Celebrity Duos We Wish Were Still Couples
Hollywood hookups and breakups are big news, and it can be hard to keep track of who’s dating who. And when a celebrity appears to have found the one, all past partners pale in comparison.
But just like the rest of us, most famous folk have a pretty mixed bag of exes, and even though they didn’t go the distance, it all turned out fine in the end. You might have forgotten about these former celebrity couples — but let us refresh your memory. Get ready for a taste of nostalgia!
Courteney Cox and Michael Keaton
Michael Ferguson / AP Photo
Length of Relationship: 5.5 years
Courteney Cox met Michael Keaton through a mutual friend after Cox revealed how much she liked Keaton’s performance in the 1988 film “Clean and Sober.” The “Friends” star told PEOPLE that they had their first date at her house and “talked for five hours.”
This was a pattern they followed for their entire relationship — rarely appearing together in public.
In Their Own Words
Cox said it was a joint decision to end the relationship — and clearly an emotional one.
“It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” she said. “We still love each other.”
Keira Knightley and Jamie Dornan
AP Photo
Length of Relationship: 2 years
Keira Knightley and Jamie Dornan started dating in 2003, long before she was an Oscar-nominated actress and he was making headlines as the “Fifty Shades” franchise’s Christian Grey.
In Their Own Words
In 2006, after their split, Dornan reportedly said, “There is a big pressure when you go out with someone such as Keira. The man is meant to be the alpha in the relationship on the money and power front, and clearly I was not. You feel like you have to be dominant in other areas and that causes problems.”
Brad Pitt and Juliette Lewis
John Barrett / AP Photo
Length of Relationship: 4 years
Brad Pitt and Juliette Lewis were together from 1989 to 1993, after meeting on the set of “Too Young to Die.”
Before they split in 1993, Lewis told Los Angeles Times: “We’re like at the point in love, where we just like to see each other every single day, and we don’t get bored with each other, so it’s really, really nice. Also we get to be around each other when we’re working and talk and collaborate. We want to work together again and again and again.”
In Their Own Words
In 1995, Pitt had nothing but good things to say about Lewis to Vanity Fair.
“I still love the woman,” he said. “There’s some real genius there. I had a great time with her. It was one of the greatest relationships I’ve ever been in. The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?”
Wilmer Valderrama and Mandy Moore
AP Photo
Length of Relationship: About a year
Just like everyone else, sometimes celebrity relationships don’t end well. Five years after their 2001 split, Wilmer Valderrama told Howard Stern that he took his then-teen girlfriend Mandy Moore’s virginity.
Moore clapped back in an interview with ELLE later that year, describing Valderrama’s remark as “utterly tacky, not even true, and it hurt my feelings because I like him.”
In Their Own Words
In 2018, Moore told Stern how she felt at the time.
“I dated him when I was 16 and 17,” she said. “I love him and I still love him, and he’s a very good friend and that’s why I was so shocked by it because not only was it a fib, but it was so unlike him, it was so uncharacteristic.”
Cher and Tom Cruise
AP Photo
Length of Relationship: Unknown
Cher and Tom Cruise met at Sean Penn and Madonna’s wedding in Malibu in 1985 and immediately found common ground — they’re both dyslexic.
“We didn’t go out til way later, but there definitely was a connection there,” she told the Daily Mail in 2018.
In Their Own Words
Cher, who also dated Richie Sambora, Val Kilmer, Gene Simmons and Gregg Allman, also revealed that she and Cruise are still friends, although some conversation topics are off the table.
“I don’t get what he does, that whole Scientology thing,” she said. “I can’t understand it so I just … don’t.”
Hilary Duff and Joel Madden
Mark J. Terrill / AP Photo
Length of Relationship: 2 years
Hilary Duff was only 16 when she dated Good Charlotte vocalist Joel Madden. They split in 2006 and were quick to tell the media that it was amicable.
“Every girl I’ve ever dated I have respect for, and I always try to leave them in good terms,” Madden told PEOPLE in 2007. “I don’t see the necessity to be friends with anyone you’ve dated but definitely out of respect of the time, you have to be kind of respectful and that’s what I try to do.”
In Their Own Words
In 2016, Duff revealed on The Love Bomb Podcast that her relationship with Madden was a huge deal at the time.
“It was so intense. It was my life,” she said. “It was like every minute of my day. It was pretty major.”
