15 Couples We Definitely Never Saw Coming

With the rate that Hollywood stars go through relationships (and marriages), it is at times hard to keep up with who is dating whom and why so and so broke up. Save for the biggies like your Brangelinas, pairings from the past often fade into the back of the mind unless there is some reason to remember them. But sometimes, Hollywood couples are so weird that they are impossible to forget, even years later. For instance, Kelis and Bill Murray are reportedly dating, per gossip pages like Page Six, and no matter how long or short this relationship, it will be ingrained in our minds because of how random it is. Seriously, so random.

Some celebrities — like Heidi Klum or Taylor Swift, for instance — simply have unexpected taste in partners, so no one they choose is a real shocker. Others, like David Spade (who has dated Naya Rivera, Julie Bowen, Heather Locklear, and many other very attractive women) have had so many WTF relationships that it is no longer surprising when they have a new one. Then there are those weird couples that may not make sense on paper, but that actually don't seem so bizarre after some critical analysis, like Kanye West and Julia Fox. This list is made up of partnerships that made the culture collectively go "hmmm," due to huge age gaps, a large shift in "type" from previous exes, perceived personality and vibe differences, or something else entirely. Here are 15 couples we truly never saw coming.

Matthew Lawrence and Chilli are two 1990s stars we would never have paired together

Matthew Lawrence has not acted in a high-profile production in quite some time, but he had maintained a presence in the tabloids in recent years due to his relationship with "Dancing with the Stars" dancer Cheryl Burke. Lawrence and Burke married in 2019, after reconnecting in 2017, a decade after their first try at dating. Burke filed for divorce in early 2022 and has alluded to Lawrence cheating on her (but has not explicitly said so). Regardless of what happened, we expected Lawrence to fade back into the background without Burke's star power. But then, he entered into a relationship we never saw coming. Seriously, who would have predicted that the middle Lawrence brother from "Boy Meets World" would land the "sexy" in "CrazySexyCool?"

Rozonda Thomas, better known as Chilli from the iconic girl group TLC, and Lawrence were first seen out together in Hawaii in August 2022. Her rep said they were just friends, but by November of that year, they were confirmed to be dating. Soon enough, they were posing on Instagram in matching onesies and being photographed around Los Angeles being all lovey-dovey. In March 2023, Lawrence told "Entertainment Tonight" that he wanted to have kids together, but Chilli quickly clarified that they are not currently trying for a baby. She has alluded to the door being open to that after marriage, however somebody may want to tell her that she's in her 50s. We know she looks a decade younger, but Thomas's baby-making years are quickly dwindling.

Chelsea Handler and 50 Cent unexpectedly dated for a couple of months

When she first became really famous, Chelsea Handler was dating Ted Harbert, who happened to at the time be the head of E!, the network where her late-night show "Chelsea Lately" aired. The pair were together from 2006 to 2010, and Handler's dating life has been a hot topic ever since. After Harbert, Chandler spent two years in an on-off (mostly on) relationship with wealthy hotelier André Balazs. Handler most recently dated comedian Jo Koy, who she knew for decades before things turned romantic. Businessmen and comedians are expected partners for Handler, though, since she herself is a businessperson and a comedian. Animal trainers and rappers? Less predictable choices.

Let's start with the animal trainer, Dave Salmoni. It was a bit of a surprise when Handler started seeing the handsome TV personality, who has hosted shows such as Animal Planet's "Into the Pride" and "After the Attack." But her months-long fling with Salmoni was only a mild shock compared to Handler's other 2010 fling. We were truly flabbergasted when we learned that Handler and rapper 50 Cent dated, if only because Handler seems to take nothing seriously, while 50 and humor don't really go together in the same sentence. The odd couple dated for only two months, and though Handler has said they kept everything casual, she has also referred to him as her favorite ex-boyfriend. "I love 50 Cent, he was fun. He was just a sweetheart, and he was fun to be around," she told ET Canada.

