Unlikely Celebrity Couples Over the Years

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Unlikely Celebrity Couples Over the Years

They dated?! Some celebrity romances don't always make sense to the untrained eye, but they have kept people interested in their relationship. Florence Pugh and Zach Braff, who were first linked in April 2019, made headlines over their 21-year age difference. After receiving an overwhelming amount of hate on a birthday post for Braff, the Little Women star took to social media to call out the rude comments. "I've been wrestling with the idea for the past few days about whether I should do this video and then finally last night I thought, for my own peace of mind, I should," she started to say in a lengthy Instagram video in April 2020. The Black Widow star noted that "within about eight minutes" of her posting for the Scrubs alum's special day, the comments were filled with hateful messages about their relationship, which made her want to remind her fans that "being hateful is not trendy." "I'm 24 years old. I have been working since I was 17 years old. I have been earning money since I was 17 years old. I became an adult when I was 18 years old and I started paying taxes when I was 18 years old," she continued. "I do not need you to tell me who I should and should not love, and I would never in my life ever, ever tell someone who they can and cannot love. It is not your place. And really it has nothing to do with you ... The abuse that you throw at him is abuse that you throw at me." [jwplayer 2kcvuNSx-zhNYySv2] Later that year, Braff opened up about how he felt seeing his girlfriend defend their relationship so publicly. “She literally sat down, hit record on her phone and said that,” he detailed during an interview with MR PORTER’s digital magazine, The Journal in November 2020. “I thought: how could I possibly follow anything as intelligent and articulate as that? So, I chose not to.” Megan Fox is also no stranger to unkind comments when it comes to her romance with Machine Gun Kelly. "There's so much judgment," the New Girl alum told InStyle in July 2020. "You want to talk about patriarchy? The fact that he's four years younger than me, and people want to act like I'm dating a younger man. He's 31, and I'm 35. Granted, he's lived like he's 19 his whole life, but he isn't 19. No one would blink twice if George Clooney was dating someone four years younger." Fox, who started dating the musician in May 2020, called out the double standards that exist for women in Hollywood. "Four years? Go f--k yourself. We would have been in high school together. That's so ridiculous that women are treated that way," she added at the time. Scroll down for more unlikely couples whose romances fascinated us over the years: [podcast_block]

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Zach Braff and Florence Pugh

The Scrubs alum and the Little Women star started dating in April 2019. When an Instagram user pointed out the couple’s 21-year age difference that December, writing, “@zachbraff you’re 44 years old,” Pugh clapped back, “And yet he got it.” Braff and Pugh quarantined together in Los Angeles amid the COVID-19 pandemic. After months of speculation about their relationship status, the Don't Worry Darling actress confirmed in August 2022 that she and Braff had split. 

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Megan Fox and Machine Gun Kelly

The Transformers star met the "Bad Things" rapper in 2020 while filming the crime thriller Midnight in the Switchgrass. A source told Us in May 2020 that the pair are "officially dating" following Fox's split from her husband, Brian Austin Green. "They're enjoying spending more and more time together and have a strong connection," the insider said at the time.

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Russell Brand and Katy Perry

The comedian met the "Teenage Dream" singer in 2009 when she filmed a cameo for his film Get Him to the Greek. The pair began dating in September of that year after reuniting at the 2009 MTV Video Music Awards. Three months later, Brand proposed while they were on vacation in India. They tied the knot in the same country in October 2010. Brand filed for divorce in December 2011 after 14 months of marriage.

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Flavor Flav and Brigitte Nielsen

The former Public Enemy member began an unexpected romance with the actress in 2004 after they met on the VH1 reality series The Surreal Life. The duo went on to star in their own VH1 series, Strange Love, but they called it quits on their relationship one year later.

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Kate Beckinsale and Pete Davidson

The Underworld actress got flirty with the Saturday Night Live comedian despite their 20-year age gap in January. "Kate and Pete were flirting at the InStyle party and she was following him around a bit and waiting for him,” an eyewitness told Us Weekly at the time. “People approached her and she didn’t want to talk to anyone else.” They were spotted holding hands in L.A. shortly after, with an insider revealing to Us in February, “She likes the fact that he’s younger than her.”

