The odd couple! 9 of the strangest celebrity pairings

They say love is blind. Whoever came up with the line, clearly, had never been privy to someone furiously vetoing potential matches on Hinge. Decoding someone’s ‘interests’ section on a dating app to decipher a stranger’s entire personality, relationship history and, ultimately, likelihood of being a partner you could happily tolerate. It’s the age-old compatibility test.

How much do we have in common? Is being into hard rock a hard pass? Are they my type on (virtual) paper?

Though it would appear these ridged rules of attraction are losing their appeal in 2023. Making room, instead, for the summer of (mismatched) love. Untyping. Rewriting romantic scripture a la Bill Murray, 72, and Kelis, 43 (see below) – whose who-would-have-guessed-it coupling, according to recent reports, caused the Twittersphere to do a double-take (“Kelis and WHOMST?!”) today. Like when I reminded a friend on WhatsApp that Cher and Tom Cruise had a thing in the 1980s: “wtf.”

So, for the OAC (opposites attract curious) gathered here today: let’s that a closer look at some of the most, at first glance, perplexing celebrity pairings of late.

Kelis and Bill Murray

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Admittedly, Bill Murray has a certain charm. For one, and it’s a big one, he’s funny as hell. Lesser-known trivia about the Lost in Translation actor is he’s a huge jazz fan and has even played surprise pop-up performances in NYC hotels to Greece. “I felt like this old Shakespearean actor at the turn of the 20th century, down there in New Orleans, playing shows for people,” he said in a Rolling Stone interview. Which perhaps explains his reported new romance with Kelis. The Kelis. My milkshake brings all the boys to the yard, Kelis. The actor was spotted watching the R&B singer at Mighty Hoopla festival last weekend. Random, perhaps. Even random-er? Hollywood stars bopping around Brockwell park.

Timothée Chalamet and Kylie Jenner

ES Comnposite

Again, this is very much internet hearsay. Though the pair have been (blurrily) pictured together on several occasions over recent months, after celebrity gossip hinterland, DeuxMoi, alerted us to Kimothée rumours. So far, so mysterious. Still, the dating commentary floweth. According to one tweet, “kylie jenner and timothee chalamet dating feels like the same as when two people from your high school that never interacted start dating like 6 years after graduation.”

Avril Lavigne and Tyga

Getty Images

While the hard launch had a (brief) moment at the start of the year it seems we’ve gone back to basics. In May, the Sk8ter Boi singer posted an innocent ‘Lyfe lately’ carousal on Instagram featuring mostly filtered selfies sandwiched between a picture of her embracing award-winning rapper Tyga (the pair sparked headlines of new romance when they had dinner back in February at Nobu). A question, we’ll likely never know the answer to: are they fans of each other’s music?

Taylor Swift and Matt Healy

ES Composite

Taylor Swift has it harder than most when it comes to love. Or rather, how they’re deconstructed in the press. As though who she’s dating is somehow a personality trait, the most important aspect of self, merely because her songs draw from her relationships. Still, her devoted fans were not happy with news that she was hooking up with 1975 frontman Matt Healy. A name that divides many. They apparently split after two months dating. She’s said to be ‘doing great.’ No bad blood.

Cher and Alexander ‘AE’ Edwards

AFP via Getty Images

No shade on Cher. We love you. The songs, enthusiastic tweets, telling your mother you’re a rich man, even your inconsistent taste in men (from Sonny Bono, Tom Cruise, a bagel maker to a music executive, Alexander ‘AE’ Edwards, 40 years your junior).

Monica Bellucci and Tim Burton

AFP via Getty Images

She’s an Italian goddess. He’s the godfather of macabre moviemaking. The guy has form: having had a 13-year relationship with the mythically beautiful Helena Bonham-Carter. The pair were spotted kissing earlier this year and have reportedly been dating for months. Hey, stranger things have happened.

Leonardo DiCaprio and Gigi Hadid

PA

Though neither party has officially confirmed they’re dating, we’re invested. This week the supermodel was spotted meeting Leo’s father and stepmother. Which, as anyone knows, is code for: This Is More Than Just A Hang. What’s strange, however, about the coupling is the numbers game: if the rumours are true, at 28 years old it would be the first woman over 25 the actor has dated. With personal growth, you have to start somewhere, I guess. Baby steps.

Lady Kitty Spencer and Michael Lewis

German Larkin / via Instagram

Princess Diana’s niece, Lady Kitty Spencer, 31, made headlines when she announced her engagement to South African multi-millionaire businessman, Michael Lewis. At 61, Lewis is five years younger than her father, Charles Spencer. In a twist of events, when the pair married in a 17th century Roman Villa in 2021, the father of the bride was absent. Cue conspiracy theories. Though it is a trend, he also skipped his daughter Lady Amelia’s wedding this spring. To be fair to him: weddings are a logistical hellscape. So, there’s that.

Madonna and Joshua Popper

Instagram

Are normcore boyfriends a thing? According to Madonna, apparently so. The 64-year-old hitmaker is now making moves with 29-year-old boxing coach, Joshua Popper. She’s aware of the age-gap optics and fundamentally does not care if this irks people. “I have lovers who are three decades younger than me,” she shared in a 2017 interview with Harper’s Bazaar. “This makes people very uncomfortable. I feel like everything I do makes people feel really uncomfortable.”

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