Hollywood's Most Surprising Singer-Actor Couples

There were oh-so-many jokes tweeted about Metamucil milkshakes when a rumor made the rounds about Kelis potentially dating "Groundhog Day" actor Bill Murray. And with this being the 2020s, it's easy to accept anything random and odd as being possible — even a weatherman reliving the same day over and over again.

In early June 2023, The U.S. Sun reported that Kelis' milkshake had brought Murray to more than one of her concerts, and the pair even posed for a pic together after a show in London. "They've clearly hit it off," an insider claimed. "They were both seen at the same hotel." Kelis didn't outright bust the rumors that she and the "Ghostbusters" actor were a couple when addressing the topic on Instagram. Many of her followers brought it up in the comments section of a bikini photo, and in response to one remark, Kelis wrote, "Lol yeah maybe for now everyone's dumb and will believe anything but the best part is we are both blessed, rich and happy."

While Kelis pointed out that she and Murray had a lot in common, they still seemed like an unlikely pair — there's their 29-year age difference and the difficulty many people likely have imagining that Murray even knows what "diamonds on my grill" means. But in the entertainment industry, music and acting are two adjacent fields that often overlap, and it's not actually all that unusual to see unusual singer-actor pairings.

Natalie Portman and Devendra Banhart first met when she asked the eccentric folk singer to contribute one of his songs to a charity album, per People. She, in turn, appeared in Banhart's "Carmensita" music video, in which he had her transform from a princess into a cephalopod. In a 2009 interview with Pitchfork, Banhart confessed to falling for Portman while working with her.

Their relationship began and ended in 2008. The following year, Portman met her future husband, Benjamin Millepied. While their time together was brief, Portman and Banhart blessed us with one special moment that we just can't forget: The pair were walking Portman's dog when another random pooch stopped to pee on the "Black Swan" star's feet, per the New York Post.

Banhart has also shared a bit of fun trivia about a connection he has to some of Portman's films. He told Spin that his middle name is Obi, after the older version of the "Star Wars" character. He explained that his mother was pregnant with him while watching the first movie. "Alec Guinness came on, and I started kicking," he said. Luckily, Banhart grew up to be a "Star Wars" fan, but he was not impressed with the prequel series that his ex appeared in. "I don't entirely honor her films. I try to forget that the prequels exist, I really do," Banhart said. "So we just avoided the subject for the sake of my mental state."

Who knew that a Sindar elf and Smurfette would make such a perfect match? Orlando Bloom and Katy Perry welcomed a baby bloom named Daisy Dove to the world in 2020 after four years of on-and-off dating. But long before the "Pirates of the Caribbean" star and the "Harleys in Hawaii" singer celebrated having a bun in the oven, Bloom swashbuckled his way into Perry's heart by plundering one of her burgers.

In a 2019 episode of "American Idol," Perry shared the story of how she got a hankering for some In-and-Out at a 2016 Golden Globes party. Thankfully, security guards will also fetch food for you if you pay them well enough, and Perry soon possessed of a pile of burgers. "All of a sudden I see my (future) boyfriend's hand — he wasn't even sitting at our table — he just swoops in and he grabs it and I was like, 'Hey that's my burger!'" she recalled (via HuffPost). You might say that burger was — the one that got away.

After calling time on their relationship in 2017, Perry and Bloom reconciled the following year. Bloom popped the question on Valentine's Day in 2019 with a ring that had a fittingly floral setting. When Perry dressed up like a burger for a Met Gala afterparty three months later, we wonder if she had to hire extra security to keep her Hamburglar future hubby away.

Before Coldplay frontman Chris Martin began dating "Fifty Shades of Grey" actor Dakota Johnson in 2017, he had already found a ladylove in one thespian, "Shakespeare in Love" star Gwyneth Paltrow. Like Martin's ex-wife, Dakota is also a nepo baby; her mother and father are actors Melanie Griffith and Don Johnson, and Gwyneth's parents are actor Blythe Danner and filmmaker Bruce Paltrow.

