From Kim Kardashian and Nick Cannon to Madonna and Michael Jackson, there are some random Hollywood couples that happened in the past, but still, confuse us to this day. Prepare for nostalgia lane cause we're taking it back.
Serena Williams & Drake
Based on his lyrics, Drake proved he can tap into his emotions when he wants to. That's likely what lead to his former fling with Serena Williams. Yes, Rewind to 2011, and the tennis champion had cozied up with the rapper.
Chatter spread when Drake was seen on the bleachers supporting Williams. But a line from his 2013 hit, Worst Behavior, later confirmed listeners' curiosity. "Tennis matches at the crib…swear I could beat Serena," he rhymed. While neither admitted to their connection, their lingering eye contact and appearances spoke for them.
Janet Jackson & Matthew McConaughey
What does one get when crossing a singer-songwriter with a Texas boy turned actor? If we're talking about the 2000s, the answer is Janet Jackson and Matthew McConaughey as an item! When McConaughey met Jackson, he became infatuated with the contemporary R&B vocalist. But their story didn't end there…
If their union seems a bit foggy, that's okay. "We went and had dinner one night. That was sorta it," Matthew admitted on Watch What Happens Live. "It was just for a minute; that's why I am so hesitant to mention it," Jackson later commented. While their date may have ended that night, it'll go down as a historical one in our book.
Kate Beckinsale & Pete Davidson
After Pete Davidson's rollercoaster relationship and engagement with Ariana Grande, he began a possibly even more puzzling relationship with a woman 20-years his senior. Davidson and Kate Beckinsale began dating in 2019, but this was yet another short relationship for the stand-up comedian, as they split 4 months later.
"It's all quite shocking and something to get used to," Beckinsale admitted about the adventures of her past relationship. From cozied-up dates to their large age difference, the British actress and Pete were certainly a confusing pair. But they're not even the most surprising on our little list...
Brenda Song & Macaulay Culkin
Kid actors Brenda Song and Macaulay Culkin have more in common than we might have believed, especially now that they've created a little addition to their family! Even after casting them together in his production, Changeland, director Seth Green said he "Didn't see that one coming."
Yet, the happy couple seems to be madly in love and utterly amazed by each other. Along with heartfelt pictures on her Instagram, Song posted about the My Girl actor; "My unicorn that I never thought could exist, I am [the] luckiest person in the world because I am loved by you."
Cher & Tom Cruise
Tom Cruise and Cher. Yes, that's right. And no, we didn't see that one coming either! Let's rewind to 1985 when the iconic singer and Mission: Impossible actor first met each other at the wedding of another interesting couple, Madonna and Sean Penn. Aside from their haute style, they soon learned they had much in common.
"I was so crazy about him. He was so wonderful," Cher gushed of her memories with Cruise, who she quickly labeled one of her "Top five lovers." This was another couple with a significant age difference, 16 years to be exact, but that didn't seem to keep 23-year-old Cruise or 38-year-old Cher's hands to themselves.
Chelsea Handler & 50 Cent
50 Cent might put off a tough persona on the outside, but according to his former girlfriend, Chelsea Handler, he's actually a "Big fat teddy bear." After appearing on the Chelsea Lately stage 10 years ago, the rapper did whatever it took to catch Chelsea's eye. And, based on Handler's testimonials, his efforts weren't in vain!
So, how did the In Da Club artist win Chelsea over? "He started sending me flowers - but ridiculous amounts of like 50 white roses," Chelsea revealed. The rapper must have had a good florist because the pair went on to date for several months before ultimately splitting ways.
Kim Kardashian & Nick Cannon
So, who remembers the good 'ole days of Kim Kardashian and Nick Cannon? Not many? We don't blame you. Back when Kardashian was still employed by Paris Hilton, the reality TV star crossed paths with show announcer Cannon. After dating for a short while, their union ended in 2007.
