Some celebrity couples are iconic and were so influential on pop culture that they’ll never be forgotten. Everyone knows that Brad Pit and Angelina Jolie used to date, Khloe Kardashian dated Lamar Odom, Kylie Jenner dated Tyga, Selena Gomez went out with Justin Bieber and Britney Spears and Justin Timberlake used to be an item.
But what about celebrities lesser known relationships? Who did Selena date after Justin? Which star did Kim Kardashian date before Keeping Up With The Kardashians and the infamous sex tape came out? Who did Ariana Grande date before Mac Miller and Pete Davidson?
These odd celebrity couples are shocking but strangely accurate.
Check out the 50 strangest celebrity couples who you didn’t know dated below.
Joe Jonas & Gigi Hadid 2015
Before Gigi Hadid was a household name and dating Zayn Malik, she was dating Joe Jonas. The two only dated for five months but were friends for a few years before dating. Rumors that the two were dating began in 2014, but Hadid kept saying that they were just friends.
In a live video posted on September 2015, Hadid admitted that she first met Joe in 2010. “We met at the Grammys when I was 13 years old,” Hadid said. “And he asked me to a baseball game, and I said, ‘No.'”
Despite being turned down, Joe gave Hadid his number, and they remained friends until 2015 when they began dating. She even co-directed Joe’s band, DNCE’s music video for their song “Cake By The Ocean.”
Joe and Hadid tried to set up Kendall Jenner and Joe’s brother Nick, but it didn’t pan out.
The two broke up in November 2015, and according to People magazine’s source, the breakup wasn’t bad. The two just had conflicting work schedules, so they ended things.
Soon after they broke up, Hadid began dating Malik, which Joe thought was suspicious. He told The Mirror, “I think it’s interesting that she moved on so quickly, I mean it was definitely very quick.”
Ariana Grande & Big Sean 2014-2015
Ariana Grande and Big Sean began dating in August 2014. Big Sean said that at first he and Grande were just friends.
“We started out as friends, but that was the thing. It progressed from there, and that’s the first time I’ve ever been in a situation where we started as friends and it progresses, so that’s what it is,” he said.
Big Sean was featured on two of Grande’s tracks, “Right There” and “Best Mistake.”
Since confirming their relationship in October 2014, they posted many Instagrams of each other and attended numerous red carpets together.
After dating for eight months, the couple called it quits. Their respective busy schedules got int the way of their budding romance. Us Weekly reported that the two had an amicable breakup and their tour schedules were the cause of their breakup.
“They made the decision to part ways because their conflicting touring schedules would keep them apart over the next year,” a source told Us Weekly.
Despite the two musicians saying there were no hard feelings, TMZ reported that Grande ended things with Big Sean over a song lyric. She supposedly felt “humiliated” that Big Sean rapped about her “billion dollar p***y” on his track “Stay Down.”
Kylie Jenner & Jaden Smith 2013-2014
Rumors surfaced in 2013 that Kylie Jenner was dating Jaden Smith. The two teenagers never confirmed their romance, bt they were seen holding hands while out on a date at a movie theater.
“She’s one of my best friends,” Smith said about Kylie. “I was in L.A., we were all hanging out. Then I went to New York and she came too, then she came here and surprised me, so that’s pretty baller.”
Seems pretty extra that your friend would follow you to New York City to surprise you.
They never confirmed their relationship and rumors died down until the two were seen kissing in 2014. Smith went to Kim’s wedding to Kanye West with Kylie. At the reception, the two were seen making out.
The two are now just friends and still run in the same friendship circle.
Kim Kardashian & Nick Lachey 2006
Kim Kardashian and Nick Lachey briefly dated in 2006. Their relationship was cut short because Lachey believed Kim was dating him to gain attention. If only they could fast forward to now and see how famous Lachey is now compared to Kim. But 2006 was a different time for the Kardashian family, their show Keeping Up With The Kardashians wasn’t even on the air yet! They dated pre-KUWTK and even pre-sex tape scandal.
The two met at a party NFL quarterback Matt Leinart was hosting. Kim and Lachey dated after his divorce with Jessica Simpson. When Lachey was asked if Kim dating him was the start of her career, he responded, “That’s one way to interpret it.”
He then went on to suggest that Kim would call the paparazzi on them. He recalled there were multiple times that the couple wasn’t being followed, but then all of the sudden paps would show up.
“Let’s just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside,” Lachey recalled.
In Kim’s book Kardashian Konfidential, she credited her relationship with Lachey as what caused the paparazzi to start following her around.
They called it quits shortly after they began dating.
Rihanna & Shia LaBeouf 2007
Rihanna and Shia LaBeouf went out on a date in 2007. The two were photographed out to dinner in Beverly Hills in 2007, which sparked dating rumors. LaBeouf later confirmed that the two were on a date to Playboy in 2009.
LaBeouf said that Rihanna reached out to him through text first. The two decided to go out, but it didn’t become anything more than a date.
“It never got beyond one date,” he said. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”
Rihanna has never talked about their date, but she’s a busy lady running an empire.
Niall Horan & Selena Gomez 2015-2016
Niall Horan and Selena Gomez sparked dating rumors in late 2015 when the two were supposedly caught on a date. Then the two attended Jenna Dewan’s birthday party together and were spotted packing on the PDA.
“Selena and Niall came together and were seen kissing,” an eyewitness told E! News. “They tried their best to keep to themselves in their private booth behind the DJ table in the main room but that was not happening. They were seen making out by a handful of people. Selena seemed super into it. And Niall even more so.”
A few months later in February 2016, it was reported that the couple was on the rocks. Gomez just wanted a fling, she recently broke up with Justin Bieber the first time around, and Horan wanted something more. They ended things and remained friends.
John Mayer & Jessica Simpson 2006-2007
John Mayer and Jessica Simpson dated from 2006 to 2007 and Mayer revealed a lot about their relationship. In a 2010 issue of Playboy, Mayer went into detail about his relationships, specifically with Simpson. He called Simpson “a drug” to him.
