He Dated Her?! 50 of the Most Unlikely Celebrity Pairs

It’s not news that celebrities like to keep things familiar and date fellow Hollywood stars. But there are star couples who totally make sense, like Will Smith and Jada Pinkett-Smith or Ashton Kutcher and Mila Kunis. But then there are couples who are totally unlikely, who make heads turn (and not in the best kind of way). These are couples who make people go “Whaaaa?”

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And the following list of couples aren’t only oddly paired (like Chelsea Handler and 50 Cent), there are some that are only shocking because no one ever heard they were dating (such as Natalie Portman). Yes, folks, this is gonna be a fun list. So, grab the popcorn (or your friends) and see which unlikely couple is the most surprising!

Macaulay Culkin and Mila Kunis

We all know the That ‘70s Show star as being the beautiful wife of fellow co-star Ashton Kutcher, but not much is known about her dating life before him. Well, to those who had no idea, it might come as a surprise that she and the Home Alone star, and former child actor Macaulay Culkin, used to be an item.

Macaulay Culkin and Mila Kunis posing in front of Black and Decker appliances

Photo by Diumitrios Kambouris / WireImage / Getty Images

The pair dated for a long time, too, between 2002 and 2011, but they tried to keep their romance on the down-low. While you might think he was the one who wanted to get her attention, it was the other way around. “He was huge. You couldn’t walk down the street with him,” Kunis said. “Fans just screamed when they saw him!”

Amy Poehler and John Stamos

Here’s another couple many people either didn’t know about or find basically just find an improbable pair. Poehler admitted to Howard Stern on his radio show that after she split up with her husband Will Arnett, she “rebounded” with the former Full House star.

Amy Poehler posing for a portrait while arriving at an SNL after party / John Stamos backstage leaning on a pole next to the stage

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Poehler explained: “He did a little bit in a movie that I did and a bunch of us hung out. And then later on he’s like, ‘Let’s go get dinner. And it was fine. I remember thinking like, ‘Oh, s–t. Like, if this is really a date…’” She said she was wearing a Leslie Knope top and revealed to Stern that no, she didn’t sleep with Uncle Jesse.

Grimes (Claire Elise Boucher) and Elon Musk

When the Tesla CEO and out-of-this world genius and musician-producer walked the red carpet together in May 2018, people were shocked. But they’re apparently not as opposite as we think they are. They share a similar sense of humor and a fascination with artificial intelligence.

Elon Musk and Grimes dressed up on the red carpet

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It’s something they discovered when they first connected on Twitter. It didn’t take long for this couple to skip the conventional route of getting married. They moved right on to having a baby. Their kid’s name? X Æ A-12 Musk. No, it’s not a joke. That’s the baby boy’s actual name. How do you pronounce? Your guess is as good as mine.

Edward Norton and Courtney Love

I don’t know about you, but I do not remember these two being an item. And they even dated for three years! We can safely say that Edward Norton is a far cry from Kurt Cobain (who was more of her type). They met on the set of the film, The People vs. Larry Flynt and were even reported to have been engaged.

Courtney Love, Woody Harrelson, and Edward Norton posing at the end of a ramp leading up to a plane

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But they didn’t end things on good terms (surprise, surprise). Love called him out on Twitter in 2010, claiming that he still owes her $300,000. Although still bitter, she did note that “I’ve got to give it up to Edward Norton for teaching me about acting and about philanthropy.”

Brad Pitt and Christina Applegate

At the time, Applegate was a big star on Married with Children and Pitt had a small part on Knots Landing. She took him to the 1989 MTV Movie Awards where she allegedly dumped him and left with someone else!

Christina Applegate and Brad Pitt dancing on the red carpet

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Funny thing is that Applegate went on to play Jennifer Aniston’s sister on Friends (when Aniston was married to Brad). When she was asked who she left America’s sexiest actor for, she remained tight-lipped about it. All she said was that he wasn’t an actor, but he was known to the public. Oh, the curiosity!

Natalie Portman and Moby

These days, the adorable actress is married to choreographer Benjamin Millepied with whom she has two kids. But there was a time where the young actress was dating eccentric music artist Moby. Of their short-lived romance, Moby said, “As far as the very brief affair that I had with Natalie, it’s made me a target of a lot of nerd wrath.”

