When it comes to Hollywood, there's a lot of celebrity breakups and divorces, and it can be hard to keep up. Remember when Jenna Dewan and Channing Tatum (opens in new tab) posted a heartbreaking Instagram announcing their divorce? Or the ongoing mystery of Bella Hadid and the Weeknd (opens in new tab)? The sad trend has us reminiscing about the times when some of our other favorite Hollywood A-listers used to go out, and...actually, things turned out okay for them. Click through for a trip down memory lane with the stars you totally used to ship.
Penelope Cruz and Tom Cruise
While they may have met on the set of Vanilla Sky when Cruise was married, the couple didn't make their relationship public until the August 2001 premiere of Captain Corelli's Mandolin. The two split in 2004.
"I've never fallen in love with someone I'm working with. It's always been afterwards. If something becomes friendship, then maybe months later it becomes something else, but you can never know," she said to The Telegraph (opens in new tab). (opens in new tab) "It's always a mystery. You can't plan those things."
Rachel McAdams and Michael Sheen
Oh, on-set romances. These two met while filming Woody Allen's Midnight in Paris and confirmed it on the red carpet at the 2011 Cannes Film Festival. Before breaking up in 2013, the couple never went too long without seeing each other.
"Michael and I never spend more than three weeks apart -- we rack up a lot of air miles -- but you have to be quite adaptable in this business whether you are in a relationship or not," The Notebook star said. (opens in new tab)
Mila Kunis and Macaulay Culkin
Before her and Ashton Kutcher tied the knot, the actress dated Home Alone star Culkin from 2002 to 2011, they first got together when the Black Swan actress was 18-years-old, and he was 21-years-old.
In an interview with Women's Health (opens in new tab) back in 2009 (opens in new tab), she commented on their relationship. "We grew up together," she said. "You find a steady rock in your life, and that's all you need. We have our ups and downs, but work through them."
Alanis Morrissette and Ryan Reynolds
They met at Drew Barrymore's birthday party in 2002 and would announce their engagement two years later. The engagement lasted three years until they publicly broke it off in a statement to the public.
The Ironic singer spoke about the split to the L.A. Times in 2008 (opens in new tab), "I think it's the straw that breaks the camel's back," Morissette said. "I was a full-blown love addict, so it was like, 'I can't keep doing this, my body can't take it.' For someone who is a love addict, [breakups are] debilitating."
Cameron Diaz and Justin Timberlake
It was a romance only the '00s could produce and the '00s only. When Diaz and the *NSYNC met at the 2003 Nickelodeon Kids' Choice Awards slime, sorry, I meant sparks flew. That summer, she followed him on his tour with Christina Aguilera, and the pair would go on to date for four years.
The couple announced their split in 2007 in a statement,"It has always been our preference not to comment on the status of our relationship, but, out of respect for the time we’ve spent together, we feel compelled to do so now, in light of recent speculation and the number of inaccurate stories that are being reported by the media," the duo said. (opens in new tab) "We have, in fact, ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another."
Zachary Quinto and Jonathan Groff
Quinto confirmed he was dating the Mindhunter actor in an interview with Out Magazine in 2012.
"I'm incredibly happy, I'm incredibly lucky," he said of their relationship (opens in new tab)at the time compared to others. "I found myself in a pattern of being attracted to people who were somehow unavailable, and what I realized was that I was protecting myself because I equated the idea of connection and love with trauma and death."
Christina Applegate and Brad Pitt
The fling may have been brief, but we can't let you forget it. Applegate states they met when Pitt and Jason Priestly would come over for barbecues at her humble abode.
At the 1989 MTV Video Music Awards, she brought a smoking 26-year-old Pitt as her date only to ditch him halfway through the show. While she's never has admitted who the mystery man was, Gilmore Girls ' Sebastian Bach came forward (opens in new tab) to say it was him.