“And drugs aren’t good for you if you do lots of them,” Mayer said. “Yeah, that girl is like crack cocaine to me.”
“Sexually it was crazy. That’s all I’ll say,” the singer continued. “It was like napalm, sexual napalm. Did you ever say, ‘I want to quit my life and just f***ing snot you? If you charged me $10,000 to f**k you, I would start selling all my s**t just to keep f***ing you.'”
Simpson was less than happy about Mayer’s comments about their sex life. She went on The Oprah Winfrey Show and talked about how much the comments hurt her and how she isn’t over it despite Mayer apologizing.
Zoe Kravitz & Drake 2013
Zoe Kravitz was most famously linked to rapper Drake in late 2013 after the duo was spotted together at multiple events, including a Beyonce concert where they were seen making out in December of that year. While they never officially announced that they were an item, the musicians posted a series of flirtatious tweets addressing each other, as well as pictures with and of each other on Instagram.
Zoe Kravitz on Californication…my two favorite things in the world. But she's not a thing…she's everything.
— Drizzy (@Drake) January 30, 2011
Fast forward to 2017, Kravitz went on Andy Cohen’s Watch What Happens Live! and asked Kravitz about the relationship. A viewer called in and asked Kravitz if she ever dated Drake. “We hung out for a minute,” she responded. “But we are very good friends, you know.”
Cohen pressed for more and Kravitz coyly said that they just “hung out a little bit.”
Nick Jonas & Olivia Culpo 2013-2015
Nick Jonas and Olivia Culpo met while he hosted and performed at Miss USA back in 2013. Culpo previously won Miss USA in 2012 and then Miss Universe in 2012. The two hit it off and began dating and attending red carpets together and making out in public.
“We went out one night and this guy was looking at her for a little too long,” he said. “It was uncomfortable. I’m not a jealous person and this was an experience that I was one of two drinks in. I really got into it and then I decided to let me just process this a different way and go into the studio write this song.”
Nick performed during the 2014 Miss Universe pageant and even hopped off stage to sing directly to Culpo. Many thought he was going to propose to Culpo because he dropped down to one knee while singing to her.
The two don’t have any hard feelings now and have both moved on.
Olivia Munn & Justin Timberlake 2010
It was rumored that Justin Timberlake cheated on his then-girlfriend Jessica Biel with Olivia Munn. In 2010 Us Weekly reported that Munn and Timberlake had a three-day fling that was passionate and not kosher.
Their source said the two met at a MySpace event and they exchanged numbers. From there, Timberlake was on a mission and “started chasing her immediately.” Munn rejected his advances believing he was still with Biel. Timberlake supposedly lies and told her that he and Biel were over.
Believing that Timberlake was single and ready to mingle, Munn took him back to her hotel room where the two stayed for two days. When she found out that Timberlake and Biel were still together, she broke it off.
In January 2011 Life & Style reported that Timberlake tried to rekindle his romance with Munn through text, but she ghosted him.
Channing Tatum & Amanda Bynes 2006
Channing Tatum and Amanda Bynes were more than co-stars while filming She’s The Man. The two were photographed kissing while on the set of She’s The Man when the cameras weren’t rolling. Not only did this spark dating rumors, but it also started cheating rumors because Tatum was supposedly still with Jenna Dewan.
Not only were they photographed making out in broad daylight but they were seen walking with his arm around her shoulder and her hand on his washboard abs. When the two were doing press for the movie, they were extra flirty. While at Fuse, Tatum called Bynes “so hot.”
They never confirmed if they were together, but a photo says a thousand words.
Rita Ora & Rob Kardashian 2012
It’s okay if you don’t remember that Rob Kardashian and Rita Ora dated. It was before Ora was a breakout singer and the Kardashians weren’t bonafide celebrities yet. The two were rumored to be dating in May 2012, when they were seen together at Kanye West and Jay-Z‘s London show together. They denied their relationship.
They finally confirmed they were an item in October. But their relationship crashed and burned when Rob accused Ora of cheating on him with 20 guys.
“She cheated on me with nearly 20 dudes while we were together,” Rob tweeted in December 2012. “How can a woman who is so busy trying to start her own career have time to be with so many dudes all while in a relationship?!”
Rob eventually deleted the tweets, but then a few hours later posted more tweets accusing Ora of cheating on him with multiple men.
In March 2013 Ora told an Australian magazine she never thought she and Rob were exclusive and denied cheating.
“I never thought it was actually a relationship, in all honesty,” Ora claimed. “I never mentally defined it as ‘boyfriend, girlfriend.’ When I split up with him, I said, ‘It’s because I’m never there, I don’t know how to do it.’ That’s all I said, then…the rest happened. he obviously felt that creating myths was the way forward.”
Later on Kourtney and Kim Take Miami, Rob admitted that he tweeted those awful things to push Ora away because he kept taking her back. In 2018 Rob retweeted Ora’s tweet explaining and apologizing for her song “Girls.”
Hailey Baldwin & Chris Brown 2015
Hailey Baldwin was spotted hooking up with Chris Brown while the two both attended the Cannes Film Festival in 2015. The two met thanks to Kendall Jenner and Justin Bieber. The foursome would hang out and go on double dates all the time in 2014. Kendall, Baldwin and Beiber even flew out to Washington to attend one of Brown’s concerts.
Then in 2015 Brown performed at Cannes and Baldwin, along with Kendall and Bella Hadid, went to his concert. The two were supposedly looking like a couple all weekend, but they never confirmed their relationship.
Baldwin claims that the two did not date, but they seemed to be a little too cozy to be just friends. The two didn’t last, and Baldwin went on to get engaged to Bieber in 2018.
Chris Evans & Jessica Biel 2001- 2006
Chris Evans and Jessica Biel dated before they were wildly famous. The celebrity couple was strong for five years before calling it quits. They began dating way before Evans was Captain America and right after 7th Heaven ended for Biel.