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Channing Tatum and Jessie J

Us exclusively revealed in October 2018 that the actor is dating the British singer following his split from Jenna Dewan. "It’s new, casual and they’re having fun together," a source explained. Tatum and Dewan — who share daughter Everly — announced their separation six months earlier after nine years of marriage. 

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Chris Pratt and Katherine Schwarzenegger

The Guardians of the Galaxy actor and the blogger were first spotted together in June 2018, nearly a year after his split from wife Anna Faris. “They’re dating. It’s new,” a source told Us exclusively. “Her mom [Maria Shriver] set them up because they’re both active in the church. Her family really likes him. They’re really into each other.” Pratt and Schwarzenegger (whose dad is Arnold Schwarzenegger) continued to step out together in the months that followed, including when they went to the Round Pond Estate winery in Napa, California, that September.

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Ariana Grande and Pete Davidson

The “No Tears Left to Cry” singer began dating the comedian in May 2018 just weeks after her split from Mac Miller. Davidson was also recently single following his breakup with ex Cazzie David, and the two quickly started sharing their affection for one another on social media. Us Weekly broke the news in June 2018 that the two were engaged after multiple sources confirmed their happy news to Us. “They are both constantly making each other laugh,” one source said at the time.

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Kat Dennings and Josh Groban

When the hot (and unexpected) new couple stepped onto the red carpet together in October 2014, many were surprised by the pairing. Singer Groban, who previously dated Mad Men actress January Jones, told Entertainment Tonight, “I do have such a lovely date tonight,” calling the 2 Broke Girls star his girlfriend.

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Julie Bowen and David Spade

Claire Dunphy and Dennis Finch?! Back in 2002 Modern Family’s Julie Bowen and David Spade dated for about a year. Now she’s happily married with three kids, both on-screen and off.

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Sandra Bullock and Jesse James

After relationships with actors Tate Donovan, Matthew McConaughey, and Ryan Gosling, Sandra Bullock pulled a wild card when she married famed motorcycle builder Jesse James in 2005. The couple attended public events together for years, including the 2010 Oscars when Bullock took home the Best Actress award for her role in The Blind Side. Shortly after, news of James’ infidelity came out and the couple divorced, leaving Bullock to raise her adopted son Louis as a single parent.

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Christina Hendricks and Geoffrey Arend

Christina Hendricks’ curvy figure has made her into a sex symbol ever since her role as Joan Harris on Mad Men, which her actor husband (since 2009) Geoffrey Arend, thinks is funny. "It's incredibly flattering and surprising, and I didn't think for a second when I started Mad Men that people would talk about me as being sexy or a pinup," she told Cosmopolitan UK in 2012. "My husband has a good laugh about it, of course."

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Amber Tamblyn and David Cross

Holy age difference, Batman! Despite being 19 years his junior, The Sisterhood of the Traveling Pants star Amber Tamblyn tied the knot with comedian David Cross in 2012 while wearing a marigold yellow dress. “There’s nothing really traditional about me,” she told Us Weekly in 2012.

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Lady Gaga and Taylor Kinney

Mother Monster found her mate! Lady Gaga is known for her over-the-top costumes and wild on-stage antics, but she found a relatively normal match in hunky Chicago Fire star Taylor Kinney. Despite being a powerful woman, Gaga said she’s submissive in her relationship. "He's totally in charge. I mean, when I am home, I am like, shoes are off, I'm making him dinner. He has a job, too, and he is really busy!" she told SiriusXM’s The Morning Mash Up in March 2014.

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Cameron Diaz and Benji Madden

Us confirmed the actress and Good Charlotte rocker were dating in May 2014, and the two stepped out several weeks later holding hands in NYC. The couple's mutual connection? Nicole Richie. "She's happy to have someone to do boyfriend/girlfriend stuff with," a source told Us. "They're both diving straight in."

