Unexpected Celebrity Couples We Never Saw Coming
When a new celebrity couple makes headlines, we want to know all the details: how they met, how serious they are, and more. Most of the time, we can see a couple coming from a mile away. From the interviews, Instagram comments, or co-starring in a new show we’re obsessed with, we have an inkling that romance may be on the horizon. But every once in a while, there’s a couple that makes us go: “What?! How did that happen?”
Over the past couple years, celebrities have kept us guessing when it comes to their love lives. Stars like Kim Kardashian and Pete Davidson, Ali Wong and Bill Hader, and Emily Ratajkowski and Eric Andre blew our socks off with romance that felt totally out of left field.
While some star prove that opposites attract, others let their shocking romances fizzle out just as quickly as they started.
Whether it was a couple we daydreamed about being one-half of in the ’90s or one that we’re still trying to figure out today, check out the most unexpected celebrity couples below.
A version of this article was previously published in December 2021.
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Rosalía & Jeremy Allen White
2023 was truly the year of the unexpected romance! Shortly after Jeremy Allen White ended his marriage to wife Addison Timlin and Rosalía split from fiancé Rauw Alejandro, these lovebirds were spotted on a date in October 2023.
The couple have had a PDA-filled romance and we love it!
Travis Kelce & Taylor Swift
No one quite expected football star Travis Kelce and musical icon Taylor Swift to start dating, but 2023 was been full of surprises. They started in the summer of 2023 and didn’t wait long to go very public when Swift supported Kelce and the Kansas City Chiefs at several games before showing off some major PDA at the Super Bowl in February 2024.
Ali Wong & Bill Hader
When Ali Wong split from husband Justin Hakuta months before Bill Hader’s relationship with Anna Kendrick ended, nothing could have prepared us for the former Angry Birds co-stars to start dating by the end of the year.
Though they did briefly split, they rekindled things at the end of 2023 and made their love very public during 2024’s award show season.
Timothée Chalamet & Kylie Jenner
Timothée Chalamet and Kylie Jenner have been quietly dating since early 2023 and are slowly proving that opposites do attract but we had a hard time believing the rumors until shortly before THAT U.S. Open PDA session.
Jamie Foxx & Katie Holmes
We never saw Jamie Foxx and Katie Holmes’ years-long romance coming mainly because we never saw it at all!
This ultra-private pairing dated for SIX YEARS without ever speaking about their romance publicly or going out in public all that much before calling it off in 2019.
Pete Davidson & Kim Kardashian
Pete Davidson proved himself to be exactly what Kim Kardashian needed after her January 2021 split from Kanye West.
The couple started dating in October of that year after meeting on set of Saturday Night Live and didn’t hold back the PDA on Instagram, on the Met Gala red carpet and on just about anywhere the paparazzi could catch them until their August 2022 split.
Sandra Bullock & Ryan Gosling
This often-forgotten romance began in 2001 when Sandra Bullock and Ryan Gosling starred in Murders by Numbers and we seen on an apparent date the following year.
Their romance ended shortly before the pair reach the two-year mark but the exes did make headlines in 2011 when Gosling called Bullock and ex-girlfriend Rachel McAdams two of “greatest girlfriends of all time.”
Ethan Slater & Ariana Grande
All in one shocking month in July 2023, Ariana Grande split from husband Dalton Gomez and was rumored to have moved on with Wicked co-star Ethan Slater — who also suddenly ended his own marriage around the same time.
Simon Cowell & Carmen Electra
From 2012 to 2013, everyone was so confused about celebrity couple Simon Cowell and Playboy model Carmen Electra. The pair didn’t last long, however, with reports claiming in that Electra caught Cowell in bed with Lauren Silverman, who he has been with ever since.
Alanis Morissette & Ryan Reynolds
Alanis Morissette and Ryan Reynolds started dating in 2002 after meeting at Drew Barrymore’s birthday party, getting engaged two years later in 2004. However, they ended up calling it quits in 2007, with Morisette writing her iconic album Flavors of Entanglement all about their love story.
Nicole Kidman & Lenny Kravitz
Nicole Kidman’s first serious relatinship after her divorce from Tom Cruise was with Lenny Kravitz in 2003. They dating for around six months and staying great friends after.
Tom Cruise & Cher
We know Cher loves a younger man, and at the beginning of his career in 1985, Tom Cruise dated the Hollywood icon. “He was in the top five [of lovers]. It’s not a long list, just a good list,” Cher revealed in a 2013 episode of Watch What Happens Love. “It could have been a great big romance, because I was crazy for him.”
