By Jessica Wedemeyer
8:14am PST, Dec 27, 2021
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In mid-May — just a few days after the news broke that John Mulaney and his wife of six years, Anna Marie Tendler, were throwing in the towel — People magazine reported that the funnyman had already moved on with Olivia Munn. But that wasn't the only shock: It soon became clear that the duo were expecting their first child together. In mid-December, it emerged that Olivia quietly gave birth the day before Thanksgiving, indicating she and John have been a couple for longer than previously known (John had told late night host Seth Meyers he met and started dating Olivia "in the spring"). There's a reason why the baby news was also particularly surprising: The stand-up comedian completed multiple rehabs stints for alcohol and cocaine addiction in the previous year and had also said just two years earlier that he didn't want kids.
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Olivia Wilde and Harry Styles really set the bar for 2021 when they revealed in early January that they were an item. After photos of the duo holding hands at a wedding in Montecito, California, hit the Internet, multiple media outlets reported that the pair fell for each other on the set of "Don't Worry Darling" in late 2020. (The 37-year-old actress-filmmaker directed the 27-year-old former One Direction singer in the upcoming thriller.) The new relationship raised questions about the timeline of Olivia's 2020 split from former longterm partner Jason Sudeikis. (In November 2020, reports indicated that they'd split early that year, while others claimed the breakup was more recent. In a Vogue cover story that hit the internet in December 2021, Olivia said, "It's obviously really tempting to correct a false narrative. 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.") There were also conflicting reports about whether or not the "Saturday Night Live" alum was aware his ex had moved on so soon. Some sources described Jason as "absolutely heartbroken" and "blindsided" by Olivia's relationship with Harry, noting that he had hopes for a reconciliation. He wasn't the only one blindsided by their relationship, which grew increasingly serious over the course of the year.
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It was easily the most shocking celebrity romance of the year — maybe even of the decade! Kim Kardashian West started spending time with Pete Davidson after they bonded when she hosted the Oct. 9 episode of "Saturday Night Live" amid her divorce from Kanye West, and by mid-November, they were "officially dating." Later that month, a People magazine source shed some light on the connection between the mother of four and the funnyman, who's 13 years her junior: "He's exactly what Kim needed after her divorce — someone to make her laugh and just have a fun time with," the source said. "The end of her marriage was a very dark time for her and Pete has been the best antidote." Good for her!
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Before he made waves by dating Kim Kardashian West, Pete Davidson romanced "Bridgerton" breakout star Phoebe Dynevor. They were first linked in March — though, at the time, the romance rumor seemed as fictional as the Netflix show that made her a star. Not so! The pair made their public debut at Wimbledon in July but called it quits the following month. At this point, nothing should really surprise us anymore when it comes to the "Saturday Night Live" star's romantic conquests — he's dated some of the most beautiful and talented women in Hollywood over the course of the past few years. His long list of ex-lovers includes Ariana Grande, Kate Beckinsale, Kaia Gerber and Margaret Qualley. There were also questions about the nature of his relationship with newly single "Meet Cute" co-star Kaley Cuoco in early September.
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Meghan King practically broke the Internet in late September when she took to Instagram to reveal that she had a new boyfriend: President Joe Biden's nephew, Cuffe Biden Owens. That was just the beginning of the surprises… Just two weeks later, the former "The Real Housewives of Orange County" star — who's known for airing her dirty laundry and publicly feuding with her first husband, Jim Edmonds — and the handsome lawyer (they're pictured here with her brother and sister) tied the knot in front of guests including the president and first lady Jill Biden. Us Weekly later reported that the newlyweds knew each other for just three weeks before they became husband and wife. Unsurprisingly, it wasn't meant to be: On Christmas Eve, Page Six reported that they'd called it quits just two months after exchanging vows.
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It makes so much sense now, but when the news first broke in January that Kourtney Kardashian and longtime pal Travis Barker had finally taken their relationship to the next level, people were stunned! After all, she's a glamorous reality TV star who predominantly dated younger men following her final split from Scott Disick in 2015 after nearly a decade of off-and-on coupledom. And he's a tattooed rock star who hand't been in a serious relationship for years. Plus, it seemed inevitable that she and Scott would eventually reconcile — even Scott thought as much! Still, the love between Kourtney and Travis was the real deal: The duo, who quickly blended their families, got engaged in October after less than a year of coupledom.
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"Ted Lasso" fans were delighted when Jason Sudeikis started spending time with English actress Keeley Hazell — who portrays Bex on the hit Apple TV+ series — in early 2021 following his painful 2020 split from former long-term partner Olivia Wilde. As their romance blossomed over the course of the year, fans were even more thrilled to learn that the funnyman and the former glamour model were long-term pals before things between them turned romantic — and that she even reportedly served as the inspiration for Juno Temple's "Ted Lasso" alter ego! It was a lovely surprise for everyone rooting for Jason, who was reportedly blindsided and devastated when Olivia suddenly moved on with Harry Styles earlier this year.
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Who could've guessed when Ant Anstead and Christina Haack suddenly called it quits in September 2020 that he would move on with an Oscar-winning actress? Well, that's exactly what happened! The English former "Wheeler Dealers" host started dating one of our all-time favorite leading ladies, Renee Zellweger, in mid-2021 and by the end of the year, they were reportedly living together.
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While there's certainly nothing shocking about two of Hollywood's hottest stars falling for each other, we were still surprised — pleasantly surprised! — when the friendship between Channing Tatum and Zoe Kravitz turned into something more after she cast him in her feature film directorial debut following her late-2020 split from her husband of just 18 months, Karl Glusman. The comely couple signaled they were the real deal when they made their relationship Instagram official on Nov. 1.