Cindy Crawford and Richard Gere
The couple met at a backyard BBQ at the home of their mutual friend, portrait photogrpaher Herb Ritts in 1988. Sure, Crawford was only 22-years-old when she met the 39-year-old Pretty Woman actor but love conquers all! The pair exchanged vows in December of 1991 at the Sin City chapel in Las Vegas, but would announce their divorce in 1995.
"I think I was more willing at 22 to be, like, 'Okay, I'll follow,' but then you start going, 'Well, I don't want to just follow—I want to lead sometimes and I want to walk side by side sometimes,'" she said (opens in new tab) on why they broke up.
Salma Hayek and Edward Norton
The Fight Club actor and the Frida actress dated from 1999 to 2003 after the two were set up by their chiropractor.
In 2017 in an opinion piece for the New York Times, (opens in new tab) Hayek credited Norton for his help in the 2002 film about the famous painter. "Thanks to a phalanx of angels who came to my rescue, including Edward Norton, who beautifully rewrote the script several times and appallingly never got credit," she wrote.
Anjelica Huston and Jack Nicholson
After leaving New York to move back home to Los Angeles in 1973, Huston met Nicholson at his birthday party in his Beverley Hills home. Despite the 14-year age gap, they would go on to be a couple for over two decades until he announced he was having a child with Rebecca Broussard in 1989.
"Paternally, he would call us 'my people.' At the time, the generality of it bugged me; I wanted to be special, and I felt a loss of identity, she wrote in Watch Me: A Memoir. (opens in new tab)"'Where are my people?' But there was very much a sense with Jack that one was on his team. And it was a good team to be on. A strong team."
Tom Cruise and Cher
The unlikely couple started a whirlwind romance when Tom Cruise's career was first starting and when Cher was at the peak of hers. In a segment called "Truth or Cher" on Watch What Happens Live with Andy Cohen (opens in new tab), the singer and actress confirmed that she once dated Cruise, who is 16 years younger than she is.
When Cohen asked where he ranked in the list of her lovers, Cher was quick to say, “He was in the top five. It’s not a long list, just a good list.” She goes on to say, "It could have been a great big romance, because I was crazy for him."
Ryan Gosling and Sandra Bullock
Despite their 16-year age difference (opens in new tab), The Notebook star and Sandra Bullock dated for a year back in 2002. They first met on the set of Murder by Numbers, and started their relationship soon after. Though it didn't last long, Gosling said Bullock was one of the best girlfriends he'd ever had.
"I had two of the greatest girlfriends of all time," Gosling said in an interview (opens in new tab) back in 2011 (presumably before he met (opens in new tab) his now-wife Eva Mendes), referring to Bullock and Rachel McAdams. "I haven't met anybody who could top them."
Sandra Bullock and Matthew McConaughey
The Time to Kill co-stars dated while filming the movie. And, although their romance reportedly last two years, neither Bullock nor McConaughey admitted to it when it was happening. She tried to deny they'd dated, but eventually gave in and hinted that they did.
"It's the work we both put in. There's a great amount of respect and love. I feel very cared for by Matthew. No matter where he is in his life or where I am in mine—he could be married—I know we would stay close," Bullock said in an interview with Cosmopolitan (opens in new tab).
Janet Jackson and Matthew McConaughey
After meeting at the 2002 Grammy Awards, Janet Jackson and Matthew McConaughey dated for a short period of time—though McConaughey never considered it a relationship."We swapped some good music and she's a dear lady. She's a sweetheart but we're not dating, we're just friends," he told Upscale Magazine (opens in new tab). "That's about all there is right now."
However, Jackson said in 2006 (opens in new tab) that they did date, but very briefly. "I guess we did [date]. He is such a great guy and a sweetheart. It was just for a minute, that's why I'm so hesitant to mention it," Jackson said.
Tyra Banks and Drake
Drake confirmed on The Ellen Degeneres Show (opens in new tab) that he and Tyra Banks went on one date together. And, although it was only a one-time thing, the two are still really good friends.