Gwen Stefani and Blake Shelton are country meets pop

In no world would we have ever predicted that Gwen Stefani and Blake Shelton would become one of Hollywood's hottest married couples. For one thing, they were both married when they met as judges on "The Voice" in 2014. By the next year, they were both divorced and leaning on each other for support. Still, we did not see things moving beyond friendship because of how different the two are, at least in terms of their public persona. Shelton is a country singer who loves his ranch, his alcohol (his red cup of vodka was a running joke on "The Voice"), and his low-key lifestyle. Stefani is flashy and fun, known for sparkles and sequins and for being the ultimate Orange County girl. On paper, it definitely does not make sense.

But it seems to work for the pair, who started officially dating in November 2015 and married in July 2021. The years have proven that opposites not only attract, but they also sometimes even rub off on each other. Shelton has become a doting stepdad to Stefani's three sons — which he told "Today" helped him see he was "more than just a country singer" — and Stefani has embraced a quieter life on the ranch, where she has fallen in love with gardening. Heck, Stefani has even started recording country music with her now-hubby — a far cry from the ska-pop she is known for. We can't help but root for them...as long as Stefani doesn't quit music and move to Oklahoma permanently.

Before Keith Urban, Nicole Kidman almost married Lenny Kravitz

With his feather boas, leather pants, and piercings, Lenny Kravitz has always felt like the king of cool. At nearly 60, he remains one of the biggest zaddies in Hollywood and has more sex appeal than many men half his age. Kravitz was famously married to Lisa Bonet — mother to his one kid, the equally cool Zoë Kravitz — and dated people like Madonna, Vanessa Paradis Naomi Campbell, and Adriana Lima in the years after his divorce. So, we had gotten used to Kravitz choosing women with a little edge, and then he went and got involved with Nicole Kidman, totally throwing us for a loop. Kidman is an incredible actor, but she has always come across as far more buttoned-up than Kravitz (and we are not talking about the man's unbuttoned shirts, which he loves to wear to show off his amazing abs).

So, yeah, Kidman is not exactly the epitome of cool or edgy, but she is beautiful and talented and we see the appeal. The pair publicly denied their romance after speculation developed in 2002, when they became friendly after Kidman rented an apartment from Kravitz. They fessed up to being together a few months later, but we had no clue they were engaged until Kidman let it slip in 2017. The relationship only lasted from 2002 to 2003, so it is unclear for how long the duo were engaged. Kidman went on to marry country singer Keith Urban, a more predictable match, in 2006, while Kravitz remains unmarried.

The coupling of Kim Kardashian and Pete Davidson came out of nowhere

Pete Davidson's romances do not surprise us, at least not anymore. Whether you are onboard the Davidson train or not, it has become very clear that something about the comedian attracts a wide array of women. He has been linked to everyone from Kaia Gerber to Kate Beckinsale to Phoebe Dynevor, so we no longer make any predictions about Davidson's dating life, aside from the fact that it will keep us on our toes. But Kim Kardashian has always been rather predictable in her choices of men. She favors athletes and musicians and has not really had high-profile romances with anyone outside of those categories. Kardashian has also demonstrated a liking for a certain physical type — muscles, dark skin, classically handsome — and Davidson is very much not that.

Perhaps that is why the entire Internet was shocked when Davidson became Kardashian's first post-Kanye relationship. The age difference and very different life stages also led to the surprise, since Kardashian has four children and Davidson is not yet 30 and definitely does not seem like he is ready to step in as a dad figure. The pair met when Kardashian hosted "Saturday Night Live," and even kissed during one of the episode's most talked about skits. "When we kissed, I was just like, 'Hmm!' It was a stage kiss, but it was still like, a little zing," Kardashian said on the podcast "Not Skinny But Not Fat". The couple dated for nine months before parting ways in August 2022.

Zac Efron and Michelle Rodriguez had a short fling in 2010

Because he has been famous since he was a teenager, Zac Efron's dating history has been well-documented. He was with his "High School Musical" co-star Vanessa Hudgens for five years, until 2010, and was then linked to Lily Collins for a beat in 2012. Hudgens and Collins have similar vibes, but Efron's next documented relationship was with Michelle Rodriguez, who seems nothing like those other women. At 44, Rodriguez is significantly older than Efron and while 2023 Efron is buff and bearded, 2014 Efron was not yet at his muscled peak. While Hudgens and Collins read like dainty flowers, Rodriguez could totally kick Efron's butt — certainly back when they dated, and probably even now. It was a weird pairing, and we are not surprised it fizzled out quickly.