It’s unsure how the couple met, but in 2001 they began going to red carpets together and packing on the PDA. Then in 2004, they starred in Cellular together playing boyfriend and girlfriend.
In a 2005 Cosmopolitan interview, Biel talked about Evans and the cute things he did for her 21st birthday.
“When I turned 21, I actually awoke to find my bed covered in rose petals,” Biel told the magazine. “In the middle of the night, he had pulled apart at least 24 roses in all different colors and sprinkled the petals everywhere. He’s definitely a keeper.”
Biel even said that the couple had discussed marriage and kids. “We always talk about it,” she said. “We both want to be married, and we both want to have children.”
Then in 2006, the couple starred in London together but sadly broke up a few months after the premiere. It’s unsure why the couple called it quits.
Taraji P. Henson & Lamar Odom 2008-2009
Before Lamar Odom and Khloe Kardashian got hitched, he was dating Taraji P. Henson. No seriously, they were dating right before Odom and Khloe got together. The two began dating in late 2008, and according to Bossip, they went to HBO’s Golden Globe after party and a Grammys after party together.
Former Los Angeles Lakers radio host, Matt “Money” Smith revealed that Odom proposed to Henson a week before meeting Khloe and getting hitched to her a month later. He said, “[Lamar] was madly in love with another young lady [Taraji] no less than one week before he met Khloe and asked that young lady to marry him and she said, ‘Whoa, slow down.'”
The two ended things after Odom popped the question and he moved on very fast. Odom met Khloe a week later, and they got hitched a month later in September 2009.
Scott Disick & Bella Thorne 2017
After Scott Disick‘s and ex-partner and mother to his kids, Kourtney Kardashian began dating other people Disick decided to do so too. Except the only difference is that Disick jumped from young model to young actress rapidly all while threatening Kourtney’s then-boyfriend Younes Bendjima. One of the young celebs that Disick courted was Bella Thorne.
Disick and Thorne’s relationship was short-lived but made an impact. The Kardashian family dissed Disick and Thorne on their show Keeping Up With The Kardashians with Kim Kardashian calling the couple “desperate.”
“They looked so desperate at the airport,” Kim said about the couple publicly heading to Cannes together. “Who goes to LAX together? It’s not a good look for Scott.”
Later on KUWTK, Kendall Jenner said that Disick was only hanging out with Thorne to make Kourtney jealous. A few months after the couple broke up Thorne admitted having never been intimate with Disick.
“I was never with him sexually,” Thorne told Jenny McCarthy during her podcast. “I’m very friendly with Kylie and Kendall. Kylie and I used to be very close.”
She went on to say that the Kardashians used their relationship for views on their show. Yikes.
Blake Lively & Leonardo DiCaprio 2011
Blake Lively met Leonardo DiCaprio when she auditioned for Daisy Buchanan in The Great Gatsby, which was opposite of DiCaprio’s character. She didn’t snag the role, but she snagged DiCaprio. The two dated for roughly five months. They were each other’s rebounds, Lively just broke up with Ryan Gosling and DiCaprio and Bar Refaeli just ended things.
They made their relationship official when they went to the Cannes film festival together in 2011, this was a few months after their The Great Gatsby meet cute. After Cannes, the two jet-setted to Portofino, Italy and spent the weekend there. Their five-month fling was far from low-key. After their European vacation, they went to Disneyland together and they were seen hanging out in Santa Barbara, New York City and Australia.
Lively was still filming Gossip Girl and to keep their romance alive she had a “flat Stanley” doll that she would take pictures with and send to DiCaprio. The executive producer of the show, Joshua Safran told Vanity Fair, “We learned a lot from Blake. When I think about shooting the L.A. episodes, Blake was dating [DiCaprio] at the time, and she had this thing where had a doll that she took photos of that she sent to Leo.”
Their whirlwind romance ended in October 2011 when Lively began seeing Ryan Reynolds.
Timothée Chalamet & Lourdes Leon 2013
Timothée Chalamet and Lourdes Leon dated for a brief time in 2013. The two were both students at La Guardia High School of Music & Arts & Performing Arts at the time. Chalamet was in the grade above Leon. The tabloids loved their relationship because Leon is the daughter of Madonna and Chalamet was an up and coming actor who was starring in Homeland at the time.
In 2017, Andy Cohen asked Chalamet about his romance with Leon and the first time he met Cohen. The two met at a party with Leon and Madonna. “That was actually a really fun night,” Chalamet told Cohen.
“Well I don’t know if you remember but Madonna was kinda with us dancing and my buddy Joey was there and Lola was there too and we were all dancing together,” he went on, “I don’t know I usually don’t talk about this stuff, but that was a good night.”
Chalamet didn’t go into details on how long he dated Leon, but they supposedly were only together for a few months.
Lana Del Rey & G-Eazy 2017
The two sparked dating rumors when they spent Coachella weekend together. Lana was supposed to be on G-Eazy’s “Him and I” track, but then they broke up, so he axed her from the song.
“G-Eazy initially begged Lana to be the singer on his new song “Him and I” but then they split, and he changed his mind,” a source told Sunday Mirror.
Instead, G-Eazy asked Halsey to be on the duet, and the two started dating quickly afterward. Lana wrote the song “White Mustang” about G-Eazy and at a show, she switched up the lyrics and totally shaded him. During a show in January 2018, she switched the lyric, “Couldn’t stop the way I was feeling the day your record dropped,” to say “his record” and then added, “and it wasn’t even that good!”
Amy Poehler & John Stamos 2012
Yup, Leslie Knope and Uncle Jesse went out. While out promoting her memoir, Yes Please, Poehler revealed to Howard Stern that she went out with John Stamos. After separating from Will Arnett in 2012, Poehler re-entered the dating world. She went out to dinner with Stamos but only realized halfway through that it was a date.
“I remember I was at dinner with John Stamos. I think if you just are around him you are…handsome men are really something else. First of all, they’re so handsome,” Poehler said. “We were having dinner and I was like, ‘Oh, maybe this is a date!'”