"It was just one date," he said. "We went to Disneyland in disguise actually, which was really fun. I don't even know if it was like a date. It was like a get-together. We're still really close."
Ashton Kutcher and January Jones
Back in 2009, the Mad Men actress revealed in an interview with GQ (opens in new tab) that her first boyfriend was Ashton Kutcher. However, the relationship didn't work out because he couldn't get behind Jones' career choice.
"[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—fuck 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."
Brooke Shields and Nicolas Cage
The model-slash-actress was rumored to be dating Nicolas Cage in 1987 when she was photographed attending the premiere of Cage's breakout film, Moonstruck. People believed their relationship was more serious off the red carpet (opens in new tab), but were confused as to how Shields could have gone from dating JFK, Jr. (opens in new tab) to Cage.
Courteney Cox and Michael Keaton
Courteney Cox and Michael Keaton dated for nearly six years, during which time they would bring home scripts and practice running lines together. Sadly, they made a joint decision to end their relationship in 1995. "It's the most important relationship I've ever had, and I think he's the most wonderful person I've ever met," Cox told People (opens in new tab) in an interview that year.
Kim Kardashian and Nick Cannon
Lest you forget: Kim Kardashian and Nick Cannon dated (opens in new tab) back in the early 2000s. The pair allegedly split after Kim's sex tap with Ray J. surfaced. Cannon went on to marry Mariah Carey in 2008, but the scandal affected him so much so that he and his now-ex-wife decided not to have sex before tying the knot (opens in new tab).
Shia LaBeouf and Hilary Duff
The Transformers actor had a brief fling with Hilary Duff, but their first date went so poorly that he didn't pursue her again. In an interview with Hollywood Life (opens in new tab), LaBeouf described it as "probably the worst date either of us have ever had."
Jared Leto and Cameron Diaz
Cameron Diaz has dated a lot of other big-name celebs, including Justin Timberlake, Alex Rodriguez, and Jared Leto. When she began dating Leto in 1999 (opens in new tab), they tried to keep their relationship a secret—but word got out. After a four-year romance, Diaz and Leto split. Twelve years later, the actress married her current husband, Benji Madden, and has completely forgotten about her previous relationships.
"Nothing matters now that I have my husband," explained on Cohen's SiriusXM show (opens in new tab). "I don't even remember any of that. Like, that's the thing. That's how I know he's my husband because there's…no one compares. Everything else just washes and slips away."
Jennifer Aniston and Paul Rudd
Jennifer Aniston and Paul Rudd go way back—they've been co-stars in multiple movies and TV shows together, and apparently dated for a brief period of time (opens in new tab) while filming The Object of My Affection. Now, they're just really good friends.
In a 2012 interview with GQ (opens in new tab), when asked if it was weird to kiss her friend onscreen, Aniston said,"Nah. I’ve kissed him for years." Rudd chimed in and added, "We've made out for decades."
Justin Timberlake and Fergie
Back in 2003, the Black Eyed Peas singer and Man of the Woods singer collaborated on the song,"Where is the Love?" and reportedly dated for a brief amount of time. In a 2003 interview (opens in new tab) with Cosmopolitan, Fergie said it was more of a casual fling.
“One of my good friends was dating J.C. Chasez, and so we’d all hang out with ‘N Sync. Justin and I would go out together and have fun and make out,” Fergie said. “We went to Hawaii together, but we were never serious. He was Mr. Right Now.”
Jenna Dewan and Justin Timberlake
Last year on Watch What Happens Live With Andy Cohen (opens in new tab), the actress-slash-dancer-slash-businesswoman recalled the time she was one of Justin Timberlake's backup dancers. Dewan confirmed that she and Timberlake dated for a short period of time after he and Britney Spears split, but assured that she was not the rebound.
"We dated, not that long. We were like friends...that dated," she said. "I was not the rebound! I was very clear not to be [that]."
