There’s so many celebrity romances we can’t keep track (Picture: Patrick McMullan/Patrick McMullan via Getty Images)
It’s fair to say nobody had A-List couple Kylie Jenner and Timothée Chalamet on their bingo cards but over the years there have been some even weirder celebrity couples.
The baffling world of celebrity means people who would never meet in the real world end up going on nights out together such as Harry Styles and Stephen Hawking – although we don’t believe they dated.
We all make questionable choices when it comes to love but unfortunately for our favourite famous faces, these romances live on in pop culture history.
Kylie Jenner and Timothée Chalamet were not an expected couple (Picture: Getty Images)
Tyga and Avril Lavigne
Tyga and Avril Lavigne briefly dated this year in a baffling link up (Picture: Stephane Cardinale – Corbis/Corbis via Getty Images)
Starting off this list strong because we all need to revisit this, we as a society moved on from this pairing far too soon.
Skater Boy icon, Avril, has one of the most random dating histories ever spanning from her marriage to Nickelback’s Chad Kroeger to Brody Jenner.
This February, she split with American rapper Mod Sun, having been engaged for a year after they started dating in 2021.
After a whirlwind romance, the couple made the mutual decision to split in June with an insider saying the relationship has simply ‘run its course’.
Together no more but always in our hearts, this strange three-month romance will never be forgotten.
Cher and Tom Cruise
In one of the most bizarre couplings, it’s Tom Cruise and Cher (Picture: MCaulfield/WireImage)
Cher was 38 at the time to Tom’s 23 and had already been married and divorced twice when the pair hit it off.
There are very minimal details on this one but in 2013, Cher went as far as to label the actor as one of her ‘top-five’ favourite lovers ever during a chat with Andy Cohen.
She admitted: ‘He wasn’t a Scientologist then. It was pretty hot and heavy for a little minute. He’s a great guy. The person that I knew was a great and lovable guy.’
Emily Ratajkowski and Eric Andre
This romance was hard launched with a naked snap of Eric Andre and Emily Ratajkowski(Picture: Gotham/GC Images)
In a baffling moment that nearly broke the internet, Emily Ratajkowski and Eric Andre posted *that* X-rated Valentine’s Day photo last year.
The comedian appeared to be Emily’s second flame since she split from husband Sebastian Bear-McClard in September 2022.
She had also been linked to SNL star Pete Davidson in November but her brief ‘situationship’ with Eric turned a few heads after he posted the naked picture of them both to his Instagram.
In an interview, Eric claimed he and the 31-year-old runway star thought the snap was ‘iconic’ and simply had to be shared with the world.
‘Emily popped up and took that picture. I was really in the moment, I was drinking wine, she started dying laughing, and she was like, “I have to take a picture of this”,’ said the comedian.
Unfortunately, days after the snap was posted, Emily hinted that she and Eric had called time on their romance in a cryptic Instagram story.
Alanis Morrisette and Ryan Reynolds
Before his Deadpool fame Ryan Reynolds was engaged to singer Alanis Morissette (Picture: Albert L. Ortega/WireImage)
The Canadian duo met at a party hosted by Drew Barrymore two years earlier and graced red carpets with so much PDA we’re shocked they ever broke up.
Sadly they called off their engagement in 2006 … before getting back together and breaking up again two years later.
‘They remain close friends and continue to have the utmost love and admiration for each other. They ask that their privacy be respected surrounding this personal matter,’ their reps shared in a statement to People at the time.
Her 2008 album, Flavors of Entanglement, addresses their fallout, especially with her track Torch and told Access: ‘It’s really about my grief.’
Ryan is now famously married to Gossip Girl icon Blake Lively, sharing three children together.
Keira Knightley and Jamie Dornan
The 00s saw Keira Knightley and a yet-to-be-famous Jamie Dornan get together (Picture: Dave Hogan/Getty Images)
Not even sure where to start with this crossover but yes, the Love Actually star and Fifty Shades of Grey actor dated for two years.
At this point, a relatively unknown Jamie hadn’t even starred in his breakout film role – 2006’s Marie Antoinette – but was making his name known as a model.
Keira, however, was on an upward streak as she had been in hit films like Bend it Like Beckham, Phantom Menace, and of course, Christmas hit Love Actually.
The relationship remained a secret until after they had broken up, with the A Haunting in Venice actor saying he had felt ‘pressure’ by the high profile nature of it.
Emma Roberts and Chord Overstreet
Gleeks were inconsolable as Emma Roberts and Chord Overstreet had a wild relationship (Picture: Charley Gallay/WireImage)
The turbulent Ryan Murphy crossover relationship started in 2011, breaking up and getting back together regularly over the course of the next year.
Apparently, they couldn’t keep their hands off each other as she visited him in London following the Glee Live! Tour, going public during a walk in the park.