Gwyneth welcomed Dakota into her blended family with open arms. People reported that Gwyneth invited Dakota and Martin to celebrate Thanksgiving at her place in 2018, where they were joined by Martin and Gwyneth's children, Apple and Moses, as well as Gwyneth's husband, Brad Falchuk. In a 2020 interview with Harper's Bazaar, Gwyneth said of her ex's girlfriend, "I love her. I can see how it would seem weird because it's sort of unconventional. But I think, in this case, just having passed through it iteratively, I just adore her."

Martin and Dakota are more reticent to talk about their feelings for each other publicly, but during a 2021 Coldplay concert, Martin revealed that the song he was about to sing, "My Universe," is about his significant other. The singer and actor had previously collaborated together on the 2020 music video for "Cry Cry Cry," with Dakota directing her man and his band. "I wrote the story and pitched it to the band like every other director did, and they chose mine — not because they're partial to me at all," she told Marie Claire.

When "Boy Meets World" star Matthew Lawrence met another '90s icon, he certainly didn't make her feel unpretty. Lawrence, who was previously married to "Dancing with the Stars" pro Cheryl Burke, told ET that he and TLC member Rozonda "Chilli" Thomas connected when he wound up on the same flight as her, thanks to a snowstorm that forced him to change his travel plans. "Really it was the flight, talking and then afterwards saying, 'Hey, let's keep in contact.' That's really what made it," he said.

When Lawrence and Chilli made their relationship Instagram official in late December 2022, they surprisingly didn't choose a '90s song for the adorbs video that they filmed together. Instead, they danced to A-ha's '80s hit "Take On Me" while wearing matching festive onesies. "This makes me very happy!!" Lawrence's "Boy Meets World" co-star, Danielle Fishel, wrote in the comments.

Once the cat was out of the bag, Lawrence and Chilli could not stop gushing about how much they adore one another. "I am so happy. Yeah, I don't even know what to do with myself," Chilli told Extra in March 2023. "He's the best." Her bandmate, Tionne "T-Boz" Watkins, confirmed to the outlet that she'd never witnessed Chilli being so happy with someone. That same month, Lawrence told ET that he'd love to start a family with his girlfriend someday. "That's the game plan. That's what we're trying to do," he said.

In her March 2023 appearance on the "Armchair Expert" podcast, Bollywood star and former Miss World winner Priyanka Chopra revealed how her relationship with Nick Jonas began. "He slid into my DMs on Twitter," she said. "... I was in a tumultuous relationship at that time — this is [2016]. We had common friends who didn't want me to be in my relationship and were like, 'Oh, he's single, too.'" Well, not exactly — the Jonas Brothers singer was actually seeing someone, but Chopra's friends assured her it wasn't serious. She also revealed that Nick's brother, Kevin Jonas, was a big fan of her show "Quantico" and was pushing Nick to contact her.

The couple began communicating via text, and Nick eventually decided to shoot his shot publicly by kneeling down before Chopra at Vanity Fair's 2017 Oscars party. "I say, 'You're real. Where have you been all my life?' Like, loud," Nick recalled to Vogue. He begged Chopra to have a drink with him, and she agreed. The following year, he proposed during a trip to Crete.

The couple celebrated their nuptials in India in December 2018, and they welcomed their daughter, Malti, via surrogate in 2022. She was born premature and remained in the NICU for months. "We spent every single day with her on my chest, on my husband's chest," Chopra recalled to British Vogue. Now, Malti is thriving and blessed to be growing up with two talented, loving parents.

Olivia Wilde had cause to worry when her love life threatened to overshadow the second feature film she directed, "Don't Worry Darling." In 2020, Deadline reported that Harry Styles would be replacing Shia LaBeouf in the psychological thriller. Once the "As It Was" hitmaker was onboard, no one could have predicted the saga of cinematic friction and infatuation that would follow.