Zo? Kravitz & Channing Tatum
Zo? Kravitz and Channing Tatum shocked us when they were spotted on dates at the beginning of 2021. What we didn’t know at the time was that Kravitz and Tatum had a whirlwind romance while he was starring her in directorial debut Blink Twice.
After privately dating and getting engaged in 2023, the couple have become much more public and have been happily gushing about their love while promoting their 2024 release.
Macaulay Culkin & Mila Kunis
That 70s Show star Mila Kunis and Macaulay Culkin dated for nine years, starting their romance back in 2002. They kept their relationship incredibly private from the public, ending with a reportedly “horrible” breakup. In an interview with Women’s Health back in 2009, Kunis said, “We grew up together. You find a steady rock in your life, and that’s all you need. We have our ups and downs, but work through them.”
Katharine McPhee & David Foster
Despite both of them being successful singers, Katharine McPhee and David Foster’s age difference is the main thing that shocks people. But even though they’re over 30 years apart, they look so happy since marrying in 2019 and welcoming their son, Rennie, in 2021.
Olivia Wilde & Harry Styles
Olivia Wilde shocked the world not once, but twice in 2020. First by breaking the news that she and longtime lover Jason Sudekis were splitting up, and then sharing that she’d gotten super serious with singer Harry Styles throughout 2021.
After a very high-profile and drama-filled romance, the couple called it quits in 2022.
Zach Braff & Florence Pugh
People had plenty of things to say back in 2019 when Florence Pugh and Scrubs alum Zach Braff started dating. Many thought their 20-year-plus age difference was a red flag, but the couple rose above it all, continuing their romance happily until their 2022 split.
Jessica Biel & Chris Evans
Back in 2001, before Chris Evans became Captain America and Jessica Biel met Justin Timberlake, these two dated for around five years.
John Mulaney & Olivia Munn
One of the biggest scandals of 2021 was when news broke that not only was comedian John Mulaney divorcing his longtime wife, he was also expecting a baby with actress Olivia Munn. This relationship completely came out of nowhere but they’ve gone from strength to strength welcoming their son Malcom in 2021, and tying the knot in 2024.
Elon Musk & Talulah Riley
If you’re most of the population, you didn’t realize that Pride and Prejudice star Talulah Riley married Elon Musk. Not only that, but they got married twice. They started dating in 2008, got married in 2010, and divorced two years later. But then they remarried in 2013 and got divorced in 2016. What a whirlwind.
Shailene Woodley & Aaron Rodgers
Another 2021 couple that threw us for a loop was Shailene Woodley and quarterback for the Green Bay Packers Aaron Rodgers, who announced their surprise engagement that year. However, a year later the pair quietly split.
Fisher Stevens & Michelle Pfeiffer
While everyone in the early 1990s was confused about Michelle Pfeiffer and Fisher Stevens hooking up, they were even more confused about Stevens cheating on her. Like, really?!
Tom Hiddleston & Taylor Swift
While Taylor Swift has dated some unexpected heartthrobs, no one expected her to travel into the MCU for a little romantic detour with Tom Hiddleston. Despite only dating for a few months in 2016, everyone was just confused on whether or not they shipped them together.
Leighton Meester & Adam Brody
Despite being early 2000s royalty, who would’ve bet that not only did Adam Brody and Leighton Meester marry, but also have children together? They married in 2014 and have two children together: daughter Arlo Day, born in 2015, and a son born in 2018 whose name we don’t know yet.
Seth MacFarlane & Emilia Clarke
Get ready, because no one remembers this romance: Family Guy creator Seth MacFarlane and Emilia Clarke. Yup, it happened and it happened for around a year from 2012 to 2013. They split due to long-distance and we’re still wondering how these two even ended up together in the first place.
Renée Zellweger & Ant Anstead
Renée Zellweger and reality star Ant Anstead made headlines when they announced that they were officially dating. Since early 2021, we’ve loved every update from the lovebirds and while we were quite confused at first, they make a perfect couple.
Any Relationship With Pete Davidson
This list would be way too long if we put down every one of Pete Davidson’s relationships — because let’s face it, they’re all kind of shocking. From Kate Beckinsale to now Kim Kardashian, Davidson has no shortage of shock value with his romances with stunning, slightly older women.
Elon Musk & Grimes
Tesla CEO Elon Musk really likes to confuse people with his romances — and his romance with singer Grimes did just that.
