkowski
This man needs no introduction. The King of Staten Island, also known as Pete Davidson and ultimate ladies' man, was previously connected to supermodel and supermom Em Rata. Davidson has been through quite the A-list roster, from Ariana Grande and Kim Kardashian, and then became involved with Rata in November 2022.
The pair were spotted on dates, romantic strolls and even attended a New York Knicks game together, where they publicly confirmed their dating era. Let's just say, when Davidson shoots, he scores. While Rata was just coming out of a divorce, the relationship didn't last very long, and Page Six reported their split a few months later.
Drew Taggart & Selena Gomez
Please, guys, don't let us down with this one. Back in February 2023, sources told ET that the Chainsmokers star and Calm Down singer were getting a lot closer. With all the hustle and bustle going on in the news amid the classic Hailey and Selena drama, we should really be focusing on the positives, like this reported couple.
The source noted, "Selena and Drew are having a lot of fun together… Drew is really happy around Selena, and Selena is into Drew too. They have connected over their love of music, being in the same industry, and their strong work ethic." After meeting through mutual friends, the couple is seemingly still fresh as a daisy. Stay tuned.
Tom Sandoval & Raquel Leviss
If you haven't been living under a rock recently, then you are fully aware of the biggest Bravo scandal, #Scandoval. SUR bartenders, and stars of Vanderpump Rules, Tom and Ariana (Madix), were dating for almost 10 years. However, they have recently split after Madix discovered her partner was cheating with a fellow SURver!
It has come to light that Tom Sandoval had been having a 7-month affair with co-star Raquel Leviss, who was also involved with Tom Schwartz, Katie Maloney's ex-husband, and previously engaged to James Kennedy. Let's just say it's a total hot mess. But the cameras are rolling, and the drama is set to unfold in the current season.
Jack Harlow & Dua Lipa
We can start with the fact that Harlow dropped a song titled Dua Lipa in 2022, but it's better to give some context to the situation. The Levitating signer has had a vast dating history, including eras with Trevor Noah and Anwar Hadid - but things got intense when the world found out about her first-class fling.
In December 2022, Cosmopolitan reported there was "a cool new couple in town." Sources claimed Dua was "quite smitten," and the pair were non-stop for some time, which led to Harlow's release. He even asked Dua for permission to release the track, with lyrics that read, "Dua Lipa, I'm tryna do more with her than do a feature."
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.
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?
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.
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.
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.
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.
"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.
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.
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?
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.
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?
"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 has been capturing the hearts of many since day one, and one of those was Olivia Wilde’s. The two were together from early 2021 to late 2022 and shocked – yet delighted – fans everywhere. People remain curious about what went on during their whirlwind romance, wondering if love truly bloomed between the two stars.
Fans were shook when PEOPLE reported the couple officially called it quits in Nov. ‘22. A source close to them shared that it was a "very amicable decision," with both stars focusing on their own life paths. As much as we wanted 'Hivia' to find happily ever after, at least we know they can still stay on good terms.
Kourtney Kardashian & Travis Barker
Forget Kimye or Skourtney - fans were shook when they heard that Kourtney Kardashian and Travis Barker had taken their longtime friendship to the next level. Since February 2021, the two have been posting pics and stories on social media that have had fans obsessing over them for months!
April 2022 marked the beginning of a journey for this celebrity couple when they got married for the first time. But saying "I do" once wasn't enough for these two! A month later, they exchanged vows once again in a romantic ceremony. But their grand finale was saved for July, when they tied the knot in Italy in style.
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.
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.
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
For quite some time now, Machine Gun Kelly and Megan Fox have been making headlines with their wild love story! From romantic poems to strange rituals, this power couple is the talk of social media. After a few years of dating, MGK and Megan have got engaged - and fans can't get enough!
From romantic gifts to daring adventures, the couple has kept us up-to-date with their relationship on social media. But fans of the pair were met with a shock when Megan deleted all photos of MGK from her Instagram! This sudden move has left fans wondering if this power couple is still together or not? We'll have to wait and see…
Lisa Bonet & Jason Momoa
Remember that childhood crush you had back in the day? Well, for Jason Momoa, that fantasy became a reality. At 8-years-old, he saw his future wife, Lisa Bonet, on TV and decided then and there she was the one. Fast-forward many years later, Momoa's dream of marrying Bonet finally came true.
After 5 years of marriage and 2 kids later, the couple announced their split in early 2022. But are they really done? During the 2022 holiday season, they were spotted spending time together—evoking the same sweet butterflies of young love all over again. And fans are waiting to see what happens next...
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.
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.
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.
"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.
"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.
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.
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.
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.
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?
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.
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.
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.)
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
The couple's journey began on the platform now owned by the tech giant himself. Before buying Twitter, he was an avid user, posting his thoughts and opinions that often sparked worldwide debate. But he also used it for something else - to reach out to his future partner! Who knows if they would have ever met without this platform?
Unconventional from the start, it all started with a joke about AI that Grimes posted on Twitter – one that impressed Elon enough to slide into her DMs. Fast forward a few years later, the couple now has two children with rather unique names: X Æ A-12 and Y (Exa Dark Sideræl Musk).