Moby and Natalie Portman holding a cake

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He continued by saying, “You don’t date Luke Skywalker’s mom and not have them hate your guts.” The man has a point. Now, the next couple involves Portman’s co-star from the awesome indie film Garden State…

Zach Braff and Florence Pugh

Only Scrubs fans might know this, but for the rest of us, seeing Zach Braff and Florence Pugh together was a little surprising. The Scrubs star and the Little Women star started going out in 2019. An Instagram user pointed out their 21-year age difference, writing, “@zachbraff you’re 44 years old.”

Zach and Florence posing together in a selfie / Zach and Florence standing and posing in a desert looking area

Source: Instagram / @zachbraff

Pugh saw the comment and replied with, “And yet he got it.” The couple quarantined together in Los Angeles. Braff is 45 and Pugh is 24. After seeing all the online hate regarding their ages, Pugh said, “It makes me upset that during this time when we need to be together, the world is aching and the world is dying, and a few of you decided to bully for no reason.”

Evan Rachel Wood and Marilyn Manson

It’s not surprising that Evan Rachel Wood has a dark side, but when it became public that she was dating the controversial music artist Marilyn Manson in 2007, her fans were utterly shocked. The Westworld star was just 18 years old at the time, and Manson was, well, 18 years older. AND he was still married to Dita von Teese at the time.

Marilyn Manson and Evan Rachel Wood posing in front of a piece of artwork

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They dated for a while and even got engaged in 2010, but they broke off the engagement later that same year. Apparently, Manson’s song “I Want to Kill You Like They Do in The Movies” was written about Wood.

Janet Jackson and Matthew McConaughey

Alright, alright, alright. So, who here knew that Janet Jackson and Matthew McConaughey were once an item? Apparently, the two dated back in 2002, after hitting it off at the Grammy Awards. They didn’t last long, though. Jackson eventually confessed to the fling before she hooked up with Jermaine Dupri.

Janet Jackson and Matthew McConaughey embracing and smiling at each other

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Some reports stated that McConaughey was spotted leaving Jackson’s house the morning after the awards ceremony carrying his shoes. McConaughey said, “I met her at the Grammys and found her to be a very, very sweet lady. We swapped some good music and she’s a dear lady. She’s a sweetheart but we’re not dating, we’re just friends.”

Rashida Jones and Tobey Maguire

These two dated from 1997 to 1999, before either of them were big Hollywood names. And there’s even a report that says they were even engaged. As the story goes, Maguire broke up with Jones. The quirky couple called it quits in 2000, right before Maguire became a household name with the Spiderman franchise.

Toby McGuire on the red carpet / Rashida Jones on the red carpet smiling

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It’s been a while since these two broke up. They have each been in the spotlight for their own careers. These days, Maguire is married to Jennifer Meyer, and they have two kids. Jones is also married, to Ezra Koenig from the band Vampire Weekend.

Drew Barrymore and Christian Bale

Bale revealed to GQ Australia in 2012 that he dated Barrymore once, but she was the one who “ghosted” him. “We went to see some bloody awful horror film, and that was the end of it,” Bale admitted. “She never called again.”

Drew Barrymore on the red carpet / Christian Bale on the red carpet posing with his arms crossed

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A few years later, during a 2015 appearance on Watch What Happens Live, Barrymore was asked why she ghosted Batman. “I don’t know! He was so nice. I wasn’t like super boy crazy. I had a lot of fish to fry, like I had big problems in my world for many years, like in good ways, things you gotta overcome… boys are like very secondary.”

Kate Beckinsale and Pete Davidson

The Underworld actress and the Saturday Night Live comedian were once an item, and yes, it’s one that had many, many people scratching their heads over. And their 20-year age gap was just one odd factor. According to an eyewitness, the two were flirting at an InStyle party, where she was following him around and waiting for him.

Kate Beckinsale on the red carpet in a red sequined dress / Pete Davidson on the red carpet

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This source told Us Weekly: “People approached her, and she didn’t want to talk to anyone else.” The two were later spotted holding hands in L.A. not long after that party. Another insider revealed to Us that Beckinsale “likes the fact that he’s younger than her.”

Megan Fox and Machine Gun Kelly

The fox from Transformers met the “Bad Things” rapper recently, in 2020, while she was filming the crime thriller Midnight in the Switchgrass. An insider source told Us in May 2020 that the couple is “officially dating” after Fox’s split from her husband Brian Austin Green.

Megan Fox and Machine Gun Kelly on the red carpet

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“They’re enjoying spending more and more time together and have a strong connection,” the source said. At first, this couple seemed unlikely, but the more you look at them, the more it makes sense!