The world should have known that this was just the beginning of a series of short relationships for Kim, but only time would tell what the future would bring her. The most ironic part of Kardashian and Cannon's relationship? He credits himself for introducing his former other half to Kanye. *Sips tea*
Chelsea Peretti & Jordan Peele
After coming across each other's Twitter profiles, actress Chelsea Peretti and director Jordan Peele got to chatting. We aren't sure who slid into whose DMs first, but after they made things official, things took a turn for the worse. So, what happened next?
Well, after they eloped "A bit ago," as Peretti recalled, the couple has done everything they could to keep their intimate relationship a secret. While we may never find out what happened between their 2016 wedding and now, we can only imagine their marriage is full of laughter and endless comedy-filled days!
Gwen Stefani & Blake Shelton
Adam Levine nearly fell off his chair when his The Voice co-judges, rockstar Gwen Stefani and country singer Blake Shelton, started dating. Well, as they warmed up to each other on and off the show, the couple proved that the right person could be right in front of us all along.
Gwen was just as shocked about their relationship as nearly everyone else. "I never expected that this would be where I'm at," she admitted after Shelton proposed in 2020. According to their social media accounts, it seems that we'll be seeing a rockin' country wedding from them this upcoming summer!
Olivia Wilde & Harry Styles
Harry Styles has stolen the hearts of many throughout the years, but none like his new woman's. The former One Direction singer is off the market thanks to his newly sparked relationship with Olivia Wilde. While fans are equally as shocked as they are obsessed, many remain eagerly curious.
To clear some of the questions about their union up, the couple met on the set of Wilde's most recent movie. As a bonus, we can expect to see Styles in the flick too! While they say they're keeping their relationship on the DL, their outings full of lingering eye contact and hand-holding unquestionably hint differently.
Kourtney Kardashian & Travis Barker
For years, Kourtney Kardashian and Travis Barker have been closer than we thought. The world heard that the switch had flipped from friendship to relationship after they began dating back in February. With many heartfelt posts all over their socials, fans are understandably obsessed.
Despite confused fans, these two have been going strong. On October 17, 2021, they even took things a step further and got engaged! Ever since, the pair have gushed their love for one another all over social media. From matching Halloween costumes to family vacations, the two seem to be very happy.
Bethenny Frankel & Eric Stonestreet
Okay, everyone, brace yourselves for this next couple because this might be the most unexpected union in Hollywood. Introducing Bethenny Frankel of RHONY's and Eric Stonestreet of Modern Family. That's right; unconventional romance doesn't just live on the screen; it happens in real life too!
Although they are no longer together, in 2017, Frankel chatted with Andy Cohen and spilled the tea on her past romances. Namely, her relationship with Stonestreet, in which she admitted they couldn't keep their hands off each other. "She's a wonderful kisser," Stonestreet reminisced.
Holland Taylor & Sarah Paulson
Think what you will about DMs, but for Holland Taylor and Sarah Paulson, it's where their love story began. As it turned out, the couple now thanks Twitter for their doting relationship. Yes, after meeting at a 2005 party, Holland slid into Paulson's DMs, unphased by their 32-year age difference.
It took the women nearly 10 years to make their relationship official, but based on how happy they seem, the wait must have been worth it. "I didn't choose to fall in love with the person I fell in love with," Sarah welled. It seems like the cliché of sliding into the DMs might not actually be such a dire faux pas!
Katie Holmes & Jamie Foxx
Their 11-year age difference aside, Katie Holmes and Jamie Foxx managed to keep their 6-year relationship almost entirely under wraps until they publicly split in August. Prior to their fall-out, the couple shocked many when they arrived at the 2019 Met Gala arm-in-arm. But, things soon drastically changed.
While it remains unknown what caused the First Daughter actress and Jamie to break up, their confusing relationship will continue to confuse people. When did they begin dating? Why was it kept a secret? In the meantime, we're moving on to other celebrity couples that left us equally baffled.
Megan Fox & Machine Gun Kelly
Tattoos, stature, good style, and rhythm aside, there's no denying that Machine Gun Kelly warrants a double-take. However, let's put his impressive abilities on pause for a moment because we're focusing on the artist's relationship with actress Megan Fox.