If it was a date or not, it doesn’t matter because Poehler said she “blew it.” Later on, Stamos confirmed that it was a date!
“We’re really good friends,” Stamos told Extra. “I guess [Amy] didn’t know it was a date. I asked her out on a date…and we had a really nice time. Then I hear she thought it wasn’t a date. it was a date in my eyes.”
Sarah Jessica Parker & Robert Downey Jr. 1984-1991
Sarah Jessica Parker and Robert Downey Jr. dated for a long time, seven years, but many forget that they were a couple.
The couple met when they were 18, way before Sex and The City and Iron Man. The two met on the set of Firstborn and moved in two weeks after dating. What was the downfall of their seven-year romance? Downey’s drug addiction. In a 2008 interview with Parade, Downey admitted that drugs and alcohol were the cause of their breakup.
“I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica, because it is the furthest thing from what she is,” Downey said. “She tried to help me. She was so miffed when I didn’t get my act together.”
Parker said that she didn’t even know Downey was an addict for a long time. She told People that their relationship was a turning point for herself.
“I learned how to take of myself,” she said. “There was a huge amount of time spent making sure he was okay. At a certain point, I had the courage to say ‘I’m going to walk away and I’m just going to pray that you don’t die.'”
Parker concluded by saying she doesn’t regret or resent her time spent with Downey. He eventually got sober in 2002. The two have since gotten closure and reconnected over dinner in 2016.
Cher & Tom Cruise 1985
Cher and Tom Cruise used to date in the 80s unknown to just about everyone.
In a 2018 tell-all interview with the Mail on Sunday, Cher opened up about how she met Cruise. According to Cher, the two met in 1985 at Sean Penn and Madonna’s wedding. They then ran into each other again at a White House even and clicked.
“A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic,” she said. “We didn’t go out till way later, but there definitely was a connection there.”
While on Andy Cohen’s Watch What Happens Live! Cher admitted that Cruise was top five on her list of Best Past Lovers. When Cohen asked the singer who was the best lover she ever had, Cher responded, “A lot of them kind of came in first. I’ve just had the greatest lovers ever.”
When specifically asked where Cruise falls on the list Cher admitted he’s top five, but wouldn’t say what specific number. “It’s not a long list, just a good list,” she added.
Cher also added that their relationship was “hot and heavy.” Oh man.
George Clooney & Carole Radziwell Late 1990s
Former Real Housewives of New York City star Carole Radziwell spilled the tea and told her cast members that she used to date George Clooney. The two dated either in the late 1990s or early 2000s. Radsizwell who wasn’t sure of the timeline said in an episode that they dated “Post-Dr. Doug Ross” but “Pre-Danny Ocean.” She also rated him a nine out of 10 in bed.
Clooney has never spoken about their relationship and there aren’t photos of the two together. It seems that Radziwell and Clooney had a quick fling.
Ellie Goulding & Prince Harry 2016
Before there was Meghan Markle, Prince Harry was rumored to be dating British singer Ellie Goulding. The pair met thanks to his brother Prince William and sister-in-law Kate Middleton. The royal couple invited Goulding to sing at their wedding reception in 2011. The two linked up three years later in 2014 at the Invictus Games, but rumors didn’t start until 2016.
In June 2016 the two both attended the Audi Polo Challenge and were seen kissing and being all over each other. A source told The Sun, “[Harry] has told friends how much he likes Ellie and she is clearly taken by him.”
The source said that the polo after party was crazy and there was a strict no phone policy.
“Harry was really going for it after the polo – he was drinking and dancing,” the insider said. “They were part of a wider group including Tom Hardy. But Harry and Ellie only had eyes for each other all night – they spent a lot of time sitting together under blankets. They were seen kissing before Harry had to go because he was playing polo the next day. Ellie left about five minutes later.”
Britney Spears & Jared Leto 2003
Britney Spears and Jared Leto were rumored to have dated in 2003. This is a classic case of “our exes are dating so let’s date.” Spears and Leto’s romance rumors started right after Leto’s ex-fiancé Cameron Diaz and Spears’ ex-boyfriend Justin Timberlake behind seeing each other. The media dubbed them a revenge couple.
They were spotted eating dinner out in Los Angeles and then attending Ben Affleck‘s birthday party together.
“She was out for a girls’ night out,” Spears’ spokesperson said. “One of her friends knew Jared, who was there with friends, and both groups got together and had a good time.” The two decided to ditch their friends and head to Affleck’s party arm-in-arm.
Spears claims the two were just “really good friends,” so you can be the judge if they actually dated or not.
Henry Cavill & Kaley Cuoco 2013
Kaley Cuoco managed to keep a two-year relationship with her Big Bang Theory co-worker Johnny Galecki quiet until they broke up. But she couldn’t manage to keep her short fling with Henry Cavill under wraps at all.
The two only dated for 12 days but managed to be photographed and talked about endlessly for those 12 days.
“I had no one following me until I met Superman,” Cuoco said about her fling with Cavill. “I’ve been in this business for 20 years, and my whole life, I could go anywhere, do anything. There has not been one paparazzi photo of me until like several months ago. The recognition was crazy.”
Their short fling has been accused of being fake considering the two shared a publicist at the time. Their 12-day romance has been dubbed fake and just meant to help both of their careers.
Sandra Bullock & Matthew McConaughey 1996-1998
Sandra Bullock and fellow actor Matthew McConaughey met on the set of the legal thriller A Time To Kill, where they were co-stars, and dated for two years afterward. Bullock seemed rather insistent that although there was “fabulous chemistry” between them and that he had become a”powerful force in [her] life,” the two were really better as platonic friends.
In 1997, while promoting Hope Floats, Bullock went on Oprah where she was asked about her rumored boyfriend McConaughey. When asked point blank if she was dating McConaughey she responded, “No, we are not,” but then added, “whatever woman gets him is going to have to get by me.”