They started their surprising relationship in 2018. Their first son, X ? A-Xii, was born in May 2020, and they welcomed their daughter, Exa Dark Sider?l, via surrogate in December 2021 and it’s uncertain when their third child, son Techno Mechanicus, was born. Grimes confirmed their split in 2022.
Jennifer Lopez & Ben Affleck 2.0
None of us expected to be back in the early 2000s again, but Jennifer Lopez and Ben Affleck decided it was 2002 again and got back together in 2021.
Bennifer 2.0 was something we always wanted but never thought we’d get but sadly it wasn’t meant to last. After tying the knot in 2022, the couple split again in 2024.
Taika Waititi & Rita Ora
Where were you when you found out Marvel director Taika Waititi and singer Rita Ora got together? Because we’re still confused about how these two ended up together!
They started dating in 2021 and tied the knot in 2023 after Ora popped the question to Waititi. Talk about taking charge!
Kat Dennings & Andrew W. K.
WandaVision star Kat Dennings and the self-proclaimed “God of Partying” Andrew W.K. are the alt-couple we didn’t know we needed. Their engagement announcement via Instagram came as a total shock and we’re still playing catch up with this relationship. The couple started secretly dating in 2021 and tied the knot in 2023.
Machine Gun Kelly & Megan Fox
Not only was Megan Fox and Machine Gun Kelly’s relationship super shocking, but their double dates with Kourtney Kardashian and Travis Barker are nothing short of chaotic. While their red carpet fashion always wows, their relationship is a lot: between controversial interviews to blood vial necklaces.
Gwen Stefani & Blake Shelton
We suspected sparks were flying on The Voice set, but no one expected superstars Gwen Stefani and Blake Shelton to tie the knot in the summer of 2021. Their wedding was a sight to see, and we’re still scratching our heads over how date night goes in their house between this former ska princess and her country beau.
Kourtney Kardashian & Travis Barker
If you told us that Kourtney Kardashian was going to get engaged to the drummer from Blink 182, we’d be convinced you were talking about fanfiction. But no, 2021 was been all about Kardashian and Travis Barker and whether you love them or hate them, they’re here to stay — and post a lot of PDA.
The duo married in 2022 and welcomed their son, Rocky Thirteen, in 2023.
Rashida Jones & Mark Ronson
Rashida Jones and Mark Ronson started dating back in 2002, falling in love almost instantly and getting engaged the following year. We know, why does no one mention this?! However, they broke up in 2004, but have remained good friends since!
Ryan Reynolds & Scarlett Johansson
Ryan Reynolds and Scarlett Johansson got together back in 2007, instantly becoming a confusing but perfect A-list couple to take over Hollywood. Within a year, the two got engaged and ended up marrying later that year, in Sept 2008 at Vancouver Island. Sadly, their marriage didn’t last long, and their divorce was finalized in July 2011.
Bill Hader & Anna Kendrick
Apparently, Bill Hader and Anna Kendrick were been dating for more than a year before anyone found out!
In 2022, People broke the news that the two have been “quietly” dating, and they are reportedly very happy. “They are both very private people, and with the pandemic it was easy to keep it quiet,” a source told the outlet. Hader and Kendrick previously worked together on the 2019 holiday movie Noelle.
However, while we loved this surprise duo, they called it quits in 2022.
Eric Andre & Emily Ratajkowski
Emily Ratajkowski’s relationship with Eric André was pretty steamy but very short-lived. However, we’re still reeling from it and still thinking about the comedian NSFW Valentine’s Day 2023 snapshots of him and the model that will have you blushing.
Anna Wintour & Bill Nighy
After years of rumors, Anna Wintour and Bill Nighy finally confirmed their relationship at the 2023 Met Gala — and truly, no one saw this couple coming. The pair have known each other for over a decade, and since 2020, have been seen many times together. Truly, this is a power couple we didn’t know would happen.
Nighy has reportedly denied the relationship, saying the two have simply been “great friends for two decades” however, the two continue to spark romance rumors!
Bill Murray & Kelis
Cue the “Mlikshake” jokes! Bill Murray reportedly dated “Milkshake” singer Kelis back in 2023, according to the US Sun, but their romance was short-lived.
The Ghostbusters alum was been spotted at several of Kelis’ shows, and sources said the two were “getting close for a while.”
Kelis lost her second husband Mike Mora to cancer in 2022, and the insider said that’s how they bonded: “they’ve also both shared relatively recent bereavements and have that common bond between them…Whatever it is that has brought them together, and however unlikely it seems, they are both single and are having fun despite the fairly big age gap.”