That November, People reported that Wilde and her fiancé, "Ted Lasso" star Jason Sudeikis, had split months earlier after seven years and two children together. The following January, Page Six published photos of Wilde and Styles holding hands at the wedding of Styles' agent, Jeff Azoff. Rumors soon began swirling that Styles' "DWD" co-star, Florence Pugh, was unhappy about Styles and Wilde falling in love at work. A source alleged to Vulture that Pugh believed the lovebirds spent too much time together away from the set, and her continued irritation culminated in her and Wilde supposedly screaming at each other. Another insider told Page Six Pugh was angry about the relationship because it allegedly began when Wilde and Sudeikis were still together. Wilde vehemently denied this to Vanity Fair, saying, "The complete horses*** idea that I left Jason for Harry is completely inaccurate. Our relationship was over long before I met Harry." Meanwhile, dozens of "DWD" crew members called the on-set drama claims "completely false" in an open letter, per People.

Despite all the alleged drama surrounding it, Wilde and Styles kept their relationship pretty private until it ended in November 2022, two months after "DWD" hit theaters.

"Hole in the Bottle" hitmaker Kelsea Ballerini and "Outer Banks" actor Chase Stokes were both parties in some high-profile relationships before they started dating in 2023. After almost half a decade of marriage, Ballerini and fellow country music artist Morgan Evans called it quits in 2022. As for Stokes, he and his "Outer Banks" co-star, Madelyn Cline, ended their year-long relationship in late 2021.

On the "Call Her Daddy" podcast, Ballerini revealed that she made the first move in her relationship with Stokes, even though she'd never watched his popular Netflix series. She decided to slide into his DMs, saying, "I just swan dove right on in. ... His handle is @hichasestokes, and I said, 'Hi, Chase Stokes.'" Ballerini's move was pretty ballsy, considering that the dating game was totally new to her. "I don't know how it works," she confessed. "I'm like, 'Let's just put ourselves out there — let's just vibe.' And it's been fun." 

Ballerini managed to fetch herself a beau who thinks that she's the cat's meow and the dog's bow wow. After telling ET that he's totally fine with the internet calling him a "golden retriever boyfriend" (which basically just means that he's really sweet and affable), Stokes said of his girlfriend, "Oh my gosh, she seriously is the best human being on planet Earth and she's so d**n talented." So, stepping outside of their respective industries to find love certainly worked out well for the pair.

Before he and Jennifer Aniston first hooked up in 2008, John Mayer had already built the foundation of his reputation as one of Hollywood's most prolific lotharios. At the time, his exes included Jennifer Love Hewitt, Jessica Simpson, and Minka Kelly. Aniston told Vogue that her first encounter with Mayer happened at an Oscars afterparty in February 2008. "And then we ran into each other a week later, and that was that," she said. After they split months later, Mayer told TMZ, "I ended a relationship to be alone, because I didn't want to waste someone's time."

They would reunite and break up again before the end of the year, with Aniston saying during her Vogue interview, "It's funny when you hit a place in a relationship and you both realize, 'We maybe need to do something else,' but you still really, really love each other. It's painful." They gave it one more go in 2009 before going their separate ways. Mayer later suggested to Playboy that Aniston being eight years his elder had been an issue. "One of the most significant differences between us was that I was tweeting," he said. "The brunt of her success came before TMZ and Twitter. I think she's still hoping it goes back to 1998." 

Despite that shade, in 2020, a source told Us Weekly that the exes will always be there for each other. "Jen and John have a nice friendship," the insider dished.

Some reality TV fans didn't buy the romance between Brigitte Nielsen — who was once married to her "Rocky IV" co-star, Sylvester Stallone — and Public Enemy rapper Flavor Flav. As The New York Times reported in 2005, skeptics suspected that VH1 had orchestrated their relationship.

The couple first met while filming the VH1 reality series "The Surreal Life," with Flav admitting in a confessional that they didn't get along at first. In one scene, Nielsen smacked Flav on the face, and he slapped her back. She then laughed and said, "I like that." In a 2021 "Vlad TV" interview, Flav recalled being angry with Nielsen for touching his face. He also claimed she had a bad habit of not washing her hands after using the bathroom, saying, "Her hygiene wasn't all that." But he didn't object when Nielsen jumped into bed with him.