But then in a 2003 interview with Cosmopolitan, Bullock admitted to technically dating McConaughey. Cosmopolitan pointed out that when asked if she was dating McConaughey she always said they were “friends” but never said they were just friends.
Sandra responded, “If you were to add the word just, it would probably be a bit of a lie. So I’d say we’re friends.”
The two are just friends now and remain friends.
Dakota Johnson & Benedict Cumberbatch 2014
Back in 2014 rumors started that Dakota Johnson and Benedict Cumberbatch had a quick fling. The two met at the Met Gala 2014 and started hanging out the next day. They were spotted going to lunch together with another mystery blonde. The couple goofed around and put paper napkins on their faces while getting snapped by the paparazzi.
At the time it was believed Cumberbatch had a secret girlfriend, then he was spotted with Johnson. They were all laughs and smiles during lunch making fans believe it was a date. They never confirmed or denied their romance, if anything it was a quick relationship.
Scarlett Johansson & Jared Leto 2004-2005
Scarlett Johansson and Jared Leto had a brief fling between 2004 and 2005. They were first spotted together in Los Angeles, but never publicly discussed their relationship. They were photographed together all the time throughout 2004 and 2005 and pictured making out.
In 2004 the couple even went to Cape Town, South Africa together. They were photographed at a cafe and signed autographs for a few fans. Leto was in Cape Town to film Lord Of War and Johansson flew down to visit him.
The two dated on-and-off for a year before the public appearances ceased. They were photographed in 2012 hanging out at the Democratic National Convention and looked friendly.
Kate Hudson & Dax Shepard 2007
Kate Hudson and Dax Shepard’s relationship started quickly and ended even quicker. The two actors got together in July 2007 but their relationship only lasted a few months before they broke up.
The couple never publicly acknowledged their relationship but they were photographed cuddling and making out. Supposedly Hudson is the woman who broke up Shepard and his then-girlfriend Kristen Bell.
In 2017 Bell told PopSugar that she and Shepard broke up before they got serious and eventually married. “We were dating for about three months, and I already knew that I was in love with him and he was hesitant because he knew he was still dating other people,” Bell said.
“He sat me down and said, ‘I can’t have this right now. I think you’re wonderful, but I am still dating other people,'” Bell recounted. “And then I, like, liquefied and fell to the ground, but I felt incredibly respected that he had the balls to tell me weren’t in the same place.”
A few days later Shephard called Bell and told her he made a mistake and said, “‘I don’t know what I was thinking. I was dating someone else but they’re just not as interesting as you, and I don’t know what I’m doing.'”
Based on Dax’s relationship timeline it’s believed that the other woman he was dating was Hudson.
Macaulay Culkin & Mila Kunis 2002-2011
Macaulay Culkin and Mila Kunis dated for eight years but kept their relationship and dramatic breakup under wraps. The two dated from 2002 to 2011 when Culkin was retired from acting and Kunis was becoming the star she is today. They dated each other throughout their 20s.
Kunis told Women’s Health in 2009, “We grew up together. You find a steady rock in your life and that’s all you need. We have our ups and downs, but work through them.”
The two ended their eight-year relationship right before Black Swan came out. At first, they released a statement saying the split was amicable. But years later on Dax Shepard’s podcast, Kunis admitted that she “f**ked up” and that she did something messed up that ended their relationship.
“And it’s f**ked up what I did. It’s f**ked up what I did and it’s f**ked up how I did it. When I got to be single I said, ‘I just need to figure myself out.’ I genuinely need to know why I did what I did, and, like, regroup myself as a human being.”
Kunis never divulged what she did to end their breakup.
Ashton Kutcher & January Jones 1998-2001
Ashton Kutcher dated January Jones before she was wildly famous for her role as Betty Draper in Mad Men. There aren’t many details about their three-year relationship, but supposedly Kutcher wasn’t supportive of Jones becoming an actor.
In a 2009 GQ interview, she said that her first boyfriend in Los Angeles, not naming names, was less than supportive of her becoming an actress.
“[He] was not supportive of my acting,” Jones told GQ. “He was like, I don’t think you’re going to be good at this. So f**k you! He only has nice things to say now—if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.”
Even though Jones didn’t confirm that was about Kutcher, it was believed to be about him based on the years they dated. When asked about the quote in 2016 on Andy Cohen’s Watch What Happens Live! Jones skirted around that question. She simply said she hasn’t talked to Kutcher since they broke up but wish him and his family well.
Shia LaBeouf & Carey Mulligan 2009-2010
Carey Mulligan and Shia LaBeouf sparked dating rumors in 2009 when they were seen kissing at a restaurant in New York City. The two co-starred in Wall Street: Money Never Sleeps and dated for roughly a year.
LaBeouf claims to have been the one to end their relationship. He said that they just had different lifestyles and they both wanted different things. Mulligan wanted to get married, have kids and settle down while LaBeouf wasn’t ready to do so.
“Carey is not just an actress, she is a great human being, a sweet girl and super intelligent,” LaBeouf said. “Our thing came down to not having compatible work/lifestyles. We were always traveling and has sensibility differences that weren’t conducive to living with one another. I’m harder on myself and my surroundings than she is, and we had a culture shock in terms of meeting her parents and vice versa.”
Brad Pitt & Thandie Newton 1994-1995
Brad Pitt and Thandie Newton were co-stars in Interview With A Vampire and began dating soon afterward. Pitt has described filming Interview With A Vampire as an awful experience, but it couldn’t have been too awful because he and Newton hit it off. Newton had a small role in the film as Yvette one of the servant’s to Pitt’s character.
The two actors only dated for a year before breaking up. There are not a lot of details of their relationship or why they split up, but supposedly there were no hard feelings during the breakup. The two still claim to be friends.
Zoe Kravitz & Michael Fassbender 2010-2011
Michael Fassbender and Zoe Kravitz dated for less than a year before calling it quits. The two met on the set of X-Men: First Class and despite their 12-year age gap hit it off.
