Love Finds a Way: Here Are All the Most Unexpected Celebrity Couples of 2021

For every famous duo that seems inevitable, there's a pairing that leaves you wondering how that happened. Here are the celebrity couples who made us go "Wait, what? Really?!" in 2021.

By Natalie Finn Dec 25, 2021 11:00 AMTags
Unexpected Celebrity Couples of 2021Melissa Herwitt / E! Illustration

When you're taking a break from your real-world concerns and living that online life, what's more fun than a little celebrity romance to root for? Or relentlessly analyze? Or resent? (We're not judging.)

In fact, following the love lives of the rich and famous can be quite heartening, serving to remind us that everyone has their ups and downs, you never know when you might get hit with the thunderbolt, that there's still love to be had after a painful breakup, or that Cabo will always be there for us.

But while it's easy to applaud a pairing that's as logical as peanut butter and jelly, or Tom Holland and Zendaya, there's also nothing like a couple coming out of nowhere to put some extra wind in the sails of our shipping game. And 2021 had more than its fair share of high-profile dating activity that had us wondering when and where and how, exactly, certain twosomes found each other.

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Best TV Couples of 2021

Some couples quickly proved to be more suited than a first glance might indicate, eventually joining the ranks of the inevitable, while others remain flow-chart-necessitating mysteries. Some will be ringing in the new year betrothed, and some are already exes. And someone showed up on this list twice!

Watch: Celebrity Couples We Hope NEVER Split

But what the most unexpected couples of the year ultimately prove, it's that this sort of chemistry can't be explained with simple equations: 

Ben Affleck and Jennifer Lopez

And here we thought we'd be recycling those 2003 red carpet photos forever.

If the recoupling of the original Bennifer, 16 years after they broke up in a haze of box office poison, isn't enough proof that no one knows what the future holds and anything is possible, then we don't know what to tell you.

Maybe for those who never stopped believing they were each other's lobster, it was just a matter of time. But considering Lopez began 2021 engaged to Alex Rodriguez and Affleck had been dating his Deep Water co-star Ana de Armas for months, no one actually had this on the bingo card they were required to turn in to the Fates when the clock struck midnight on Jan. 1.

Ana de Armas and Paul Boukadakis

Since Affleck's January ended with a cardboard cutout of de Armas winding up in a trash barrel outside his house, we were happy to see the Knives Out star swiping right on the vice president of Tinder, Paul Boukadakis.

They were reportedly introduced by mutual friends in June and a source told E! News in December that they're "very serious" about each other.

And one potentially awkward reunion has already been avoided: Originally scheduled to come out Jan. 14, 2022, Disney has pulled the psychosexual thriller Deep Water, starring Affleck and de Armas as a married couple who start seeing other people to stave off divorce (what could go wrong?!), from its release calendar.

Olivia Wilde and Harry Styles

Stop your crying, it's a sign of the times!

Technically they started dating last year after hitting it off on the set of Wilde's latest directorial effort, Don't Worry Darling, starring Styles and Florence Pugh, but they didn't go public as an item until January.

At first glance they may seem like an odd couple (Wilde has two children with ex Jason Sudeikis and Styles has inspired at least three Taylor Swift songs), but obviously they're mutual fans of each other's artistry. And, as the saying goes, if you are hot and free, so it must be.

"It's obviously really tempting to correct a false narrative," Wilde told Vogue for its January 2022 issue when the topic of her relationship was broached. "But I think what you realize is that when you're really happy, it doesn't matter what strangers think about you. All that matters to you is what's real, and what you love, and who you love."

Aaron Rodgers and Shailene Woodley

The Green Bay Packers quarterback and the actress who had never seen a football game before they met kicked off the year at first and goal, with Rodgers revealing Feb. 6 that he had a fiancée, hot on the heels of E! News confirming that he and Woodley were a couple.

"It's a quick engagement, but for those that know them, it didn't come as a surprise," a source explained.

But reader, will she marry him?

Let's just say, despite their delightful-looking trips to Hawaii and the Kentucky Derby with pals Miles Teller and his wife Keleigh Sperry, it's been an intense year. Woodley found herself coming to Rodgers' defense amid a summer of uncertainty about whether he'd return to his longtime team, and again in November when he was branded a liar by some after he tested positive for COVID-19 and it turned out he was unvaccinated—having told reporters in August that he was "immunized" against the virus.

Still, Rodgers' Packers have already clinched their third straight NFC North title, so he's got plenty of spring in his step, and we'll see what happens off the field in 2022.

Travis Barker and Kourtney Kardashian

It became apparent in January that the Blink-182 drummer and the Poosh founder had taken their years-long friendship to the next level. And before we knew it, they had also become the most explicitly into each other couple of the year, giving their pals Megan Fox and Machine Gun Kelly a run for their money in the PDA department.

Perhaps Kardashian, never known as the most in-love-with-love member of her family, was simply making up for lost time, having spent a lot of years trying to make it work with Scott Disick, the father of her three kids. And then, while she did date, she didn't seem particularly interested in settling down, let alone getting married.

But maybe she just finally found her other half, and vice versa. Barker, a father of two who's also had enough domestic drama to last a lifetime, even started traveling on airplanes again—for the first time since surviving a fatal crash in 2008—so they could cross oceans together. By the time he popped the question in October after 10 months so steamy you needed a squeegee to look at their Insta accounts, no one was surprised. 

They may have started the year in the "out of nowhere" file, but they're ending it under "perfect fit."