Sandra Bullock and Ryan Gosling
AP Photo
Length of Relationship: About a year
After meeting on the set of the thriller, “Murder by Numbers,” in 2002, Sandra Bullock and Ryan Gosling became a couple.
Gosling went on to date Rachel McAdams, his “The Notebook” co-star, and he’s been in a relationship with Eva Mendes, mom of his two daughters, for more than nine years.
In Their Own Words
Meanwhile, Bullock — who also has two kids — has been with Bryan Randall since 2015.
“Bryan is such a sweet soul, and things couldn’t be more different from the toxic relationships she’s been in before,” a friend of Bullock exclusively told Us Weekly in June 2019.
Courtney Love and Edward Norton
Gael Cornier / AP Photo
Length of Relationship: 4 years
After co-starring in the 1996 movie, “The People vs. Larry Flynt,” Courtney Love and Edward Norton dated for four years. It was reportedly a pretty volatile pairing, and 10 years after their split, Love still had a major cross to bear.
In Their Own Words
In a series of tweets in 2010, Love called Norton a “terrifically bad sexist” and demanded he pay her back $300,000 she claimed he owed her.
However, Love also had good things to say about her ex. In 2011, she told Page Six, “[Norton] has great character. He’s very political. I see him being a senator one day.”
In Their Own Words
In 2017, Fenn described Depp as her “first love,” telling The Big Issue, “We were so young. I met him when I was 19 and he was 21. We went out for 2.5 years when we were just starting out in the business. He was very sweet.”
Jennifer Garner and Michael Vartan
AP Photo
Length of Relationship: About a year
Jennifer Garner’s best-known relationship is with her ex-husband (and father of her three kids) Ben Affleck. But before Affleck, and after filing for divorce from her first husband Scott Foley, she dated her “Alias” co-star Michael Vartan.
It was a short relationship, but a 2018 social media tribute revealed she still had a special place in her heart for him.
In Their Own Words
“Can you believe this baby face is 50?! Happy birthday, #MichaelVartan,” Garner wrote on Instagram alongside a throwback shot of them in character.
She added the hashtags #alwaysanALIASgirl and #sydneyandvaughnforever.
Jennifer Aniston and John Mayer
Chris Carlson / AP Photo
Length of Relationship: About a year
John Mayer has form for throwing shade at his exes, and Jennifer Aniston is one former girlfriend who didn’t escape a public put-down.
The couple dated from 2008 to 2009 after meeting at an Oscars party, and in a subsequent interview with Playboy, the singer suggested that the age gap (Aniston is eight years older) was an issue.
In Their Own Words
“I’ll always be sorry that it didn’t last,” he said. “In some ways I wish I could be with her. But I can’t change the fact that I need to be 32.” He also said, “The brunt of [Aniston’s] success came before TMZ and Twitter. I think she’s still hoping it goes back to 1998. She saw my involvement in technology as courting distraction.”
Owen Wilson and Sheryl Crow
AP Photo
Length of Relationship: 2 years
After meeting on the set of “The Minus Man” in 1999, Owen Wilson and Sheryl Crow became a couple. On the liner notes of her 2002 album “C’mon, C’mon,” Crow dedicated the song “Safe and Sound” to Wilson.
In Their Own Words
In 2019, Crow joked about not being married, telling the audience at the 44th Annual Gracie Awards in California that she had been engaged three times and “had a rockin’ great time not getting married.”
Cameron Diaz and Justin Timberlake
Danny Moloshok / AP Photo
Length of Relationship: 4 years
The story goes that Cameron Diaz and Justin Timberlake first met at the 2003 Kids Choice Awards, when the “Charlie’s Angels” star presented the former NSYNC frontman with the prize for “Best Burp.”
It was the award she won in 2001, showing that even a burp can form the basis of a beautiful relationship. However, it wasn’t to last, and they split four years later.
In Their Own Words
The pair have remained on good terms, even doing a sex scene together in the raunchy 2011 comedy “Bad Teacher.”
Yes, you read that right!
Ashton Kutcher and January Jones
AP Photo
Length of Relationship: Unknown
According to InStyle, January Jones and Ashton Kutcher started dating in the late 1990s and even lived together in Los Angeles.
Since their split, there’s been a lot of speculation about what went on behind closed doors.
In Their Own Words
In 2009, the “Mad Men” star told GQ about “the guy I was dating when I first got to L.A.,” explaining that he “was not supportive” of her acting, which one can only guess could be Kutcher.