Flav and Nielsen's courtship took place in a house they shared with other celebs, including "Full House" star Dave Coulier and singer Jordan Knight. But the couple soon scored their own show, "Strange Love." After filming one season, they broke up in 2005. Flav moved on with his dating series, "Flavor of Love," and Nielsen married Mattia Dessi. When Flav learned that his ex was expecting a child at age 54, he had nothing but kind words for her. "It's amazing!" he told People in 2018. "It shows everybody in the world that everything and anything is possible. I was proud."

For "There's Something About Mary" star Cameron Diaz, there was just something about Good Charlotte rocker Joel Madden that she didn't see in his twin brother, Benji Madden. On Anna Faris' "Unqualified" podcast in 2021, Diaz revealed that Benji and his wife, Nicole Richie, helped bring her and Joel together in 2014. "They didn't set us up, but we were in the same room because of them, and then we found each other," she recalled. Diaz said she couldn't believe she hadn't noticed Joel before, but her fellow guest, Katherine Power, pointed out that she had interacted with his identical sibling. "They're not the same, they're so different," Diaz replied.

Diaz had previously dated multiple musicians, including Justin Timberlake, Jared Leto, and Diddy. But while Joel wasn't the first to capture her heart, he was the first to put a ring on it; the couple got hitched in January 2015. During the 2017 "In Goop Health" summit, Diaz revealed that she never really viewed any of her exes as being marriage material. "I've never had anyone who supported me so much and gave me so much courage to be myself," she said of Joel (via People).

After the couple welcomed their daughter, Raddix, in December 2020, Diaz revealed that watching Joel relish his new role as a parent made her love him even more. "He's such an amazing father," she said during a 2020 Instagram Live (via People). "I'm so lucky he's my baby's daddy."

At the 2016 Met Gala, Taylor Swift encouraged Tom Hiddleston to get up and dance. "And everybody else started dancing — which was great," Hiddleston recalled on the "BBC Radio One Breakfast Show" (via The Sun). Weeks later, the "Shake It Off" singer and the "Thor" actor were photographed kissing on the beach.

For a brief period of time in 2016, Hiddleswift was the celebrity relationship of the summer, although some fans seemed baffled by the pairing; there was just something about seeing Hiddleston wearing an "I [heart] T.S." tank top that made absolutely no sense to many people. He made the sartorial choice during Swift's star-studded Fourth of July party. By that time, the couple had attended a Selena Gomez concert together and vacationed in Rome. But while their affection for each other was obvious, Hiddleston found himself having to deny speculation that they were faking their romance for publicity. "The truth is that Taylor Swift and I are together, and we're very happy," he told The Hollywood Reporter later that July.

The couple's romance lasted a mere three months, after which, we finally got answers about that tank top. Hiddleston told GQ that he'd scraped his back, so one of Swift's pals offered him the garment to cover up the injury. "The friend pulled out the 'I [heart] T.S.' tank top that Taylor's friends are contractually obligated to own. And we all laughed about it. It was a joke," he explained.

Meghan Trainor's future husband was just a child when he gained fame. But when the "Mother" singer first spied "Spy Kids" star Daryl Sabara at a Hollywood party, he was a man. "I went right to him and was like, 'Are you "Spy Kids"?'" Trainor recalled on "The Drew Barrymore Show" in 2022. "He was like, 'Yeah,' and was really nice." Trainor's singing career took off during the two years that followed that random meeting, making her a recognizable star as well. Then, fate brought the pair together again. Trainor befriended another former child star, Chloë Grace Moretz, who offered to set her up with Sabara when Trainor said that she desperately wanted to date someone nice. "She's like, 'My best friend's the nicest guy,'" Trainor recalled. "And then we went on a double date, and we've never been apart ever since." The fourth party on that date was Moretz's boyfriend at the time, Brooklyn Beckham.