Efron and Rodriguez were first linked in the summer of 2014, when he was 26 and she was 36. After paparazzi caught them kissing on July 4th, media started diligently tracking the two-month relationship. For instance, paparazzi caught them making out in Ibiza in early August, and documented Efron's July 20 sleepover at Rodriguez's pad. People could not get enough of the odd pair, but by the end of the summer, Rodriguez had enough of Efron. Per Us Weekly, Rodriguez called things off so she could be on her own, while Efron supposedly still had feelings for the action star. Efron's subsequent dating life has been relatively predictable, while Rodriguez (who has also dated Cara Delevingne and Colin Farrell) has become increasingly private about her dating life.

Brigitte Nielsen and Flava Flav had a reality show documenting their love

On their own, rapper Flava Flav and actor/model Brigitte Nielsen are both lovably odd but put them together and the strangeness is almost overwhelming. We know this to be fact because the pair documented their short-lived, eccentric love affair on the VH1 reality show "Strange Love." The 2005 series lasted only eleven episodes, which is not that much shorter than Flav and Nielsen lasted as a couple. We are glad that somewhere out there, a reality television producer decided their antics needed to be documented for posterity, but we don't recommend "Strange Love" if you are looking for any sort of coherent storyline. Then again, Flav and Nielsen have both demonstrated a flair for reality TV — in fact, that is where they first met.

The couple began their romance after meeting on "The Surreal Life," another VH1 show from that era. Nielsen was famously once married to Sylvester Stallone, but admitted in a 2018 People interview that she's dated "some strange men." Enter Flav, who Nielsen was with for a year until she decided to be with Mattia Dessi instead. Nielsen and Dessi unofficially married pretty much directly following her split from Flav, and they made things legal a year later in 2006. When Nielsen announced she was pregnant in 2018 — at age 54 — Flav had nothing but love to send her way. "All I want to see is her happy and everything she wants in life," he told People. "She's good to people. That's why we clicked."

Linda Hogan inexplicably dated Charlie Hill, who went to school with her kids

We suppose Linda Hogan and Charlie Hill are not that shocking on the surface. After all, if men like Alec Baldwin and Richard Gere can marry women decades younger than them without people batting an eye, Hogan can certainly have a fling with a dude 29 years her junior. While the age difference was not so much the issue on its own, that Hill was only 23 made him appear somewhat like a child, and that was the weird part. Also bizarre? Hill was at one time a classmate of Hogan's kids, which had to have made for some awkward family dinners. "It was weird just because, to hear his name, Charlie Hill, I was used to hearing it around my school," son Nick Hogan said in a 2010 "Nightline" interview (via Us Weekly).

Linda Hogan started dating Hill shortly after her split from wrestler Hulk Hogan, and before the divorce was even finalized. Their four-year relationship ended in 2012, after which Hill sued Hogan for $1.5 million, claiming she made him do a ridiculous amount of manual labor. But before the split, Hogan was talking marriage and a future with Hill to just about any media outlet that would listen. Her ex-husband made a pretty odd choice with his next partner as well, choosing a woman who looked shockingly like his daughter to marry (and then divorce). This family in general has quite a few oddities, and don't get us started on those photos of Hulk applying sunscreen to his daughter's inner thighs.

Jonathan Scott and Zooey Deschanel had the public going huh?

A lot of these odd couples are being judged on our interpretation of their weirdness, but not so with HGTV star Jonathan Scott and actor Zooey Deschanel. When these two started a romance, the public reaction was hilarious, with the consensus being that the pairing was totally out of left field. The reaction was so vibrant that even Scott has commented upon it. "I don't think it was expected," he told People in January 2020. "You know, what's really funny to me is, yeah, you see online and on social media, the internet is obsessed and keeps posting [about us], but the funniest thing is everyone's like, 'She's dating who?!'" Something about the pairing clearly works because the couple is still going strong years later.