Speaking of making sense, this next couple is more than just official. And none of it makes sense…

Tom Cruise and Cher

Tom Cruise sure knows (or knew) how to make the headlines. Before he ever jumped on Oprah’s couch to profess his mad love for Katie Holmes and create controversy with his faith, he made head turns because of the women he dated. And Cher was one of them.

Tom Cruise and Cher about to hug backstage at a concert / Chris Anderson, Tom Cruise, Bruce Jenner, Cher, Richard C. Strauss, and Robert Rauchenberg with Nancy Reagan at the White House

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The pair were dating back in the 1980s. Even back then, it was an odd match – just look at their height difference! Cruise and Cher never made it as a couple in the long run, but we can still have fun and imagine what their kids would have looked like.

Rihanna and Shia LaBeouf

LaBeouf revealed that he hooked up with Rihanna back in 2007, but he admitted that the affair was brief. “It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends,” he said in 2009.

Rihanna posing on the red carpet adjusting her hair / Shia LaBeouf posing on the red carpet with his hands in his pockets

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The actor has been romantically linked to a number of famous ladies who people might find unlikely, such as Carey Mulligan, whom he dated for about a year before calling it quits. He also dated Hillary Duff, Mia Goth, and his Honey Boy co-star FKA Twigs.

Kat Dennings and Josh Groban

In 2016, news surfaced that Dennings and Groban were calling it quits after dating for two years. It only prompted people to respond with, “Those two were dating?” Actress Kat Dennings and Grammy-nominated singer Josh Groban were, at one point, a fresh and unexpected couple. Now, they’re a past, and still unexpected, couple.

Kat Dennings and Josh Groban on the red carpet together wearing black

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They stepped onto the red carpet together in October 2014, to the surprise of many. Groban, who also dated Mad Men actress January Jones, told Entertainment Tonight: “I do have such a lovely date tonight,” referring to the star of 2 Broke Girls.

Christina Hendricks and Geoffrey Arend

Here’s another pair that fell off the radar. Mad Men’s Christina Hendricks, with her curvy figure and red hair, has been something of a sex symbol ever since her role as Joan Harris. It’s something her actor husband Geoffrey Arend (since 2009) thinks is funny.

Christina Hendricks and Geoffrey Arend with their dog cozied up under a blanket

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“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,” Hendricks told Cosmopolitan in 2012. “My husband has a good laugh about it, of course.” While they’re laughing at that, we’re laughing for, um, other reasons.

Kristen Johnston and Ryan Reynolds

There was a time when everyone’s favorite Canadian (aside from Ryan Gosling) dated Kristen Johnson, the former star of 3rd Rock from the Sun. Their union didn’t last, of course, but Johnston only has good things to say about her ex-beau.

Kristen Johnston and Ryan Reynolds on the red carpet in 1999

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“It was so long ago I forgot, but literally, so nice, great guy, lovely,” she told Andy Cohen. “Lovely person,” she added. The duo dated briefly in 1999, where people saw them at the premiere of The Green Mile together. Reynolds is now married to Blake Lively and they have three daughters together. Johnston appears to be single.

LeAnn Rimes and Tiger Woods

Tiger Woods is one of those famous dudes who’s so much of a ladies’ man that it basically left him disgraced and shunned from Hollywood. Of all his many, many women, country singer LeAnn Rimes was one of them, and an unlikely one at that.

LeAnn Rimes on the red carpet in a white v-neck dress / Tiger Woods holding his golf club

Photo by Sarah Morris, Getty Images / Rob Carr, Getty Images

With all the shade thrown his way, people forgot that the pro golfer dated the blonde singer. Woods is seven years older than Rimes, which is only one discrepancy between the two, their careers, and well, everything else. But one thing we do know is that Woods likes them blonde.

Katie Couric and Bob Saget

Couric confessed to Howard Stern that she went out with the Full House star and raunchy comedian Bob Saget, but love wasn’t in the cards for them. He “was really fun,” she said. “I had fun, I don’t think I did it for him.” As it turns out, Saget never called her back. “That’s alright,” she told Stern.

Bob Saget and Katie Couric in the news studio posing together

Source: Twitter

Couric also revealed other famous faces that she went out with at one point, like popular TV host Jeff Probst. She said she also didn’t hear again from Probst. “I can’t say that I was devastated that neither called me back,” she said.