From bloody-good gifts (IYKYK) to fancy adventures, the couple has not held back from sharing their relationship with their social media followers. "I knew right away that he was what I call a twin flame," Fox confessed on the Give them Lala…With Randall podcast. It seems like Megan has met her match!
Lisa Bonet & Jason Momoa
Jason Momoa lived out many of our adolescent dreams of marrying that kid-crush. Remember? The one who gave you butterflies for the first time? That's right, an age difference of more than a couple of years aside, Momoa not only dated but married his lifelong crush, Lisa Bonet.
The Game of Thrones actor reminisced, "Ever since I was 8-years-old and I saw her on TV, I was like 'Mommy, I want that one.'" So, after they met in person for the first time in 2005, Jason made a move on his long-time wish, and it finally came true. By 2017, the pair were famously married, and the rest is history!
Solange Knowles & Lil Wayne
Here's some tea hotter than Solange's infamous elevator feud with Jay-Z: A supposed secret relationship with Lil Wayne. We'll say that again. Queen Bey's sister and Weezy were apparently an item once upon a time. But, based on who you ask, you might hear different stories completely.
If you ask Solange about the rumors, she'll likely have nothing to say, as she did back in 2007. But Lil Wayne seems to claim a different story. At a Clubhouse feature, the rapper fumbled on his words and started his own rumor that the pair were once an item. In fact, the rapper seemed to think their fling was basic knowledge.
Amber Rose & Val Chmerkovskiy
Remember when Amber Rose took over the stage of Dancing With the Stars? If you need a little refresher, she spent about 6 weeks on the show with her dancing partner, Maksim Chmerkovskiy. But, when she met Maksim's brother Val, things Rose began to spin in a good way.
In 2016, Rose met Val and went on to date for about 5 months before, unfortunately, breaking things off. There's no denying that her famous past relationships with Wiz and Kanye have dominated the tabloids, but there's no way we'll be letting this one slip from our memories!
Jada Pinkett-Smith & August Alsina
Jada and Will Smith have become one of the most well-known couples in Hollywood, but last year, their relationship was put on blast after August Alsina spun a story his own way about the Smith's marriage. As he phrased it, Jada and Will's relationship wasn't what the world thought.
Of his "entanglement" with Pinket-Smith, the rapper admitted, "I truly and really, really deeply loved." But not even their 21-year difference in age was the most shocking part of the fiasco. "[Will] gave me his blessing," Alsina insisted of the brief relationship, which came to fruition while the Smith's secret break was in play.
Rihanna & Travis Scott
Throwback to Rihanna and Travis Scott! Maybe this one slipped from memory, but, not by fault of ours! According to Complex, the hush-hush relationship was purposefully kept as a secret of all secrets. But why? "It's obviously embarrassing," Scott supposedly admitted to writer Lawrence Schlossman.
As Schlossman clarified further, he revealed that Scott said, "It's because Rihanna's like, 'Don't tell anyone that I'm [with] Travis Scott, please.'" According to Travis, the pair were an item in 2015, which might ring a bell from seeing RiRi attend a few of his shows.
Shailene Woodley & Aaron Rodgers
If it seemed that Shailene Woodley and Aaron Rodgers' relationship came out of thin air, you're not alone! Woodley herself was even a bit taken back by its happening. "I never thought I'd be engaged to somebody who threw balls for a living," the Divergent actress playfully joked.
After crossing paths with the NFL star in 2020, what Shailene calls a "Wacky, whacky time," the two experienced a whirlwind relationship almost instantly. Before she knew it, Rodgers got down on one knee and became her boyfriend-turned-fiancé. Touchdown! If there's a power couple we'll be looking out for, it's this one.
Vanessa Valladares & Zac Efron
Imagine this: You're a waitress on the evening shift, waiting for the clock to tell you it's time to go home, when all of a sudden, not just any celeb, but Zac Efron, sits down in your section. Well, that's exactly what happened to Vanessa Valladares. In fact, before finishing his meal that night, Efron asked for her number.