They didn’t announce their relationship until the movie came out. But after filming the Marvel movie, they hung out in NYC and packed on the PDA. “They’re really low-key, but have a great time together just talking music or movies,” a source told Us Weekly. “They really didn’t want to be a topic of conversation during the press for X-Men.”
As for their 12 year age gap, the course said that “Zoe’s really mature for her age in that she has very strong opinions and she is very confident in herself. Most people are shocked to learn she’s so young; she doesn’t really bring it up and age would never stop her from dating anybody.”
The two broke up little less than a year late but remain friends.
Chelsea Handler & 50 Cent 2010
Rapper 50 Cent and funny woman Chelsea Handler “casually dated” for a while. The two sparked dating rumors when they were seen at dinner together in New Orleans in 2010. The two were very coy about their relationship and didn’t confirm they dated until after they broke up.
Before they were spotted getting dinner in NOLA the two were flirty on her show, Chelsea Lately and in interviews. The two remained flirty throughout 2010 saying nothing but positive things about one another, posting snaps together and leading fans to believe they were together.
It wasn’t until a year later in 2011 that Handler confirmed that she and 50 Cent “casually” dated. “He’s a very sweet, nice guy, ” Handler told Piers Morgan. “I was sampling, kind of, the atmosphere, seeing what was out there, and I was satiated.”
Despite breaking up the two remain friends. In 2014 50 Cent celebrated Handler’s birthday by sharing a topless photo of her on his Instagram. How cute!
John Mayer & Jennifer Aniston 2008-2009
John Mayer and Jennifer Aniston dated on and off for a year from 2008 to 2009. Even though their relationship only last a year it was very intense.
After they broke up, Mayer told Playboy in 2010 that their relationship was “deep” and “intense.”
“We just have a regard for each other’s feelings that is pretty intense,” he said. “It’s been a deep relationship, and it’s no longer taking place at all. Have you ever loved somebody, loved her completely but had to end the relationship for life reasons?”
He later told Rolling Stone in 2010 that he “never really gotten over it” and that their breakup was “one of the worst times of my life.” Mayer also said that something he did ended their relationship.
Apparently, there is still bad blood between the exes. In Andy Cohen’s book Superficial, he revealed that he was with Mayer when they ran into Aniston in 2016, and it did not end well. They were out for drinks at the Sunset Tower when they spotted Aniston there with her former Friends co-stars Courtney Cox and Lisa Kudrow. Cohen wanted to go over an say hi, but Mayer refused and said it would not end well.
Seth MacFarlane & Emilia Clarke 2012-2013
Game of Thrones star Emilia Clarke and Family Guy creator Seth MacFarlane dated for a year but kept their relationship under wraps. They were seen at an HBO party together, which sparked dating rumors, but otherwise, they kept a low profile.
It wasn’t until 2016, three years after they broke up, that Clarke opened up about her romance with MacFarlane and what it was like to date someone else famous.
During an interview with Glamour, Clarke was asked what a con was about dating something uber famous. Clarke said, “Well, a con is you have stranger giving you love-life advice like, ‘I’m a big fan of the show, and I’m not sure what you’re doing with this guy,’ which I didn’t react well to. 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.”
The two supposedly broke up because of long distance and scheduling conflicts. The two exes have nothing but nice things to say about each other, so it seems they ended things amicably.
Evan Rachel Wood & Marilyn Manson 2007-2011
Westworld actress Evan Rachel Wood and musician Marilyn Manson dated for four years and at one point were engaged before they broke up. The two met at a party in Los Angeles in 2006 when she was just 18 years old. Wood and Manson, who was 36 at the time, began dating despite Manson still being technically married to Dita Von Teese. Manson’s divorce to Von Teese was finalized in December 2007.
Their relationship was scrutinized for their age difference, and the controversial music video Wood starred in. Wood played a Lolita-esque character in Manson’s 2007 music video for “Heart-Shaped Glasses.” There were rumors that the sex scenes in the music video were real, Wood denies it, but Manson pleads the fifth.
They dated on and off from 2007 to 2010 and eventually got engaged in 2010. Manson popped the question while on stage in Paris. But they broke things off in 2011 and never made it to the altar.
Ryan Reynolds & Alanis Morissette 2002-2007
In 2002 Alanis Morrissette and Ryan Reynolds began dating. The two met at Drew Barrymore’s birthday party and hit it off. The two were going so strong that Reynolds even proposed to the singer in 2004. The two got engaged right before she went on the 10th-anniversary tour of her album Jagged Little Pill.
“He’s just such a supportive creature,” Morissette said in 2005. “I feel so loved by him, in a trampoline kind of way. He’s always very happy for me.”
The two remained engaged for three years before calling it quits. They never got married. A few months later Reynolds moved on to Scarlett Johansson and they got married in 2008. After he divorced Johansson, he moved on with Blake Lively soon after and they quickly got married.
Morissette confirmed that her 2008 album Flavors of Entanglement was about her relationship and breakup with Reynolds. The song “Torch” specifically is about grieving after a breakup.
Lenny Kravitz & Nicole Kidman 2002-2003
Many people don’t’ know that in between Nicole Kidman’s divorce from Tom Cruise and marriage to Keith Urban she was engaged to Lenny Kravitz. Kidman admitted in a 2007 interview with Vanity Fair that she was engaged in the early 00s, but wouldn’t say to who. The actress just said the timing was right between the two former fiancés.
Then in a 2017 interview with The EDIT Kidman revealed that the man she was engaged to Lenny. In the interview, she divulged that she and her Big Little Lies co-star Zoe Kravitz already had a relationship because hello, she was engaged to her father.
“Well, I knew Zoe because I was engaged to her father. It’s all in the family! I love Lenny; he’s a great guy.”
Later on, Zoe did an interview with The EDIT where she talked more about her relationship with Kidman and her engagement to Lenny.
“I think she forgot that no one knew that,” Zoe said about Kidman revealing the engagement. “I hadn’t seen her in a long time before Big Little Lies, but there was a point where we were all kind of living together. I was about 13, and she would take me to see movies; she was so nice to me.”