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A workplace romance no one could've predicted! In late July, Chrishell Stause revealed on Instagram that she and "Selling Sunset" co-star Jason Oppenheim — who co-founded The Oppenheim Group, the high-end real estate brokerage firm at the center of their hit Netflix reality show — were more than friends. Jason later confirmed to People magazine that he and the former soap star "became close friends" before things between them turned romantic earlier in the year. By late December, however, they were through.
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Jana Kramer and Jay Cutler sent shockwaves through Nashville when they started spending time together in September — fresh off her breakup from Mike Caussin and his split from Kristin Cavallari. There's nothing scandalous about two recently single stars sparking up a romance, but there was one major problem with the potential new love connection: Jana and K.Cav had been friends for years! While Jana-friendly sources tried to downplay the friendship, Kristin told Us Weekly herself in August that she and the "One Tree Hill" alum "hang out" because they're "both in Nashville" so they "don't have to do Zooms." Another Us Weekly source, meanwhile, said that Jay only went out with Jana to make his ex jealous. Despite the conflicting reports, one thing was clear: It wasn't a match made in heaven. By early October, Jana and Jay were done.
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In late September, MailOnline reported that Emma Watson was dating Brandon Green — the son of controversial British billionaire Sir Philip Green, who's been accused of everything from sexual harassment and racism to tax evasion and workers' rights violations. Fans were shocked that the clean-cut former child star, who's known for her work as a humanitarian and activist, would choose to spend time with someone with such a controversial clan. Also shocking? It was the first indication that Emma and her boyfriend of two years, Leo Robinton, had called it quits after sparking engagement rumors earlier in the year.
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In late February, Lucy Hale and Skeet Ulrich were snapped smooching during lunch in Los Angeles. According to an E! News source, the 51-year-old former teen heartthrob and the 32-year-old "Pretty Little Liars" alum "were set up through mutual friends" and were "both really into each other." It wasn't meant to be, though: By late April, they were through.
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In early September, multiple media outlets reported that clean-cut former child star Soleil Moon Frye was dating heavily tattooed Crazy Town frontman Seth "Shifty Shellshock" Binzer. The former child star and the "Butterfly" singer had been friends since eighth grade and finally took their relationship to the next level in early 2021 following her late-2020 split from Jason Goldberg after more than two decades of marriage.
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In November, Casey Affleck revealed he'd started dating a woman who's literally half his age: Caylee Cowan. Not long after they were snapped smooching in Los Angeles, the 46-year-old Oscar winner made their relationship Instagram official. The 23-year-old actress was born in 1998 — two years before Casey started dating his ex-wife, Summer Phoenix, from whom he split in 2015 after nearly a decade of marriage and two kids together. Adding to the shock factor, Casey's public displays of affection for Caylee were the first indication that he and long-term girlfriend Floriana Lima — to whom he was first linked in late 2016 — had called it quits.
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The world was stunned when Bella Hadid casually unveiled her boyfriend, art director Marc Kalman, on Instagram in early July. Why was the reveal so major? Just a few days later, Page Six reported that the pair had actually been secretly dating for A FULL YEAR! How did she manage to keep her relationship a secret for so long? We'll never know!
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She's a British pop star and he's an Oscar-winning writer who's also helmed several major Marvel movies, so we took it with a grain of salt when The Sun reported in late April that Rita Ora and Taika Waititi were an item. In mid-May, however, they proved the rumors were true by packing on the PDA during a low-key outing in Australia's Bondi Beach. Things have only gotten more serious since then!
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The beauty and the brains! In late April — just days after they first sparked romance rumors — Paulina Porizkova and Aaron Sorkin confirmed they were a couple by posing together on the red carpet at the 2021 Academy Awards. Fans were thrilled — albeit surprised! — to see the supermodel and the Oscar-winning filmmaker together. Sadly, though, it wasn't meant to be: They split just three months later.
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Christina Ricci was full of surprises this year! When the former child star took to Instagram on Aug. 10 to announce that she was pregnant with her second child, she raised questions about the nature of her relationship with hairstylist, makeup artist and photographer Mark Hampton by tagging him in the pregnancy announcement. (It was the first indication she was seeing someone new in the wake of her breakup from her husband of seven years, film producer James Heerdegen, in the summer of 2020.) Just two months later, Christina and Mark tied the knot. They welcomed daughter Cleo in early December.
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We didn't realize she was so rock 'n' roll! In mid-May — just 10 days after Kat Dennings revealed that she and Andrew W.K. were an item — the "WandaVision" actress took to Instagram to announce that they were engaged. The following month, the fast-moving couple sparked rumors that they'd quietly tied the knot. What a whirlwind!
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He's one of the biggest DJs in the world, and she's the third of Meryl Streep's four children. It doesn't necessarily make sense on paper, and yet the romance between Mark Ronson and Grace Gummer is apparently the real deal. The couple took off like wildfire: They were first publicly linked in March, they sparked engagement rumors in May and they tied the knot in August.
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In mid-August, Hollywood "it" girl Margaret Qualley was snapped packing on the PDA with one of our favorite geek-chic musicians, Jack Antonoff, in New York City. The sweet snaps proved rumors from late June claiming that the 26-year-old "Once Upon a Time… In Hollywood" actress and the 37-year-old Bleachers frontman and Taylor Swift producer were, in fact, an item. The romance came as a surprise considering there'd been no prior indication that Jack and former longtime love Carlotta Kohl had called it quits: They attended the 2021 Grammys together in March, and she directed the music video for Bleachers' single "Stop Making This Hurt," which debuted in May 2021.