“He was like, I don’t think you’re going to be good at this,” she said. “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.”
Winona Ryder and Matt Damon
Mark J. Terrill / AP Photo
Length of Relationship: 2 years
It was apparently Winona Ryder’s then-BFF Gwyneth Paltrow who introduced her to Matt Damon back in 1997.
However, Damon was involved with Minnie Driver at this time, and things got even more complicated when he told Oprah Winfrey he was single during a 1998 interview — reportedly news to Driver.
In Their Own Words
Although their relationship didn’t last, Ryder and Damon still have a great deal of love and admiration for each other.
“Matt couldn’t be a greater, nicer guy,” Ryder told Black Book in 2009. “I’m really lucky that I’m on good terms with him.”
Tyra Banks and Seal
AP Photo
Length of Relationship: Several months
Some people are very good at keeping their relationships under the radar despite their huge profiles.
Take Tyra Banks and Seal, for instance. They dated for several months in 1996.
In Their Own Words
Because they were so secretive, we don’t have any words spoken from either one about the other. But what we do know is that Seal went on to marry and have kids with Banks’ fellow supermodel Heidi Klum while the “America’s Next Top Model” host welcomed a son with Norwegian photographer Erik Asla in 2016.
She’s now reportedly dating Canadian businessman Louis Bélanger-Martin, although she’s remaining as tight-lipped as ever.
Drew Barrymore and David Arquette
AP Photo
Length of Relationship: Unknown
In 2014, David Arquette appeared on “Watch What Happens Live” and divulged that he and his “Never Been Kissed” co-star, Drew Barrymore, who played his younger sister in the film, actually dated years previously.
In Their Own Words
“[Drew and I] used to date when we were very young kids. Well, not little kids!” he said. “She’s just one of the sweetest, kindest people in Hollywood. She always has been, and she always will be. She’s just a lovely, sweet person. We used to run around and just be silly.”
Kirsten Dunst and Jake Gyllenhaal
Mark J. Terrill / AP Photo
Length of Relationship: Less than 2 years
Kirsten Dunst and Jake Gyllenhaal dated for just under two years after Gyllenhaal’s sister Maggie introduced them.
She and Dunst both starred in the 2003 movie “Mona Lisa Smile.”
In Their Own Words
What happened in their relationship and led to their split is anyone’s guess — they’re both extremely private about their personal life.
However, in 2009, Dunst hinted that there wasn’t much of a bond remaining. “It would be nice to see him,” she told Allure. “But we’re not good friends.”
Sarah Jessica Parker and John F. Kennedy Jr.
AP Photo
Length of Relationship: 6 months
If The New York Times has it right, Sarah Jessica Parker and John F. Kennedy Jr. first met at the theater, and Kennedy made the first move. According to Parker’s friend, Adam Shankman, the actress called him, screaming, “You’re not going to believe who asked me out!’”
They dated for about six months, a time Parker later referred to as “the Kennedy fiasco.” Apparently, SJP was overwhelmed by the attention that accompanied their relationship.
In Their Own Words
“We would go places where there wasn’t a soul around, and the next day I’d see pictures of us there in the tabloids,” she told The New York Times. “I have been a semi-public person since [starring in ‘Annie’ on Broadway as a child], but I never had any idea what real fame was until I met John. He’s a nice man, but for God’s sake, I feel like I should apologize for dating him. It has become the defining factor in the person I am. It’s pathetic.”
Shia Labeouf and Carey Mulligan
Charles Sykes / AP Photo
Length of Relationship: About a year
Shia Labeouf and Carey Mulligan met on the set of “Wall Street 2: Money Never Sleeps” in 2009 and dated for about a year.
LaBeouf later revealed the split from Mulligan (who’s now married to Mumford & Sons frontman Marcus Mumford) was due to their incompatible lifestyles.
In Their Own Words
LaBeouf told The Sunday Times Magazine, “Carey is not just an actress, she is a great human being, a sweet girl and super intelligent. Our thing came down to not having compatible work/lifestyles.
“We were always traveling and had sensibility differences that weren’t conducive to living with one another,” the actor continued. “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… Sensibilities, cultures, histories. There were differences, that’s all.”
Christina Applegate and Brad Pitt
AP Photo
Length of Relationship: About a year
Christina Applegate and Brad Pitt were a couple from 1988 to 1989, but it all came to an end at the 1989 MTV Video Music Awards. In 2015, Applegate appeared on “Watch What Happens Live” and told host Andy Cohen that she’d ditched Pitt the night of the VMAs for another man.