Despite being broken up, the two are still friends and even hung out at the 2016 CMT Music Awards together with Urban.
Eric Andre & Rosario Dawson 2016-2017
When Eric Andre and Rosario Dawson began dating no one could believe it. Andre, known for his outlandish and hilarious comedy, started posting photos of he and Dawson making out on his Instagram and everyone wondered if it was a bit or real.
Even Chance The Rapper had to text Rosario and ask if she was actually dating Andre.
“He started posting more pictures of like our tongues touching and stuff, like personal pictures,” Dawson told Stephen Colbert in 2017. “I was like, ‘you’re a millennial man. You don’t post the tongue pictures!'”
While they were dating, Dawson had to have emergency surgery to have a cyst removed from one of her ovaries. She said that Andre took care of her while she was wearing a diaper. On the one year anniversary of her surgery, she posted a throwback of her and Andre in the hospital.
“It was the first time I told [Eric Andre] that I loved him (and very much not the last). Thankful for his care and all of the doctors and nurses and staff at the Desert Regional Medical Center.”
The two split in November 2017 after a year of dating.
Jack Antonoff & Scarlett Johansson 2002
Before they were famous Jack Antonoff and Scarlett Johansson dated and even went to prom together. The two both attended the Profesional Children’s School on the Upper West Side in New York City.
“When we were in high school, Jack was absolutely obsessed with her, and she broke his heart,” a fellow student told The Post. “They broke up shortly after graduation…She got swept up in the Hollywood scene.”
Antonoff’s ex-girlfriend Lenda Dunham found out about his dating history through Tumblr.
“The craziest thing that ever happen[ed] to me, was like, Old Loves is my passion, I check it, like, once a week,” Dunham said about the Tumblr page in 2014. “It’s how I kick back on a Friday night is to see what Old Loves has done. And I was going through it and I saw my boyfriend and his girlfriend from high school. Scarlett Johansson.”
“I’m not jealous,” Dunham clarified. “It’s very sweet. I love looking at pictures of them. She’s beautiful, he’s beautiful, but it was just so surreal to be looking through this blog that gives me so much pleasure and then there’s my boyfriend. And I was like, ‘My mind is going to explode.'”
Madonna & Dennis Rodman 1994
Unless you were born before 1994, you probably didn’t know that Madonna and Dennis Rodman dated. The two were only together for two months, but their relationship made waves. NBA fans accused their relationship a distraction for Rodman during the 1994 NBA Playoffs. The two broke it off after a few months because it just wasn’t working. They both wanted different things.
“Madonna wanted to have my babies,” Rodman said according to Huffington Post. “One time I was in Las Vegas at the craps table doing my thing when I got this frantic call. It was like the ‘somebody died call’ from New York. I picked up the phone and Madonna was like, ‘I’m ovulating, I’m ovulating. Get your a** up here.'”
Supposedly Madonna wanted to get pregnant so badly she banned Rodman from using condoms. He also admitted that he never gave Madonna oral sex, but later said it was a big part of his sex life.
The two were both huge characters who just couldn’t work it out.
Katy Perry & Russell Brand 2009-2011
When Katy Perry‘s and Russell Brand’s respective careers began to take off, they started to go out and eventually got married. In 2009 the two met on the set of Get Him to the Greek. Perry had a scene with Brand, but it was ultimately cut from the movie. They reconnected at the 2009 MTV VMAs and began dating in September 2009. A few months later, on New Year’s Eve 2009 they got engaged.
The couple wed on October 2010 in a Hindu ceremony in India. They didn’t last long because Brand filed for divorce after 14 months of marriage in December 2011. He allegedly told Perry he wanted a divorce over text. Right after they broke up, Brand called their marriage and Perry “vapid” and “vacuous” in his documentary.
Six years after their divorce, Brand said that fam and “living in those conditions” is what caused their split. Perry said she hadn’t heard from Brand since he split from her through text.
Drew Barrymore & Christian Bale 1990s
When Christian Bale and Drew Barrymore were only teenagers the two stars went out on a date. Nobody knew that the two actors went out until Bale admitted to their short fling in 2012.
Bale told GQ that he and Barrymore went to go see a movie, but it didn’t go much farther than that.
“We went to see some bloody awful horror film, and that was the end of it,” he recalled. “She never called again.”
Bale didn’t give any other details about their short fling, like how the two met and how old they were when they went out. All we know is that they were both teenagers, so it’s most likely they went out in the 90s.
Even though it didn’t work out for these two their love lives prevailed. Bale wen ton to marry Sibi Blazic in 200 and have two children.
Barrymore got married and divorced three times and had two children with her ex-husband Will Kopelman.
Fergie & Justin Timberlake 1997
Back during Justin Timberlake’s ‘N Sync days he and Fergie had a fling. They dated before his media-frenzy romance with Britney Spears. Timberlake was only 16 and Fergie was 23 at the time.
Not much is known about their fling, but Fergie has dropped a few insights on their quick fling. In a 2006 interview with Cosmopolitan, she said, “One of my good friends was dating JC Chasez, and so. We’d all hang out with ‘N Sync. Justin and I. would go out together and have fun and make out. We went to Hawaii together, but we were never serious. He was Mr. Right Now.”
In 2017 while on Andy Cohen’s Watch What Happens Live! the singer had to play Plead the Fifth. During the game, Cohen asked Fergie what was the “best and worst part” of dating Timberlake. She reiterated that “it wasn’t all that serious” and she and Timberlake were just a fling.
Pink & Joey Fatone 2000s
Back in 2000 when Pink went on tour with ‘N Sync and opened for the boy band, she had a secret relationship with Joey Fatone.
“Joey Fatone was in love with me,” Pink told Glamour in 2013. “He took me to Friendly’s on a date and he bought me an icecream. Such a sweetheart. He asked my dad’s permission!”
Their romance was short-lived and never played out. The two parted ways and ended up marrying other people. Pink married Cary Hart and has two children with him, Willow Sage and Jameson Moon.