Both Scott and Deschanel are divorced, which might explain why they have yet to tie the knot after four years together. They met in 2019 while filming a segment for an episode of "Carpool Karaoke," and moved in together in 2021. Though they are unmarried, Deschanel has referred to Scott as "an amazing stepdad" to her son and daughter with ex-husband Jacob Pechenik (via People). Even though we did not originally see straight-laced Scott and quirky Deschanel as an ideal fit, we can't help but be on board with the relationship because of how sweetly they speak about each other. "I don't want too seem sappy or hyperbolic but the simple truth is: I'm the luckiest girl in the world," Deschanel said in a 2021 Instagram birthday post.

Strangers used to make comments to Emilia Clarke about Seth MacFarlane

People are emboldened on the internet and often say things they would not say to a person's face in real life. But when it comes to celebrities, who the public sometimes assumes have no feelings and are open to constant critique, perhaps they would have no trouble saying it. That is basically what happened to "Game of Thrones" star Emilia Clarke when she began dating "Family Guy" mastermind Seth MacFarlane. Despite the pair making a rather cute couple, people often felt the need to comment upon the pairing when Clarke was out in public. "Well, a con is you have strangers giving you love-life advice like, 'I'm a big fan of the show, and I'm not sure what you're doing with that guy,' which I didn't react well to," she said in a Glamour interview. "That happened in New York when Seth and I were together. This guy started to give me advice: 'Can I get a selfie? And by the way...' Unh-unh, bro."

Public reaction aside, Clarke and MacFarlane appeared to be quite into each other when they were dating. Both stars are very private about their love lives, and the 2016 Glamour interview is one of the only times either of them has spoken about the relationship. We do know they were already a couple in September 2012, when they were spotted leaving an HBO event together, and Us Weekly reported they had been dating for months by that point. MacFarlane and Clarke, who have a 14-year age difference, split the following March.

Elisabeth Moss has not spoken well of her marriage to Fred Armisen

Like Emilia Clarke and Seth MacFarlane or Zac Efron and Michelle Rodriguez, Elisabeth Moss and Fred Armisen are another example of a couple with a big age gap and very different public personas. File them in the same pile as Amber Tamblyn and David Cross in that they are unexpected matches but not off-putting or stomach-turning. But unlike Tamblyn and Cross, who remain married, Moss and Armisen did not go the distance and Moss has not had the best things to say about her ex-husband. "Looking back, I feel like I was really young, and at the time I didn't think that I was that young," Moss said in a 2014 Vulture interview. "It was extremely traumatic and awful and horrible. At the same time, it turned out for the best."

Like we said, goofy funnyman Armisen always seemed like an odd choice for Moss, who is funny enough in interviews but best known for her extremely dramatic roles in fare like "Mad Men" and "The Handmaid's Tale." The pair met on the set of "Saturday Night Live," when Moss was a guest in a sketch on an episode hosted by her "Mad Men" co-star Jon Hamm and Armisen was an "SNL" cast member. They were together only three months before getting engaged (always a good call, right?) and married in October 2009, a year after they first met. They split the following September, which makes their marriage one of the briefer ones in Hollywood history but is certainly not the shortest of all time.

Meghan Markle was not the expected choice for Prince Harry

There is not much that has not been said about Meghan Markle and Prince Harry by this point, and collectively, it seems like we have agreed to move past the oddness of their pairing. At the time they got together, however, the "Suits" actor was ripped apart by both the media and public alike. Much has happened in the years since they got together, and many royalists still feel that Markle was the wrong choice for the handsome British prince. But two kids and a whole exodus later, the couple is going strong and are proof that it really does not matter what others think as long as you and your partner are confident in the relationship.