In Their Own Words
Applegate didn’t share the name of the mystery man, but the following year Skid Row singer and “Gilmore Girls” star Sebastian Bach stepped forward.
On the radio show “Elliot in the Morning,” Bach said, “[Christina] was interviewed recently on, like, ‘Entertainment Tonight,’ or something, and they said, ‘What was the dumbest thing you ever did?’ And she goes, ‘One night I ditched Brad Pitt for this other dude.’”
Heath Ledger and Naomi Watts
Kevork Djansezian / AP Photo
Length of Relationship: 2 years
Heath Ledger and Naomi Watts dated for a couple of years in the early Noughties and were photographed together at a film party for “Ned Kelly” in 2003.
In Their Own Words
“We had a beautiful relationship, only a couple of years, but he was a man who was completely full of joy, and there was a lot of laughing and affection,” Watts told More Magazine about Ledger in October 2011. “He was really a very special soul and made a great impact on my life.”
Jennifer Lopez and Wesley Snipes
AP Photo
Length of Relationship: Less than a year
Jennifer Lopez has had plenty of high-profile relationships, but Wesley Snipes is one old flame who might come as a surprise.
The two starred together in “Money Train,” which was filmed soon after Lopez broke up with her high school sweetheart.
In Their Own Words
She and Snipes dated briefly in 1995, and Lopez later admitted that Snipes’ “flirting” with her on set eventually “started getting a little more serious.”
Speaking of J.Lo and serious…
Alex Rodriguez and Kate Hudson
AP Photo
Length of Relationship: About a year
OK, so there’s still some mystery surrounding this one. Kate Hudson and Alex Rodriguez reportedly met at the reopening of the Fontainebleau Hotel in Miami in late 2008, with an eye witness reporting that they were flirting up a storm.
When the next baseball season started, Hudson was a regular fixture in the stands, grinning and cheering for A-Rod. However, neither of them ever confirmed the relationship.
In Their Own Words
In an article for Harper’s Bazaar that went live shortly before they went their separate ways in late 2009, Hudson suggested that whatever they had wasn’t serious. “I have a child, and there are people involved, and it’s unfair to talk about somebody else, especially when you’re not in that place yet to be discussing those things,” she said. “If I was sitting here with a belly out to here, I’d be talking about what the relationship is and how important that is in my life right now.”
Of course, Rodriguez is now engaged to Ms. Lopez.
Cameron Diaz and Matt Dillon
AP Photo
Length of Relationship: 3 years
Cameron Diaz and Matt Dillon first met in 1995 while they were shooting respective films in Minnesota (“Feeling Minnesota” and “Beautiful Girls”), but didn’t start dating until the following year.
They kept it low-key but occasionally gushed about one another to the press.
In Their Own Words
Diaz told The Guardian in 1997, “I love him incredibly.”
And Dillon told Parade in 2006, “I fell in love. It’s a very powerful thing when you feel that way about somebody. Cameron was a muse for me. I hadn’t been in any deep emotional relationships.”
Ryan Reynolds and Alanis Morissette
Chris Pizzello / AP Photo
Length of Relationship: 5 years
Fellow Canadians Alanis Morissette and Ryan Reynolds got engaged in 2004, two years after reportedly meeting at Drew Barrymore’s birthday party.
In Their Own Words
Morissette told People that she “felt so loved by him, in a trampoline kind of way.”
But three years later, they announced their split. “They remain close friends and continue to have the utmost love and admiration for each other,” their reps said in a joint statement.
Whoopi Goldberg and Ted Danson
Malcolm Clarke / AP Photo
Length of Relationship: 2-3 years
Actors Whoopi Goldberg and Ted Danson first met on “The Late Show Starring Joan Rivers” in the late 1980s. At the time, Danson was married to Casey Coates, but he and Goldberg struck up a friendship and started collaborating on work projects.
When they co-starred in the 1993 movie “Made in America,” rumors of an affair started circulating.
In Their Own Words
Their romance became public after Danson’s divorce, and some sources even said they planned to marry, but a couple of years later, they went their separate ways.
Pressure from his parents and the fact that he’d “walk in Whoopi’s shadow for the rest of my life” are partly to blame.
Bradley Cooper and Renee Zellweger
AP Photo
Length of Relationship: 2 years
Renee Zellweger and Bradley Cooper started dating in 2009 after meeting on the set of “Case 39.”