Bliss didn’t last long though as at the time the romance was called ‘really immature’ by a source speaking to Star magazine, who added the pair were constantly fighting.
In a random turn of events, the pair were spotted together in 2020 seeming amicable as they attended a party as friends.
Chord was also spotted with another famous Emma in 2018 – Harry Potter’s Emma Watson – although the romance ended after six months.
Renée Zellweger and Bradley Cooper
Renée Zellweger and Bradley Cooper reconciled in 2020 (Picture: Kevin Winter/Getty Images)
The movie was actually made in 2006, but stayed in post-production for three years, leading to a little reconnection and romance in 2009.
Renée Zellweger had also dated Jim Carrey at this point in another bizarre couple.
She and Bradley stayed together until 2011 but kept things super private despite invasive paparazzi pictures plaguing them constantly.
They reconnected once more in 2020 at the Oscars, happily chatting away and smiling so clearly things are perfectly civil.
Vanessa Hudgens and Josh Hutcherson
Teenage girls in their 20s are shaking over this one – Josh Hutcherson and Vanessa Hudgens dated!(Picture: Donato Sardella/Getty Images for HL Group)
Little do fans know, she also dated another Hollywood heartthrob – Josh Hutcherson.
Hunger Games legend and the High School Musical star dated at some point during their time filming 2012’s Journey 2: The Mysterious Island.
While the duo isn’t a wild leap to believe, the awkwardness around their breakup makes for a very strange romance indeed.
When asked if they were dating on the Today show in Australia, the silence was deafening until Josh uncomfortably answered: ‘We’re not… No. We were at one point, but she broke my heart.’
Realising what he said, Josh recovered and added: ‘I’m just kidding. That was a while ago, we’re just really good friends now.’
Katie Holmes and Jamie Foxx
Jamie Foxx and Katie Holmes were secretly together for six years (Picture: Kevin Mazur/MG19/Getty Images for The Met Museum/Vogue)
She began the relationship after finalising her divorce from Tom Cruise in 2012, who she had married in 2006.
They decided to go public in 2015 but still kept things very private.
It wasn’t until 2019 that they decided to walk Met Gala red carpet together, posing for photos and smiling for the crowds.
They left the high-profile event in a limo together, with snaps shared by designer Zac Posen – however, three months later things had soured and the pair had parted ways.
Kim Kardashian and Pete Davidson
Pete Davidson somehow pulled Kim Kardashian (Picture: Gotham/Getty Images)
He has also dated Ariana Grande, Kate Beckinsale, Phoebe Dynevor, and Emily Ratajkowski, gaining a reputation for being one of Hollywood’s most random but irresistible crushes.
Despite calling it quits in August 2022, the bombshell and the former Saturday Night Live star parted amicably with sources at the time citing business as the fault in their romantic stars.
Florence Pugh and Zach Braff
Florence Pugh has defended her age-gap relationship with Zach Braff (Picture: Max Cisotti/Dave Benett/WireImage)
The Scrubs star and the Don’t Worry Darling actress seemed to be heading down a serious road as they adopted a dog together during quarantine.
However, in September 2022 Florence revealed they had split in private a few months prior.
The low-key former couple are said to be amicable after the break-up, highlighted by a message Florence posted hitting out at haters over their large age gap.
She said: ‘I am 24 years old. I do not need you to tell me who I should and should not love and I would never in my life tell anyone who they can and cannot love. It is not your place.
‘The abuse that you throw at him is abuse that you are throwing at me, and I don’t want those followers. I do not want to have to be protecting my comments every time I post a picture of him. I really hope that I can continue this relationship with a lot of you.’
Janet Jackson and Matthew McConaughey
Janet Jackson and Matthew McConaughey had at least one dinner date (Picture: KMazur/WireImage)
They met in 2002 backstage at the Grammy awards and clearly hit it off, spending some time together in a more private setting.
‘We went and had dinner…that was sort of it,’ said Matthew admitted in 2019 on Watch What Happens Live.
Janet was a little more candid about their brief fling, saying in 2006: ‘I guess we did date… It was just for a minute; That’s why I am so hesitant to mention it.’
Madonna and Tupac
Ending on a wild one – Madonna and Tupac Shakur were utterly in love (Picture: Patrick McMullan/Patrick McMullan via Getty Images)
However, Tupac Shakur and Madonna feels like a fever dream but we promise you this happened.
In 2017, TMZ posted a three-page love letter Tupac allegedly wrote to Madonna from prison in 1995, breaking up with her over her race.
The letter read: ‘But for me at least in my previous perception I felt due to my “image” I would be letting down half of the people who made me what I thought I was. I never meant to hurt you.’
Madonna did go on the record and confirmed their relationship in 2015, she told David Letterman: ‘I was dating Tupac Shakur at the time, and the thing is he got me all riled up on life in general. So, when I went on the show, I was feeling very gangsta.’
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