As the fairytale goes, Zac met his aspiring model girlfriend, Vanessa, in 2020 when she served his table at Australia's Byron Bay General Store & Cafe. They began dating, Valladares quit her job, and the pair have been enjoying each other's company on the beach and cozied-up ski trips ever since!
Ciara & Bow Wow
"I didn't know I cared for her until I tried to play her," Bow Wow said of his past involvement with Ciara. While we aren't exactly sure what happened during their 2-year relationship, we do know that it ended in a failed engagement and 50 waves of shade.
Their story starts back in 2004 when the couple stepped out onto the scene. But, 2 years later, things turned South, and their relationship eventually ended in a mess of a separation. "I let things in the past that I know was wrong affect my engagement," Bow Wow admitted.
Evan Rachel Wood & Marilyn Manson
While this couple might not be together anymore, Evan Rachel Wood and Marilyn Manson's names have remained tied. After becoming an item in 2007, things ended on uneasy terms for the singer and actress. They suddenly canceled their engagement without reason until a few years passed when Wood spoke out.
This year, Wood spilled some secrets from her former relationship with the rocker, who's nearly 20 years her senior. According to Wood, Manson had harshly mistreated her, along with many of his other former sweethearts. While we don't know the deets of what happened, we know that the unknown will forever haunt us.
Paris Hilton & Travis Barker
Before Travis and Kourtney took over the media, the Blink-182 drummer was wrapped up with another big star. Now, this is something that shocked us all: Travis Barker and Paris Hilton. Does anyone remember? Well, according to Hilton, there are a couple of things she would like to have left back in 2006 with their fling.
Apparently, while Barker was with Hilton, he had a big crush on her former assistant: Kim Kardashian. Yes, awkward, for sure! "Kim was eye candy. I was [in] no way disrespectful to Paris, but I couldn't keep my eyes off Kim!" Barker admitted. Funny how the tables (and his sights) have turned…
Catherine Paiz & Michael B. Jordan
While now it might seem odd to see Catherine Paiz by anyone's side other than Austin McBroom, believe it or not, back in 2014, she was! Life was different for the YouTuber back then. In fact, Catherine was once linked with Michael B. Jordan. But, neither of them ever verified their former fling.
Even though they've never publicly commented, we can't help but bring attention back to how cozy Paiz and Jordan looked when they were spotted together in Miami. From beachside strolls to playfully racing jet-skis, their getaway seemed pretty romantic at the time.
Bella Thorne & Scott Disick
It isn't new news that Scott Disick's dating track record has been a hot topic both on and off Keeping Up With The Kardashians. But, when he was seen in public, hand-in-hand with Bella Thorne in 2017, people understandably were very curious. But, as it turned out, things weren't as they seemed.
In fact, it really depends on who's answering the question. According to Kendall Jenner, all it took to get the brewing tea was a simple phone call to Disick. "I'm doing it to make Kourtney mad," Disick supposedly admitted to Jenner. But don't take our word for it, keeping up with this family is pretty tricky.
Madonna & Michael Jackson
What does one get when crossing Michael Jackson with Madonna? The answer is a casual date to the Oscars! Apparently, back in 1991, when trying to figure out plans for the award show, "Michael was like, 'Who are you gonna go with?' I looked at him and said, 'I don't know…wanna go?'" Madonna shared.
But did the casual flow continue after the show? Aside from one little detail that Madonna let slip, the world might never know. "You wanna know what happened after that? I'm not gonna tell you," she teased. Years later, during an episode of "Carpool Karaoke," she admitted that they had the "Best date ever," sealed with a kiss!
Kylie Jenner & Tyga
Speaking of the Jenner's, Kendall was actually there for the beginning of her sister Kylie's relationship with Tyga. As the story goes, the pair began dating way before going public. For Kendall's Sweet 16 (when Kylie was only 14,) Tyga performed and caught the younger sister's eye.