Alanis Morissette and Dave Coulier

Speaking of Full House, did you know that Uncle Joey used to date Alanis Morissette? The “You Oughta Know” Canadian singer and Dave Coulier were an item once upon a time. Coulier stated that Morissette’s classic ‘90’s alternative rock song was about him. But only she knows whether that’s true or not.

Dave Coulier and Alanis Morissette on the red-carpet holding hands

Photo by Ron Galella / Ron Galella Collection via Getty Images

“No revealing,” Morissette said when asked about the inspiration for the song. “But I am intrigued at the thought—or at the fact—that more than one person has taken credit for it. I’m thinking, I don’t know if you want to take credit for being the person I wrote ‘You Oughta Know’ about.” The woman has a point!

Ellen Barkin and Johnny Depp

Before he famously dated Kate Moss, Depp was linked to actress Ellen Barkin in 1996 (when she was 40 and he was 30). Depp has said his Fear and Loathing in Las Vegas co-star Barkin accused him of being violent when they were dating.

Johnny Depp and Ellen Barkin on the red carpet in 1994

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Depp said he just wanted a casual fling, whereas she was looking for something more serious (how cliché). According to Depp, Barkin has been holding a “grudge” against him ever since. As we know, this wasn’t the first time Depp has been accused of violent behavior (his ex-wife Amber Heard claimed similar charges in 2016).

Helen Mirren and Liam Neeson

The two A-listers met on the set of Excalibur (Neeson’s first movie role) in 1980 and were an item until ’84. In 2014, Neeson told CBS: “Oh, my God. Can you imagine riding horses in shiny suits of armor, having sword fights and stuff, and you’re falling in love with Helen Mirren? It doesn’t get any better than that.”

Helen Mirren and Liam Neeson sitting on a large red sofa laughing during the filming of a talk show

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On meeting the actress, Neeson gushed about how quickly he fell for her on multiple occasions. He first saw Mirren on stage as Lady Macbeth and was infatuated with her. When he got to star alongside her in a film, he confessed that he was smitten with her.

Julie Bowen and David Spade

In his heyday, the little comedian David Spade dated a bunch of hot Hollywood blondes, like Heather Locklear and Nicolette Sheridan, but who knew that he dated Modern Family star Julie Bowen, too? The two were together for a year back in 2002.

Julie Bowen and David Spade on the red carpet

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Spade was filming his comedy Dickie Roberts: Former Child Star, when he met Bowen, who was working then as a voice artist for the animated show Justice League. In 2020, Bowen stated that she loves him and talks to him a lot and will say to his face, “he’s a lovely person and a good friend, not a great boyfriend.”

Ashley Olsen and Lance Armstrong

Sheryl Crow wasn’t the only star who dated, and was duped by, Lance Armstrong. The cyclist wrote a tell-all called Cycle of Lies, where he gave readers an inside look at his secret relationship with a much younger woman — Ashley Olsen. The age gap? 15 years.

Ashley Olson on the red carpet / Lance Armstrong in his biking gear

Photo by Jon Kopaloff, WireImage, Getty Images / Mark Mainz, Getty Images

Only weeks after Armstrong broke up with designer Tory Burch in October 2007, Armstrong and Olsen were spotted out on the town in New York City. An onlooker recounted that “Ashley drank red wine, sat on his lap and they were making out all night.” Their fling fizzled out within months.

Mary-Kate Olsen and Olivier Sarkozy

The former child star and fashion mogul started dating the French banker Olivier Sarkozy, which raised many eyebrows all over the world. Not only is he massively tall compared to her, he’s also 17 years older than her.

Marky Kate and Oliver cozying up in a private box at a tennis match

Photo by Uri Schanker / GC Images / Getty Images

The pair tied the knot in a private ceremony in New York in 2015, when she was 29 and he was 46, after three years of dating. Apparently, he was ready to marry her much earlier on, but for whatever reason, Mary-Kate decided to wait. Turns out, the two have already divorced.

And it looks like her sister likes the older gentlemen, too…

Ashley Olsen and Richard Sachs

Ashley, the other Olsen twin, followed suit and started dating a much, much older man. 31-year-old Olsen was with the 65-year-old financier and art-dealer Richard Sachs for a few months, during which they were spotted cozying up together several times.