Pink and Hart met in 2001 and briefly broke up but ultimately got back together. Then in 2005, she proposed to him and they got married in 2006. They separated for two years from 2008 to 2010 but eventually got back together.
Fatone married his wife, Kelly Baldwin in 2004. The two dated on and off for 10 years before getting hitched. They have two daughters together, Briahna and Kloey.
Janet Jackson & Matthew McConaughey 2002
Matthew McConaughey and Janet Jackson had a quick fling in 2002. The two met at the 2002 Grammys and hit it off. They posed for some backstage photos and ended up flirting all night long.
Star magazine reported that McConaughey was seen leaving Jackson’s Bel Air home the next morning and he supposedly spent the night. He was walking out of the mansion shirtless, carrying his shoes and whistling.
Despite the suspicious scene of him walking out of Jackson’s house shirtless and whistling, McConaughey denies that anything happened. “I met her at the Grammys and found her to be a very very sweet lady,” he said. We swapped some good music and she’s a dear lady. She’s a sweetheart but we’re not dating, we’re just friends. That’s about all there is right now.”
Jackson had alluded that something more than just swapping music occurred that night.
Rashida Jones & Tobey Maguire 1997-2000
Before Spiderman and Parks and Recreation, Rashida Jones and Tobey Maguire dated. Maguire broke things off right before his career took off thanks to Spiderman.
There were rumors that the two young lovers were engaged before they broke up, but neither of them confirmed if Maguire put a ring on it.
Maguire, he met his future wife, Jennifer Meyer in 2003. The two became engaged in April 2006. While engaged, Meyer’s gave birth to their daughter in November 2006. The couple wed in September 2007 in Hawaii. The couple welcomed their second child in May 2009. Unfortunately, the couple separated in 2016 and officially divorced in 2017.
Even though it’s uncertain if Maguire and Jones were ever engaged, Jones has definitely been engaged before. In 2003, Mark Ronson proposed to Jones on her 27th birthday with a crossword puzzle. They were engaged for a year before calling it quits. In 2018 Jones strayed away from the spotlight because she was secretly pregnant with musician Ezra Koenig’s son! Jones gave birth in August 2018.
Minka Kelly & Donald Faison 2004-2005
Donald Faison and Minka Kelly dated for less than a year. Kelly was definitely a rebound for Faison. They began dating soon after he separated from his first wife, Lisa Askey. They lasted less than a year and he quickly moved on to date CaCee Cobb, who he eventually married in 2012.
Kelly and Faison attended many red carpets together during their short relationship.
Despite being super public about their relationship they never talked about their romance to the press while together or after they broke up.
Helen Mirren & Liam Neeson 1980-1984
Before Helen Mirren was a Dame and Liam Neeson was known for Taken, the two actors dated in the 80s. The two met on the set of Excalibur. It was Neeson’s first significant role, as Sir Gawain, and Mirren was playing Morgana.
Many didn’t know about their romance back in the 80s because they weren’t he bigshot stars they are today. But in January 2018 the old couple reunited on the Graham Norton Show to promote their respective films.
Graham Norton asked about their past relationship to which Mirren responded, “We didn’t date, we lived together for four years. We were a serious item for a while. Lucky me!”
In a different interview, Neeson said that Mirren was “mesmeric” on set.
“She was so sexy. I thought, gosh, that’s Helen Mirren! She was as beautiful up close as on stage. Just so human. I was in love with this extraordinary human being,” Neeson said. “Can you imagine riding horses in shiny suits of armor, having sword fights, and you’re falling in love with Helen Murren? It doesn’t get any better than that.”
The couple broke up because of work. Mirren was getting job after job, while Neeson wasn’t working. Mirren said that he needed to “come out from under my wing” and be on his own to make it.
The two harbor no hard feelings towards each other.
Ashley Olsen & Lance Armstrong 2007
Actress turned designer Ashley Olsen and disgraced cyclist Lance Armstrong had a secret fling in 2007. New York Times scribe Juliet Macur publicized their secret romance in her ‘s tell-all book about Armstrong, Cycle of Lies: The Fall of Lance Armstrong.
According to Macur’s book, Armstrong’s friends were not happy about him dating Olsen because she was 15 years younger than him. They were worried Olsen would ruing his image.
Macur wrote that John Korioth, Armstrong’s friend and head of the Livestrong Foundation “warned the 36-year-old father of three that his May-December romance could damage his cancer work.”
Macur claims that Korioth told Armstrong, “Whoa, dude, bad idea. You’ve got to put a stop to this right now.” The friends got in a heated argument with Armstrong responding, “She’s 21…F**k you.”
Olsen and Armstrong were spotted out a few times, and someone saw them making out once. Their relationship fizzled out quick.
Katie Couric & Bob Saget
Katie Couric revealed in 2013 that she once went out with Bob Saget. Could you imagine if these two ended up lasting? While on Howard Stern’s show, Couric revealed that she went out with Saget but sparks didn’t fly and he never called her again.
Couric said Saget “was fun, he was really fun,” but there was nothing there between the two.
“I had fun, I don’t think I did it for him,” she admitted.
In that same interview, Couric revealed that she also went out with Jeff Probst, the host of Survivor, and he also didn’t call again.
“I can’t say that I was devasted that neither called me back,” She told Stern. “I thought they were both nice guys…I don’t think there was real magic there with either [of them], but I enjoyed spending time with them.”
Jamie Dornan & Keira Knightley 2003-2005
Before either Jamie Dornan or Keira Knightley were mega famous they were boyfriend and girlfriend. The two burgeoning actors met on a photo shoot and not a film set. They met in 2003 while modeling for Asprey, a British jewelry company.
After their modeling gig, the two began to date and attended red carpets and music festivals together.
After dating for a few years, they called it quits. Knightley began to gain worldwide fame thanks to the Pirates of the Caribbean franchise, and it was all too much. Dornan told The Daily Telegraph, “Being with Keira was an insight into how rotten [being famous] can be.”