Jump to a few years ahead, and the lovebirds hit the world with the news that they were an item. People were understandably a bit shocked, as Kylie was the (literal) baby sister of Kim Kardashian. Their relationship lasted a few years until Tyga turned 26. According to TMZ, Jenner called it quits at his birthday party.
Grimes & Elon Musk
Elon Musk can thank Twitter for two things: The ability to Tweet the oddly exciting thoughts of his mind and allowing him to slide into his now baby-mama's DMs. In fact, if it wasn't for Twitter, the pair may never have linked up. But, we need to rewind a bit more to where this unexpected couple began.
Grimes took to Twitter to post a joke about Artificial Intelligence, causing an impressed Elon to slide into her DMs. Jump to the present-day, and the unconventional couple has had their first child, X Æ A-12 (pronounced Ex Ash A Twelve). All things considered, this couple might be one of the quirkiest on our list!
Kim Kardashian & Pete Davidson
After meeting on the set of Saturday Night Live, rumors began spreading that reality star Kim Kardashian was dating Pete Davidson. Fans of either celeb would have never guessed these two would be in a relationship - but when pictures were released by the paparazzi, it shook the internet.
From ice cream dates to outings in Staten Island, these two have been seen everywhere. Davidson even got Kim to ditch the diet and eat pizza! Most recently, the SNL comedian referred to Kardashian as his 'girlfriend.' Safe to say we never saw this coming, but we have to admit they're pretty cute together.
Ben Affleck & J. Lo 2.0
Back in 2002, Jennifer Lopez and Ben Affleck called it quits, and many fans were disappointed by the news. Little did they know that nearly 20 years later, the duo would find their way back to each other. When they finally rekindled their relationship in 2021, many were surprised.
Luckily we won't have to see them break up again because recently, JLo admitted, "I don't think we would have got back together if we thought that was where it was headed." AKA she, doesn't see an end in their relationship anytime soon… or maybe never?
Anna Kendrick & Bill Hader
Back in 2019, Anna Kendrick met her future beau Bill Hader on the set of the film, Noelle. But as it turns out, they became more than just good friends after starring together. The two actors had started secretly dating, and they were successful for about a year.
Not only did the pairing surprise many fans, but so did the fact that they were able to keep things under wrap for so long! With paparazzi and social media, it seems like these days we know who's off the market at all times. Well, props to these two for making it work.
Kanye West & Julia Fox
Despite many efforts to win back his ex-wife Kim Kardashian, like buying the house directly in front of hers or serenading her during a concert, Mr. West has a new girlfriend. The two made headlines after they starred in an intimate photoshoot for Interview Magazine, where Fox revealed details of their romance.
After meeting in Miami on New Year's Eve, the pair have been spotted together non-stop. Is it another way of trying to get Kim's attention - or is West really in love? We can't be sure. All we know is this was definitely an unexpected turn of events, although can we really be so surprised? After all, it is 'Ye.
Lance Armstrong & Ashley Olsen
The former child star, Ashley Olsen, started dating former professional cyclist Lance Armstrong back in 2007. It wasn't just the random pairing that was deemed odd by fans, but their large age gap. At the time, Olsen was 21 and Armstrong was 36, giving them a difference of 15 years.
Well, it seems it was more than just the public who had an issue with the age gap because apparently, Armstrong's friends encouraged him to break up with the Full House star. That wasn't before the two were spotted on many PDA-filled outings around New York City!
Michelle Rodriguez & Zac Efron
Paparazzi's went crazy when they spotted Fast and Furious star Michelle Rodriguez and former Disney actor Zac Efron all over each other back in 2014. The duo looked like they had a blast spending time together in Ibiza, Spain. But this pairing was unforeseen by fans.
Efron and Rodriguez might have been an unexpected celeb couple - but it didn't last too long since after 2 months together, they had already called it quits. Was it possible that it was just a summer fling between the stars? Or maybe they couldn't handle the 9 year age difference? We can't be sure.