Ashley and Richard laughing together at a basketball game in the stands

Photo by James Devaney / GC Images / Getty Images

Olsen decided to end their relationship because she (reportedly) wanted to focus on her work as a fashion designer, specifically on the brand Elizabeth and James. She and her sister own the brand, and it seems like fashion is just one thing that they share a taste for. (All I’m gonna say is “daddy issues.”)

Madonna and Michael Jackson

It may seem weird now, but Jackson actually dated a bunch of celebrity women in his heyday. One of them was Madonna, and in a 2016 bit with James Cordon on Carpool Karaoke, she admitted to hooking up with the king of pop in the early ‘90s.

Michael Jackson and Madonna on the red carpet at the Academy Awards / Michael Jackson walking behind Madonna checking her out

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She said that “he was a little shy.” The pair met in the early ‘80s thanks to Madonna’s manager Freddy DeMann, who was also Jackson’s manager. Madonna and Jackson made their first public appearance together at the 63rd Academy Awards in 1991. The media went wild.

Hugh Jackman and Deborra-Lee Furness

Every once in a while, we see the male celeb hand in hand with an older female celeb. Such was the case with X-Men star Hugh Jackman and his wife since 1996, actress Deborra-Lee Furness. The two met when Jackman was in his early 20s on his first acting job.

Hugh Jackman and Deborra-Lee Furness smiling on the red carpet

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It was an Australian TV show which starred his future wife, who’s 13 years older than him. Hugh said they fell “madly in love” and became a pair in no time. Unfortunately, she couldn’t conceive a child, and so the couple adopted two children.

Cameron Diaz and Benji Madden

This couple isn’t just in an “unlikely couple” list. They can also be found on the “she’s taller than him list.” Cameron Diaz and Good Charlotte guitarist Benji Madden married in 2015. She knew Benji’s twin-brother and fellow band-member, Joel Madden, and his wife, the socialite and fashion designer Nicole Richie.

Benji Madden and Cameron Diaz at an event standing in front of leafy bushes

Photo by Donato Sardella / Getty Images for REVOLVE

But Diaz didn’t meet Benji until she hosted a dinner party. Benji doesn’t fit the type of men Cameron has dated in the past (such as Justin Timberlake and Alex Rodriguez), but she says, “I’d never been loved in that way. I look at him every day, and he inspires me.” Aww.

Danny Boyle and Rosario Dawson

The 38-year-old actress Rosario Dawson dated the famed director Danny Boyle (who’s in his 60s) when they were working together on the 2013 film Trance. The two were involved in a short-lived, intense romance, and managed to keep their relationship under wraps.

Rosario Dawson and Danny Boyle posing together at an event

Photo by Jared Siskin / Patrick McMullan via Getty Images

“I love Danny. He’s wonderful and we dated longer than people think we did,” the actress said, adding that, “From the outside it looks like there’s a lot of dissimilarities, but we actually have a lot in common.” At least she acknowledges that they’re a questionable couple. Self-awareness is always a good trait to have.

Emilia Clarke and Seth MacFarlane

In 2012, the Game of Thrones star Emilia Clarke and the Family Guy creator, Seth MacFarlane, were spotted (and photographed) getting cozy together. Look, the guy is downright hilarious, but when you consider the fact that Khaleesi is thought of as one of the most beautiful women in the world, then you can see why many people have wondered how these two are romantically linked.

Seth MacFarlane and Emilia Clarke sitting at a table posing for the camera at a party

Photo by FilmMagic / Getty Images

Clarke spoke about how complete strangers have expressed their opinions about the bizarre-looking relationship, saying she didn’t appreciate it. Well, the couple ended things the following year. So…

Chelsea Handler and 50 Cent

There’s something cute about Handler’s and 50 Cent’s short-lived relationship. For those who didn’t see, the rapper was on Handler’s show, Chelsea Lately, which happened to be the first time they ever met. And it was evident to everyone watching that something clicked.

50 Cent and Chelsea Handler hugging him for a photograph

Source: Twitter

The audience enjoyed watching the two hit it off. They had such good chemistry on that episode that they ended up dating for a few months, but it wasn’t such a serious thing. 50 Cent also appeared on the Chelsea Lately finale where she asked the rapper, “Seriously, are you over me?”

Hugh Hefner and Crystal Harris

Most people are a little shocked when they see photos of this couple, for obvious reasons. Without speaking badly of the late Playboy mogul, we’ll just say that young blondes were part of his game.