Pheobe Dynevor and Pete Davidson

Despite his steady flow of self-deprecation regarding his desirability, Davidson never seems to be without a gorgeous woman by his side for long.

And since the Saturday Night Live star spent a few months of this year getting to know the British Bridgerton actress, going all the way to her native England to hang out,  we can now confirm that his appeal is international.

Kim Kardashian and Pete Davidson

Sure, why not? Kim was going to start dating again eventually after filing for divorce from Kanye "Ye" West in February, so why shouldn't she let her hair down with Pete "King of Staten Island" Davidson? All signs point to the comedian being a blast to ride a roller coaster with, and the mother of four—who also finally passed the exam known as the baby bar in her quest to become a practicing attorney in California—deserves to enjoy herself.

"They are really happy and seeing where it goes," a source told E! News in November.

John Mulaney and Olivia Munn

The Violet star first met the comedian at Seth Meyers' wedding in 2013 and considered herself a fan. But it wasn't until this year, which started with Mulaney in rehab and still married to his wife Anna Marie Tendler, that they became both a couple and parents, welcoming their first child on Nov. 24.

"She got to date me right out of recovery, which is what they call a reverse catch," Mulaney, who filed for divorce from Tendler in July, quipped during a Sept. 7 appearance on Late Night With Seth Meyers. "I got into this relationship that's been really beautiful with someone incredible who has like, dealt with the non-coked up Bambi version of me, and that's been very incredible and she's kind of held my hand through that hell. And we are having a baby, together."

Acknowledging how it all kinda looked to outsiders, Munn told the Los Angeles Times in November, "It's definitely not foreign for me to have people speculate incorrectly about things and to have rumors run rampant in one way."

Moreover, she added, "They think they know our relationship so well. When in reality, they don't. There's no way anyone could know what any of his relationships were or what our relationship is."

Channing Tatum and Zoë Kravitz

Well, if we were going based on sheer aesthetics and what might happen when you're making a movie called Pussy Island, then sure, we would've seen these two coming a mile away. 

But admittedly, it was a surprise, not least because the early word in January was that they were not dating as Kravitz started proceedings to divorce her husband of 18 months, Karl Glusman. By August, though, the Big Little Lies star and Tatum, who's father to daughter Everly with ex-wife Jenna Dewan, were inching out into the open. The next month, they stunned (albeit separately) on the Met Gala red carpet and left the ball together.

Whether they keep this going or not, Kravitz will forever be responsible for getting Tatum to excise the Crocs from his wardrobe, so she's already made his forever-mark on his life.

Renée Zellweger and Ant Anstead

It does seem that the two-time Oscar winner from Texas would appreciate a handy fellow, and Anstead—whom she met taping the first episode of his Discovery+ show Celebrity IOU: Joy Ride, on which he helps stars restore the ideal vehicles for deserving people in their lives—certainly fits that bill.

Though a fixture of gearhead TV in his native Britain for years, Anstead became more known on these shores when he wed Christina Haack of Flip or Flop fame, the second marriage for both of them. Each parents of two already, they welcomed son Hudson in September 2019 before separating a year later.

He started dating Zellweger in June, still smitten even after finding out she wasn't actually British.

Adele and Rich Paul

Nowadays, our celebrity sightings at Los Angeles sporting events aren't complete without a shot of Adele sitting courtside or in a VIP box. She met Paul a few years back, but she and LeBron James' agent—who's also a good friend of her pal Drakejust started seeing each other in May.

"I didn't really tell many of my friends at the beginning because I wanted to keep it to myself," Adele told Rolling Stone this past fall of her low-key romance. "None of them believed it!"

The 30 artist's divorce from Simon Konecki, the father of her son Angelo, was finalized in January, two years after they split up.

Meghan King and Cuffe Biden Owens

The former Real Housewives of Orange County star embarked on her third marriage by wedding President Joe Biden's nephew on Oct. 11, less than a month after revealing they were a couple. (Cuffe's mom is the commander-in-chief's sister, Valerie Biden.)

Ex-husband Jim Edmonds, with whom King shares three kids, told the Daily Mail after the surprise nuptials that she had called him to let her know her plans ahead of time, but, "It was the first I heard anything about it. I thought it was a joke—they'd been dating for about four weeks!"

It wasn't a joke—nor was King's apparent acknowledgment on Dec. 27 that the whirlwind romance didn't work out after all, confirming suspicions raised when her holiday-themed posts on social media didn't include her new husband. On Instagram Story she called the situation "profoundly devastating," adding, "This is obviously not what I imagined when I made my vows—and I'm shocked and saddened by the way things turned out."

Lindsay Lohan and Bader Shammas

Lohan's engaged! To this guy! Who's an executive at Credit Suisse in Dubai, where she's been living, but we'd never heard of him throughout their three years of dating before she flashed her ring! Surprise!

"My love. My life. My family. My future," the actress shared on Instagram.

Katie Thurston and John Hersey

Did you think Thurston would be revisiting a romance with Hersey? Barely a month after she and Blake Moynes revealed they'd ended their engagement?!

If "revisit" is even the right word, since Thurston denied Hersey a rose after week two of her journey on The Bachelorette.

"A lot has changed in the last four weeks," a source told E! News in November of the recent coupling. "And it's been wild but exciting for those closest to them to witness."

So let this be a lesson: No matter where you're at on Jan. 1, you could easily be in an entirely different place—emotionally, spiritually, professionally and geographically—by Dec. 31.