Justin Timberlake & Fergie
When Justin Timberlake was 16 years old and rising to fame, he started dating a fellow celeb, Fergie, who at the time was 23. The former Black Eyed Peas singer admitted that the two had a short-lived fling back in the late '90s - all while her then band Wild Orchid was on tour with NSYNC.
Although the relationship didn't last long, spectators were concerned about the age gap, especially since Timberlake was still a teenager. Nearly a decade later, Fergie was asked about it during an interview with Watch What Happens Live With Andy Cohen. She responded with, "It wasn't all that serious."
Lenny Kravitz & Nicole Kidman
Back in 2002, singer Lenny Kravitz was Nicole Kidman's landlord when they formed a relationship with one another. They kept things private and away from the public eye - even having been engaged without fans knowing! Kidman explained why they never tied the knot: "I wasn’t ready. We weren’t ready."
Funny enough, Kravitz's daughter Zoe ended up being co-star's with Kidman in 2017. Zoe told 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 it wasn't official, rumors began spreading around the 1990s that these two famous singers had started dating. It seemed like an odd pairing between the hip-hop artist and pop diva icon. It wasn't until 25 years later that Madonna revealed the truth about the rumors.
Madonna admitted, "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." Later on, a handwritten letter from Tupac to the singer was leaked, which gave fans more insight into their relationship.
John Mulaney & Olivia Munn
After John Mulaney and his wife of 6 years divorced, he was quick to move on. Fans weren't sure how this relationship came to be, and they were stunned to find out the SNL comedian had started dating actress Olivia Munn. It was arguably one of the least expected celeb couples of the year.
Many were concerned since Mulaney had been struggling with substance abuse and fans feared that a new partner would set him off track. Despite this, the two continued dating and even announced they were expecting a child together, who they welcomed in December 2021!
Channing Tatum & Zoe Kravitz
In early 2021, Zoe Kravitz and Channing Tatum sparked dating rumors after they were spotted hanging out. At first, they denied the allegations, but later on that year there was no hiding their love. With many paparazzi pics filled with PDA, it was clear they were in a relationship.
In September, they even attended one of the most celebrity-filled events of the year together - the Met Gala in New York City. While in the beginning, the internet found the two celebrities to be an unexpected duo, now they have many fans rooting them on.
Hunter Schafer & Dominic Fike
Fans of Euphoria know that romance is a current theme on the show. And now it looks like some of those sparks have made their way off-screen. While on the HBO series, characters Jules and Elliot aren't an official couple, they seem to have sparked rumors that in real life, they may be in a relationship!
Hunter Schafer and Dominic Fike were seen holding hands, walking out of a restaurant, The Nice Guy, in LA. A day later, Fike created more buzz surrounding the idea of the two being together when he posted Schafer’s Jimmy Kimmel Live! interview on his Instagram. Was he supporting his possible girlfriend or just cheering on a co-star?
Macaulay Culkin & Mila Kunis
Before Mila Kunis and Ashton Kutcher were married with two kids, the That 70's Show star was in a long-term relationship with fellow actor, Macaulay Culkin. The Home Alone actor and Kunis were together from the year 2002 till 2011 when they broke things off.
Back in 2009, during an interview with Women's Health Magazine, she confessed, "We grew up together." When they started dating, Kunis was 18, and Culkin was 21. "You find a steady rock in your life, and that's all you need. We have our ups and downs, but work through them."
Daryl Sabara & Meghan Trainor
In 2016, Meghan Trainor was set up on a date with Daryle Sabara by their mutual friend, Chloe Grace Mortez. It seems like Mortez was a good matchmaker because the two really hit it off! When news broke that the All About That Bass singer was dating the boy from Sky Kids, fans were shocked.
Who would have ever guessed that these two stars would ever cross paths, let alone end up getting married! They even welcomed their first child together back in 2021. Today Trainor and Sabara seem to be happy, posting many TikToks together for fans (including us) to enjoy.