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Chelsea Handler and 50 Cent

"He's a sweetheart and he's so cute," Handler told Oprah Winfrey of her rapper ex, whom she was reluctant to cozy up to. "It wasn't the most serious relationship. He came on my show [in 2010] and he sent me flowers. And I was like, 'I'm not gonna date somebody whose name is a number.'"

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Tom Cruise and Cher

"It was pretty hot and heavy for a little minute. He's a great guy," Cher has said of her early '80s ex, ranked by the "Woman's World" singer as one of her top five lovers. "The person that I knew was a great and lovable guy."

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Justin Timberlake and Fergie

Long before Timberlake married Jessica Biel and Fergie welcomed her first child with Josh Duhamel, the musicians dated one another while Fergie's girl group Wild Orchid toured with 'N Sync. "He was 16 and I was 23," Fergie told Australia's Courier Mail. "It was before he got real heavy with Britney [Spears]."

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Brooke Shields and Michael Jackson

In 1984, the actress was the late singer's date to the Grammy Awards. He wrote about their romantic involvement in his 1988 autobiography, but Shields claimed they were just friends. "We grew up together," she told the AP. "He trusts me."

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Mary-Kate Olsen and Olivier Sarkozy

Though the former Full House actress is 17 years his junior, she said yes to the once-wed millionaire Sarkozy in February 2014. "He tried about a year ago, and she wasn't ready," an insider told Us at the time. "She didn't need to be wined and dined. She wanted to make sure he would be good to her."

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LeAnn Rimes and Tiger Woods

Currently linked to skier Lindsey Vonn, Woods previously romanced the blonde country star. "They hooked up and everything," a source told Us of the golfer and Rimes, now married to Eddie Cibrian. "Tiger was really into her. He likes those blondes!" Rimes' father is said to have protested their relationship because Woods was seven years her senior.

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Hugh Hefner and Crystal Harris

Two years and one broken engagement later, Playboy founder Hefner and his 60-years-younger girlfriend made it official in a New Year's Eve wedding ceremony at the Playboy mansion in 2012. "When the wedding didn't work out the first time, it was because of me. I needed to explore out there and take the time away [from Hef and the Mansion]," Harris told Us. "The time away really helped make me realize that where I'm meant to be is here with Hef."

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Brandi Glanville and Gerard Butler

"It was a one-afternooner, but it was fun," Butler told Howard Stern of his fling with the Real Housewives of Beverly Hills star, whose name the actor admitted he forgot. "She is wild." Glanville's take on Butler as a lover? She rated him an 11 out of 10.

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Olivia Wilde and Jason Sudeikis

"I thought, 'He won't be interested in me; I'm not a contender,'" Wilde told Marie Claire of her now-fiance, whom she began dating after meeting at the 2011 SNL finale. "He was so cool, so funny — I was such a fan of his and had always fancied his speed and his intelligence. He's a brilliant actor with a brain like lightning...I thought, 'I'm not beautiful enough or his type.'" The couple welcomed son Otis in April 2014.

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AnnaLynne McCord and Dominic Purcell

"What I like about an older man is that they tend to be your rock," the actress tells Us of her lasting bond with husband Purcell. "Whenever I have my crazy [moments], like, 'Ah, this is never going to work out!' Then he's there. "I need a guy who's confident and is secure in himself, because we're always apart."

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Chad Kroeger and Avril Lavigne

Kroeger was so sure the "Complicated" singer was The One that he proposed to her with a 14-carat diamond — without even introducing her to his parents. "My mom is a huge fan of Avril's, so putting her on the speaker phone and telling her the news was hilarious and equally embarrassing." The couple tied the knot in July 2013 during a weekend of partying in the south of France. Sadly, Us Weekly broke the news that the couple was heading for a split one year later.

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Carole Radziwill and George Clooney

During a 2012 episode of The Real Housewives of New York City, Radziwill's costar, Sonja Morgan, spilled the beans about her fling with Clooney. As Radziwill showed off her sexy bod in a tiny bikini on the beach, an impressed Morgan quipped: "Look at the ass on Carole . . . No wonder Clooney did her for a year."