Markle met her (literal) prince in July 2016 when they were introduced by mutual friends and before when announcing them as a couple that November, Harry also condemned the rude — and often racist — comments flying Meghan's way. "We're a couple. We're in love," Markle said in a Vanity Fair interview the following September. "I'm sure there will be a time when we will have to come forward and present ourselves and have stories to tell, but I hope what people will understand is that this is our time. This is for us. It's part of what makes it so special, that it's just ours. But we're happy. Personally, I love a great love story." The couple wed in May 2018 and despite the outside chaos, have built a solid foundation for themselves and their two kids.

Katharine McPhee is younger than David Foster's adult daughters

Katherine McPhee and David Foster first met when she was a contestant on "American Idol" and he was a guest mentor, all the way back in 2006. Foster played piano when McPhee married her first husband Nick Cokas in 2008 (strange in itself) and the two were not linked again for almost a decade. They made their public debut in 2016 and, even though both of them had divorced their partners by then, played it coy for a while before confirming their relationship. They were engaged in July 2018 and married the following June, when McPhee was 35 and Foster was 69. "I totally get the judgment initially, but things are never as they appear, things are never exactly as they appear and I'm in love with our love story and that's all that matters," McPhee said on "Dr. Berlin's Informed Pregnancy Podcast".

We have established that age differences are not, on their own, always odd, but this one certainly is peculiar, if only because Foster has children older than his current wife. That said, McPhee appears to have a great relationship with Foster's grown children, though two of his more public daughters, Erin and Sara Foster, have not shied away from poking fun at her. "You ever side-planked with your 37-year-old stepmom?" joked Erin Foster, who is two years older than McPhee, on an April 2021 Instagram story (via Us Weekly). In February 2021, McPhee gave birth to son Rennie, and later that year, the couple competed on "The Masked Singer" as the banana split.

Cher proved she can still shock us when she began dating Alexander Edwards

Once upon a time, Cher choosing a much-younger man would not have surprised us in the slightest. Cher has dated a slew of men significantly her junior, including actor Val Kilmer (a 13-year age difference), producer Josh Donen (an 11-year age difference), and baker Rob Camilletti, who was only 22 when he started dating a then-40-year-old Cher. Her fling with Tom Cruise was somewhat baffling, not because of their 15-year age gap, but because Cher is just so much cooler than him. But even then, that was back when we expected Cher to shock us. The pop legend is now 77 and we had not heard a peep about her love life since she split from Ron Zimmerman in 2010 (himself more than a decade her junior).

Pardon us for thinking Cher was done with romance, because she proved she can still produce a surprise when she started dating music executive Alexander Edwards in 2022, after they met during Fashion Week in October 2022. Even Cher seemed to know how odd it was that she was dating a man four decades younger than her, admitting on "The Kelly Clarkson Show" that "On paper, it's kind of ridiculous". Alexander once dated Amber Rose (with whom he has a child), so Cher was an odd choice for him as well, based on type. And yet, the way Cher spoke about the relationship convinced us to get onboard. Sadly, the couple broke up in may 2023 after only six months together.

Shailene Woodley and Aaron Rodgers never quite made sense

We can't say that Shailene Woodley and Aaron Rodgers are one of the oddest matches on this list, but their relationship always felt a bit puzzling. Woodley is a super earthy actor who makes her own deodorant and pens op-eds for Time advocating for environmental causes. Rogers, on the other hand, is a professional athlete who seems more fit for a car show than the forest. "They disagreed on a lot of things. Early on, they decided to agree to disagree about things and not debate them," an anonymous source told People in 2022. While disagreeing about fundamental political and social issues is not necessarily a recipe for disaster, simply avoiding certain topics is not a sustainable strategy.

Rodgers and Woodley were first linked very soon after the NFLer split from race car driver Danica Patrick, his partner of two years, causing some gossip sites to speculate about possible cheating. That was in July 2020, but the couple was not confirmed to be dating until February 2021. Only days after an anonymous insider confirmed the relationship, Rodgers himself announced their engagement at the NFL Honors Awards. They split up a year later, and Woodley has since expressed her discomfort with the public attention, especially on Instagram. "It was the first time that I'd had a quote-unquote 'famous' relationship, and I watched [the] scrutiny, opinions, the desire for people to know my life and his life and our life – it just felt violating in a way that, before, it was fun," she told Net-a-Porter.