Sabara instantly knew he was done with the chase when he first laid eyes on the woman who blessed us with "All About that Bass." He told People, "It's super cheesy, but when you know, you know. ... We went from zero to 60." He was even willing to get to know his bae better by joining her on her tour bus.

The happy couple tied the knot in December 2018 and announced that they were expecting their second child together, another baby boy, in 2023.

It's dangerous to incite the wrath of the cunning Queen of the North, but Sophie Turner's marriage to Joe Jonas probably isn't part of a devious plot to take him down. After all, the DNCE member had no idea that he'd done something to anger the "Game of Thrones" star when they first started dating. In a 2020 interview with Elle, Turner said that she was a big fan of the pop-punk group Busted growing up, and she and her friends were convinced that the band split up because the Jonas Brothers covered their track "Year 3000." It became a huge hit for the Jo Bros, and apparently, Turner's posse believed that Busted found this unbearable. "It was all the Jonas Brothers' fault. So we hated them," she said.

But in 2016, she met Joe's agent, who told her that she and the singer would likely get along. Joe apparently believed this as well, as he soon slid into her DMs. "When I told my friends, they were like, 'Yes! Joe Jonas! That's hilarious. You have to do it,'" she recalled. Turner agreed to meet Joe at a dingy Camden dive bar while he was in England. "I thought he would be such a d***," she said. Instead, the singer's agent turned out to be right.

After three years of dating, Turner and Joe got married in 2019. They've since welcomed two daughters, whom Turner can introduce to Busted's music someday.

When "Stranger Things" star David Harbour caught the eye of "Smile" singer Lily Allen, she'd never watched his hit Netflix series. In a March 2023 appearance on "The Jonathan Ross Show," the British performer said she matched with Harbour on the Raya dating app. He was dressed like his "Stranger Things" character, police chief Jim Hopper, in his profile pic. "I thought he was just like a sexy policeman from a reality TV show because he was wearing a policeman's uniform," Allen confessed (via Digital Spy).

Allen didn't expect to find love with the American actor but soon found herself experiencing a magical first meeting straight out of a movie. "He was sitting underneath a clock. It was a bit like that moment in 'Titanic,' where [Jack] turns around under the clock," Allen recalled. The couple was first spotted attending a play at the Piccadilly Theater in London in 2019, but it's unclear if said clock was located in the venue or somewhere nearby.

Allen has two children from her marriage to Sam Cooper, daughters Ethel and Marnie. On "Jimmy Kimmel Live!" in 2021, Harbour said he once overheard the girls discussing whether he was their dad, stepdad, or something else. After Ethel, who is older, told Marnie, "'He's just some guy in our lives,'" Harbour recalled, "I was like, 'I need to marry this woman.'" And in a September 2020 Instagram post, he revealed that he and Allen had tied the knot in Vegas. 

More than a decade before Taylor Swift was penning breakup songs that had fans seeking the identities of the famous men who inspired them, Alanis Morissette had '90s alt-rock fans doing the same. In the 1995 classic "You Oughta Know," Morissette uses some explicit language to remind her ex that he made a vow to love her forever — and now her song lives on as a reminder that he broke this vow and broke her heart. As fans and the media tried to determine the identity of the heartbreaker, it became evident that the most likely culprit was the most unlikely guy to inspire such passion and rage: "Full House" actor Dave Coulier.

When Morissette appeared on "The Howard Stern Show" in 2004, she confirmed that she and Coulier dated, saying that they met during a hockey game. She wouldn't reveal if the song was about him but did say of its inspiration, "I didn't write it with the intention of recriminating him."

But Coulier is pretty certain that he inspired at least some of the lyrics in the song. On SiriusXM's "Jim Norton & Sam Roberts" in 2022, he recalled thinking, "Oh no. Oh, I can't be this guy," when he heard it on the radio for the first time. He even once asked Morissette what he should say when he gets asked about the song. "She said, 'You can say whatever you want,'" he recalled. "So, she was really sweet about it."