The odd couple! The strangest celebrity pairings of 2023

They called it the summer of mismatched love. They said they would never last. For many, it was true. And yet, the odd couples of 2023 persist.

It started, in what now feels an age ago, with Taylor Swift and Matty Healy of The 1975 back in May, a relationship that upset and deeply disturbed many. Then it only got more random: Bill Murray and Kelis. Avril Lavigne and Tyga. Leo DiCaprio and Gigi Hadid. The matrix was clearly malfunctioning.

All of these odd couples have since called it quits, but much like a head of Hydra, you can cut one off, but two will grow back. If there was a year that proved the opposites attract theory, 2023 was that year. Whether it proved that opposites equals longevity is another question.

So for the curious, or the forgetful, here are some of the weirdest couplings (or rumoured couplings) of the past year.

The relationship that once sounded like it came straight out of a TMZ headline generator has had a strangely enduring staying power this year, with rumours first circulating about the pair “hanging out” around April. A lot has happened since then — sources telling People they were just “getting to know each other,” sources telling People that they were actually “not serious”, breakup rumours, reunion rumours. Lots of words, and very little pictures for two of the most photographed young celebs on the planet. For a while, the best we got was a blurry picture of Kylie and Timmy T walking next to eachother in a garden, which did little to calm our curiosity.

Now, finally, the pair are gingerly tip-toeing out into the light of the paparazzo bulbs. First, they appeared at Beyoncé's Renaissance tour in LA together, where they were spotted doing everything short of heavy petting. Then, they appeared equally loved up (though a little more reserved in their affections) at the US Open. And last month they were seen at WSJ Magazine’s 2023 Innovator Awards together, their first outing official as a "fashun" couple, though they arrived on the red carpet separately.

Yet for all the evidence it still feels a little off. As someone on Twitter put it back when the rumours first started circulating: “Kylie Jenner and Timothée Chalamet dating feels like the same as when two people from your high school that never interacted start dating like six years after graduation.”

Still together? Yes.

Yes... chef? After two very high profile break ups — with Rauw Alejandro and Addison Timlin respectively — these two quickly became hot property on the singles market. Allen White is the star of 2022 and 2023's hottest TV series, The Bear, and Rosalia is the two-time Grammy award winner shaking up the music scene. But no one expected these two together.

It all came out when Allen White was photographed with the Spanish singer at an LA-based flower market in October, then later in a parking lot at the start of December. We're not entirely what the pair have in common other than fame and fumar (smoking) but who knows, maybe they're onto something. Maybe we should let 'em cook.

Still together? Yes.

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 everywhere from 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 may perhaps help explain his 2023 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 earlier this summer and The Sun revealed they were dating not long afterwards.

It was a shortlived summer romance, with sources telling the US Sun it has already come to an end. “Kelis and Bill were — and still are — very fond of each other but things just ran their course,” a source told the outlet. “They both have busy schedules and after a whirlwind romance decided to go their separate ways. They hope to remain friends but also plan to get on with their lives.”

Still together No.

Now this one is very much a rumour, but the pair were spotted on a date together in early December and people cannot wrap their heads around it. It's come as quite the surprise on social media that the Saltburn actor and former Disney star might be involved, especially because few people were aware that the dad-of-one had split from former partner Alyson Sandro. There's a six-year age gap, with Keoghan aged 31 and Carpenter 24, but considering Leonardo DiCaprio is further down this list, that's hardly a whopper.

Still together? They appear to have just started dating, so let's see.

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).

The couple stayed together until late June, when it was revealed they had called it quits.

Still together? No.

Taylor Swift has it harder than most when it comes to relationships. Or rather, how they’re deconstructed in the press. This one might have deserved its fair share of shock and awe, though. The controversial frontman of The 1975 is a divisive figure, and Swift is the world's sweetheart.

The pair only dated for two months before moving on to far more fitting partners: he with model and former Nasty Cherry band member Gabriette, who seems better suited to Matt Healy from the words in that sentence alone, even if you know nothing about her. And she with Kansas City Chiefs player Travis Kelce. It's giving cheerleader and quarterback, and it seems to be working out well.

Still together? No.

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. Unlike most of the other couples on this list, they appear to have stuck it out. In a recent interview with Harper’s Bazaar España, Bellucci told the outlet: “I found in Tim [Burton] a wonderful spirit. I met a spectacular soul.”

Still together? Yes.

Though neither party ever officially confirmed they were dating, we were invested. And apparently so were they at one point: This summer, 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 she would be the first woman over 25 the actor has dated. With personal growth, you have to start somewhere, I guess. Baby steps.

Sadly, they truly were just baby steps, and the links between the pair simmered down over the summer. He is now confirmed to be dating model Vittoria Ceretti, who recently had to watch Leo rap at his own birthday party. Maybe Gigi dodged a bullet.

Still together? No.

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).

The pair were linked in March but had split by May, which is starting to cement a pattern that opposites may attract, but only for so long.

Still together? No.

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.

Still together? Yes.

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.” It's unknown if the pair are still together, but we've yet to hear any break up confirmations.

Still together? Unknown.