They split after two years, but remained on good terms. During the 2020 Oscars ceremony, they were photographed chatting and smiling.
In Their Own Words
It was a low-key relationship, largely kept out of the public eye.
Cooper told Entertainment Tonight in 2010 that he “loved coming to work and acting with [Zellweger] because he could “learn so much from her.”
Reese Witherspoon and Jake Gyllenhaal
Gus Ruelas / AP Photo
Length of Relationship: 2 years
After co-starring in the 2007 drama, “Rendition,” Reese Witherspoon and Jake Gyllenhaal’s relationship took a romantic turn, something that Witherspoon didn’t expect.
In Their Own Words
A friend of hers told People that she developed “this little crush over time.”
Everyone had high hopes for the cute couple, but they split in 2009, amid reports that Gyllenhaal wanted to get married, while Witherspoon wasn’t so sure (she’d recently divorced the father of her two kids, Ryan Phillippe).
Julia Roberts and Kiefer Sutherland
Mark J. Terrill / AP Photo
Length of Relationship: About a year
Things were pretty complicated for Julia Roberts and Kiefer Sutherland when they first got together on the set of “Flatliners” in 1990. Roberts was engaged to Dylan McDermott, and Sutherland was still married to his first wife, Camelia Kath.
Roberts ended things with McDermott, and Sutherland divorced Kath, but that wasn’t the end of the drama.
In Their Own Words
Sutherland was rumored to have cheated on Roberts, and then only days before marrying Sutherland, Roberts ran off with his friend, Jason Patric.
It seems the decision to call off the wedding, however, was mutually appreciated. Sutherland even told Rolling Stone, “I commend Julia for seeing how young and silly we were, even at the last minute, even as painful and as difficult as it was. Thank God she saw it.”
Chris Pine and Zoe Kravitz
Length of Relationship: Unknown
Chris Pine and Zoe Kravitz were romantically linked in 2010, then again in 2013.
In Their Own Words
It’s still unclear if these two ever dated, though, with sources telling the press in 2015 they were “good friends” and “get along great.”
In 2019, Pine and his girlfriend Annabelle Wallis attended Kravitz’s Paris wedding to Karl Glusman.
Matthew Morrison and Lea Michele
Length of Relationship: “A Broadway beat”
In Lea Michele’s 2014 autobiography “Brunette Ambition,” she revealed that she and her “Glee” co-star dated very briefly.
In Their Own Words
“Matt had been a friend of mine for years, and in fact, we’d actually dated back in the day for a Broadway beat,” she wrote.
Michele also addressed rumors that they were involved during the filming of “Glee,” telling Hollywood.com that “people are going to make things up. I think it’s just because we really are so close.”
Emily Blunt and Michael Buble
Dan Steinberg / AP Photo
Length of Relationship: 3 years
Emily Blunt and Micheal Buble dated from 2005 to 2008, and when they split, rumors spread that it was because Buble had cheated.
In Their Own Words
But he set the record straight in 2015, telling ET Canada, “Emily is a beautiful and loving person, and I’m grateful for the time I had with her, for the relationship. Without it, I wouldn’t have had a chance to fall in love with myself enough to be with a woman like my wife. It didn’t end because of cheating. It ended because we weren’t right for each other, and we are now exactly where we’re supposed to be in our lives.”
Penelope Cruz and Tom Cruise
Ric Francis / AP Photo
Length of Relationship: 3 years
After meeting on the set of the movie, “Vanilla Sky,” Penelope Cruz and Tom Cruise grew closer and went public with their relationship at the August 2001 premiere of “Captain Corelli’s Mandolin.”
The couple split in 2004.
In Their Own Words
“I’ve never fallen in love with someone I’m working with. It’s always been afterward. If something becomes friendship, then maybe months later, it becomes something else, but you can never know,” Cruz told The Telegraph. “It’s always a mystery. You can’t plan those things.”
Paris Hilton and Benji Madden
Chris Pizzello / AP Photo
Length of Relationship: 9 months
Good Charlotte rocker Benji Madden is married to Nicole Richie, but back in 2008, he dated her once-bestie, heiress Paris Hilton. But after nine months, they called time on their romance.
In Their Own Words
A source close to Hilton told People, “She is saddened by the breakup, but they’re just too different, and they wanted different things in life. He was loyal and sweet, but it was time to take a break.”