Hugh Hefner and Crystal Harris on the red carpet posing together

Photo by Michael Caulfield / WireImage / Getty Images

Harris was actually his third wife, and they were married until his death in 2017 at the age of 91. They were married for five years – the last five – of his long and colorful life. Oh, and by the way, Harris was only 25 when the two walked down the aisle. Hefner? Well, um, he was 86.

Simon Cowell and Carmen Electra

Their union was brief, but Carmen Electra and Simon Cowell indeed had a thing going on for a while back in the day. We can all admit that it’s hard for us to imagine them together. And really, it’s mostly because of Simon’s – let’s say unfriendly – personality.

Carmen Electra and Simon Cowell on the set of American Idol

Photo by Ray Mickshaw / WireImage for Fox Television Network / Getty Images

That said, it’s hard to imagine him with anyone. Can you just picture him critiquing the way his date eats dinner on a date? Both of them downplayed their romantic involvement, but Electra and Cowell were hot and heavy for about six months, believe it or not.

Britney Spears and Colin Farrell

For some reason, seeing these two together doesn’t add up. Regardless of our opinions, Spears was with Farrell in the early 2000s.

Britney Spears and Colin Farrell on the red carpet laughing at something or someone behind the camera

Photo by Kevin Winter / Getty Images

In 2003, Spears and Farrell shocked the world when they showed up at the premiere of The Recruit together. They walked down the red-carpet holding hands and were spotted engaging in some serious PDA (public display of affection). But then again, he said, “She’s just a mate. Seriously, we just met a week ago, (we’re) having a laugh.” Meanwhile, she called him “an amazing person.”

Kirsten Dunst and Jesse Plemons

Peggy and Ed Blumquist played a pair of high school sweethearts on the series Fargo, but no one actually expected their relationship to evolve into a real-life romance. After Dunst split up with Garrett Hedlund after four years of dating, she moved on to dating her co-star, Jesse Plemons.

Jesse Plemons and Kirsten Dunst on the red carpet together smiling

Photo by Gregg DeGuire / FilmMagic / Getty Images

They didn’t just have a fling, though. They actually fell in love and had a child together. The couple welcomed a baby boy in May of 2018. They’re currently engaged but no date has been set for their future wedding.

Sarah Paulson and Holland Taylor

Talk about age difference! Sarah Paulson came out as part of the LGBT community in 2005, which wasn’t such a shocker, and nobody really made a fuss. But when she started dating Two and a Half Men actress Holland Taylor, you could believe that people were stunned.

Sarah Paulson and Holland Taylor posing together on the red carpet

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And it’s because Paulson is 43 years old whereas Taylor is 75. Paulson said people told her their relationship might damage her career. “When people found out I was with Holland, some said: ‘I think you have to be careful, I’m afraid it’s going to affect your career negatively.’” But the great thing about Paulson is that she doesn’t care what people think!

Ashton Kutcher and January Jones

1998 was a good year for Ashton Kutcher: He landed the role of his career as Kelso in That ’70s Show and started dating the beautiful up-and-coming actress January Jones. At the time, she was known as a model.

Ashton Kutcher hugging January Jones for a pose on the red carpet

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How, exactly, they met is unclear, but it’s likely that they ran into each other in their inner Hollywood circle. In 2000, People reported that the duo was living together in L.A., so they were together for at least a couple years. But, as we know, Kutcher went on to be happily married to Mila Kunis. And unlike these two, he and Kunis just make so much sense.

Courteney Cox and Michael Keaton

In 1995, in a cover story for People, Courteney Cox was quoted as saying that her relationship with Michael Keaton was “the most important relationship I’ve ever had, and he is the most wonderful person I’ve ever met.”

Courteney Cox and Michael Keaton on the red carpet together

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At the time, they had been a couple for more than five years and had only parted a few months prior. They started going out in 1989, calling it quits in 1995. As with many of the couples on this list from the ‘80s/’90s, let’s remember that it was pre-Internet, so we weren’t bombarded with the amount of Hollywood gossip we see now.

Owen Wilson and Sheryl Crow

Comedic actor Owen Wilson and singer Sheryl Crow were an item from 1999 to 2001. It’s been a while, so Crow has been able to look back at her past relationships (including one with Lance Armstrong) with some clarity.

Owen Wilson and Sheryl Crow posing on the red carpet at a movie premiere

Photo by Jim Smeal / Ron Galella Collection / Getty Images

In an interview with Good Housekeeping, she said that she’s always gone out with “guys who were highly successful, which would seem like it would put me at an equal level… but what ends up happening is that one of you becomes smaller – and it was always me. I do think that sometimes in order for one person’s light to shine, everyone else has to dim theirs.”

