Hollywood? More like Holly’s dating WHO?!
Tinseltown brings together some of the most… erm… eccentric folk from around the world. So with all that energy clustered into one space, sparks are bound to fly, right? Even if they’re sorta sparks you’d never, EVER imagine to fly… Like, the most random sparks you wouldn’t conjure up in your wildest dreams, LOLz!
Related: Celeb Couples With The Biggest Age Gaps
But hey, opposites attract! And this list of The Most Random Celebrity Couples is proof! Starting off, we have..
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- 1 Kim Kardashian & Pete Davidson
- 2 Sydney Sweeney & Scooter Braun
- 3 Gwen Stefani & Blake Shelton
- 4 Tyga & Avril Lavigne
- 5 Chelsea Handler & 50 Cent
- 6 Bill Murray & Kelis
- 7 Brigitte Nielsen & Flavor Flav
- 8 Kylie Jenner & Timothée Chalamet
- 9 Cher & Alexander “AE” Edwards
- 10 Scarlett Johansson & Jack Antonoff
Kim Kardashian & Pete Davidson
Kicking off our list, we present you a couple that shocked EVERYONE when they first hooked up: Kim Kardashian and Pete Davidson! No one would have ever paired this couple — Kim, a 40s-something mother-of-four fresh off a divorce from Kanye West who’s built a whole EMPIRE on looking perfect, and Pete, a 20s-something stand up comedian with a proclivity for the high life and raunchy jokes. While their relationship didn’t even end up lasting a full year, it was enough to shock the globe. But NO one was more upset about it than Ye! Ha!
Sydney Sweeney & Scooter Braun
When ranking hot button couples, we’d be remiss to mention Sydney Sweeney and Scooter Braun! They’re literally two of the most controversial figures in Hollywood today, so when fans found out they’d come together, it was open season in the roasting department! Who would have expected Sydney — who broke off an engagement this year and has widely been linked to Glen Powell — would end up dating the dude who sold off all Taylor Swift‘s master recordings?? Not us!
Gwen Stefani & Blake Shelton
OK, if we’re talking random celeb couples, there’s no WAY we could leave Gwen Stefani and Blake Shelton off the list. We mean, who would have ever thought the artist who sings Just A Girl, known for her signature punk style, would go on to date AND MARRY the guy who sings God’s Country?? We don’t know what’s more random — the fact that they got together in the first place, or the fact that it wasn’t just a smash and pass!
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Tyga & Avril Lavigne
If we’re talking punk princesses, we can’t go without naming Avril Lavigne. Who would have EVER thought she’d go on to date Kylie Jenner’s ex, rapper and OnlyFans model Tyga??? The pairing just seemed SO out of left field when romance rumors first flew in early 2023! But we all know opposites attract… And as she once sang in Sk8er Boi, “He was a boy, she was a girl. Can I make it anymore obvious?” We guess it really is that simple!
But while they may have burned bright for several months, the artists ultimately called things off for good in October of that same year. You just had to be there!
Chelsea Handler & 50 Cent
At the height of Chelsea Handler‘s talk show success in 2009, she managed to land one of the hottest rappers at the time for a chat: 50 Cent. And at the time, their chemistry was VERY apparent! We mean, just ch-ch-check out this clip (below):
And two years later, the pair made things official! Well, somewhat official. They mostly kept things casual until things eventually fizzled out, but Chelsea still to this day has nothing but nice things to say about the Candy Shop rapper. In 2020, she even dedicated an Instagram post to her “favorite ex.” HA! See (below):
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And during an appearance on the Call Her Daddy podcast earlier this year, she gushed:
“He was beautiful, he was a sweetheart, he was so sweet. “
Very cute!
Bill Murray & Kelis
Bill Murray and Kellis are not only a random pairing, but also ripe for another famous list of ours: Celeb Couples With The Biggest Age Gaps! No one expected the 75-year-old actor to sweep the 46-year-old singer-songwriter off her feet, but that’s exactly what he did! Or, that’s at least what a lot of people believe.
The rumors came pouring in in 2023 when the unlikely pair were spotted hanging out, but by the end of summer, sources claimed the Milkshake singer dumped the Ghostbusters star. Neither ever really publicly addressed the alleged romantic fling… until earlier this year! In March, Bill kinda-sorta denied they were ever actually together to begin with. He claimed on SiriusXM‘s Sway in the Morning:
“I met this girl named Kelis. I got great press that I was dating her. That really raised my cred a lot.”
LOLz! Random for sure!
Brigitte Nielsen & Flavor Flav
Next, we present you with some straight up reality TV royalty: Brigitte Nielsen and Flavor Flav! The Danish actress and the rapper both appeared on The Surreal Life in 2004, and sparks FLEW for the pair. So much that their unexpected romance became the subject of a brand new reality TV show of their own called Strange Love, which doubled down on the bizarre pairing! Watch a promo clip (below):
Kylie Jenner & Timothée Chalamet
Before 2023, no one would have EVER uttered Kylie Jenner and Timothée Chalamet‘s names in the same sentence. We mean, they come from completely different worlds… she’s from reality TV, and he’s from prestige filmmaking. Can we make it anymore UN-obvious?? Wait, that’s Avril’s line! We guess she and Kylie do share Tyga in common… LOLz!
ANYWAYS, rumors that Kylie and Timmy were dating began circulating in early 2023, but they didn’t confirm things until September of that year when they were spotted at a Beyoncé concert together. But they’ve definitely been keeping their relationship intentionally on the low. He’s yet to appear on her reality show The Kardashians, and while she’s accompanied him to multiple awards shows, they’ve only posed on a red carpet together ONCE. And still no Instagram posts featuring each other! There’s even speculation they’re hitting the end of the love road, but nothing confirmed yet. We guess they’re just the mysterious type…
Cher & Alexander “AE” Edwards
Like Bill and Kelis, Cher and Alexander “AE” Edwards fit this list AND the Celeb Couples With The Biggest Age Gaps list. Who would have thought that at nearly 80 years old, the Believe singer would have bagged a hottie in his 30s?? Actually, we take that back. She’s fricking CHER, man! Who WOULDN’T have suspected that??
The icon first started dating Amber Rose‘s baby daddy in 2022, and while they’ve been sort of off-again, on-again, they seem to be going strong now! And have even been spotted hanging with Tyga! Man, that guy just knows everybody! LOLz!
Scarlett Johansson & Jack Antonoff
To conclude our list, we present a couple probably NO ONE knew about: Scarlett Johansson and Jack Antonoff! We know what you must be thinking: “WHAT? They dated?! Did I miss the memo?” Well, yes and no. While the two have crossed romantic paths in the past, it was BEFORE they were major celebs… Like, back in their high school days! See (below):
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OMG, right?!
All the way back in 2001, the pair attended Professional Children’s School together in New York City and even went to prom together, as you can see in the photos above! How cute is that?!
So, what do YOU think of our list of The Most Random Celebrity Couples, Perezcious readers?? Be sure to let us know and shout out any we missed in the comments down below!
[Images via NBC/YouTube, Gwen Stefani/YouTube, & PNP/MEGA/WENN]
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