Sandra Bullock and Ryan Gosling

It’s not that these two are so unlikely, it’s that who remembers them ever dating!? Well, they did, and it happened after they met on the set of the 2002 film Murder by Numbers. They went out for a few months. In 2011, Gosling recalled this time with Bullock fondly.

Ryan Gosling and Sandra Bullock smiling on the red carpet together

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If there is anything that makes them a couple, it’s the fact that Bullock is a full 15 years older than Gosling. While they made for a good-looking couple, they received several raised-eyebrow comments over their age gap.

Robert Downey Jr. and Calista Flockhart

The Ally McBeal co-stars began dating after he appeared on the show. They didn’t last long, which worked out just fine, as he is now married to producer Susan Levin and she’s with longtime beau Harrison Ford.

Robert Downey Jr and Calista Flockhart at the Golden Globe Awards

Photo by Kevin Mazur / WireImage / Getty Images

Demi Lovato and Ryan Phillippe

The pair had been dating for a few months, but things cooled down pretty quickly when Lovato learned that Phillippe was going to be a dad, again, with his ex-girlfriend Alexis Knapp. Lovato was just 18 at the time, so a divorced father of three who was also twice her age was probably not the right choice for her.

Ryan Phillippe posing on the red carpet / Demi Lovato on the red carpet

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Then, in 2017, the two were spotted together again. In fact, he was seen leaving her house in the wee hours of the night. Phillippe was 43 at the time, sneaking out of the 25-year-old pop star’s home at around 5 a.m.

Kaley Cuoco and Henry Cavill

These two had a summer fling in 2013. The star from The Man of Steel and the star of The Big Bang Theory together as a couple pretty much came out of nowhere. It’s almost like someone picked their names out of a hat.

Kaley Cuoco on the red carpet / Henry Cavill posing on the red carpet

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And it’s as though the randomness of their coupledom was the reason why it ended. Their relationship fizzled just about as quickly as it heated up. Within a week or two of announcing their relationship, the two were no longer an item. Go figure!

Lance Armstrong and Kate Hudson

These two started dating in 2008 and got serious. But it was a little too fast for Armstrong, who broke it off with the “needy” actress just three months later. They started dating after Hudson broke up with ex-boyfriend Owen Wilson for the second time.

Lance Armstrong and Kate Hudson having a drink and laughing together

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She and Armstrong were seen leaving their hotel in Monaco, France, to take a boat trip. They flaunted their new romance the whole weekend. It was very likely a blow to Wilson, who has, sadly, been reported to have attempted suicide. It’s unclear if it had anything to do with his split from Hudson, though.

Eva Longoria and JC Chasez

In 2005, the actress and former ‘N Sync star were briefly an item. She’s been said to have inspired some of his solo love tunes, too. When the Desperate Housewives star was spotted at Monterrey’s international airport with ‘Chasez, it sparked questions.

JC Chasez and Eva Longoria on the red carpet dressed up

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The two were apparently together for about eight months before calling it quits. Neither he nor she ever spoke about their relationship. But when they were together, they would go to red-carpet events and they attended the Emmy Awards in 2004. Now, Longoria is married to Jose Baston, whereas Chasez appears to be single.

Leonardo DiCaprio and Blake Lively

The 2011 fling between these two pretty people made for some gossipy goodness. The two never officially went public, but then again, when does DiCaprio ever go public with his love life? The two vacationed together in Italy and the French Riviera.

Leonardo DiCaprio on the red carpet at the Academy Awards / Black Lively dressed up on the streets of Manhattan

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They dated for five months. Eventually, Lively started dating, then married, and then had kids with Ryan Reynolds. As for DiCaprio? Well, sorry ladies, the bachelor is still, unbelievably, single. But that also means that he’s on the market! As Lloyd from Dumb and Dumber said: “So you’re saying there’s a chance.”

Josh Groban and January Jones

Before becoming a hot commodity on Mad Men, the actress dated the famous crooner and Rising Star host for three years. But they split up in 2006. He said that he was “madly in love” with the model turned actress.

January Jones and Josh Groban on the red carpet

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He also said that it was his longest relationship. “I’d love to get into another serious relationship. I am a real romantic at heart,” he added. Well, Josh, the sea is large and there are plenty of fish. Hollywood fish at that!