Leonardo DiCaprio and Gisele Bündchen
Before she was married to Tom Brady, Gisele Bündchen dated Leonardo DiCaprio—and it wasn't just a casual fling. The two were together for five years before splitting in 2005. Four years later, the model still had nothing but nice things to say about the Titanic actor.
"We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best," she told Access Hollywood (opens in new tab).
Josh Hutcherson and Vanessa Hudgens
Shortly after splitting with her High School Musical co-star Zac Efron, Vanessa Hudgens reportedly began dating her Journey 2: The Mysterious Island co-star Josh Hutcherson. However, the relationship didn't last long.
When asked how long they'd been dating in an interview (opens in new tab) on the Australian version of TODAY, Hutcherson confirmed they once dated. “We’re not…No. We were at one point, but she broke my heart,” Josh joked. "I’m just kidding. That was a while ago, we’re just really good friends now.”
Joaquin Phoenix and Liv Tyler
Liv Tyler and Joaquin Phoenix began dating when they were just 18 years old. Tyler told Elle Magazine (opens in new tab) that despite their breakup, they are still friends because he was such a big part of her life.
"I'm friends with all my exes! I love them so much! I guess it depends on what happens, right? I consider Joaquin and all of his sisters to be like family. We were so young when we were together, like 18 to 21. He was my first love. So he's a huge part of even my sense of humor," she said in the interview.
Matt Damon and Winona Ryder
Back in 1997, Matt Damon and Winona Ryder were introduced by Gwyneth Paltrow who was at the time dating Damon's best friend, Ben Affleck (click to the next slide to see yet another of Paltrow's famous exes). After hitting it off, Damon and Ryder started dating, and Ryder was Damon's date to the 2000 Golden Globes when he was nominated for the movie The Talented Mr. Ripley (along with Paltrow).
Things didn't end up working out, but Ryder had nothing but good things to say about Damon. "Matt couldn't be a greater, nicer guy," she said in an interview (opens in new tab). "I'm really lucky that I'm on good terms with him."
Luke Wilson and Gwyneth Paltrow
The Oscar winning actress may have just secretly married Brad Falchuck (opens in new tab), but long before him, Gwyneth Paltrow dated Luke Wilson. The Royal Tenenbaums co-stars reportedly dated for a year (opens in new tab) before she met her first husband, Chris Martin.
Madonna and Michael Jackson
Madonna confused the world when she brought Michael Jackson as her date to the 1991 Academy Awards. The two attended the after parties together, and were even seen out on a dinner date a few days later. At the time, people were convinced it was a publicity stunt (opens in new tab) for Madonna's documentary, "Truth or Dare." But the Material Girl certainly considered it a date, and even posted a throwback pic on her Instagram (opens in new tab) recently.
David Arquette and Drew Barrymore
The Never Been Kissed brother and sister co-stars had a very different relationship off-camera. Though Barrymore denies it, Arquette said they used to date—long before they starred in the movie together. “We also dated, but she denied it on Howard Stern,” Arquette said (opens in new tab) in an episode of PeopleTV’s Couch Surfing. “But, we dated, Drew!”
Heather Graham and Matthew Perry
In 2003, the Friends star and Hangover actress reportedly "hooked up" for a bit, according to E! News (opens in new tab). However, it was nothing more than a short-lived fling.
Miley Cyrus and Nick Jones
The former Disney Channel stars dated when they were teens, but never actually confirmed the "Niley" rumors until after the relationship was over. The split took a big toll on Cyrus, who began dying her hair after the breakup.
"At first I bawled for a month straight. I was so sad. I just went into this weird funk. And I dyed my hair black," Cyrus told Seventeen (opens in new tab). "When we were dating, Nick wanted me to get highlights—and so I did that, and I got myself looking great. And then, on the day we broke up, I was like, I want to make my hair black now—I don’t want to look pretty; I want to look hard-core. I was rebelling against everything Nick wanted me to be. And then I was like, I've got to be by myself for now, and just figure out who I really am."
Alexis Bledel and Milo Ventimiglia
The on-screen couple (a.k.a Rory Gilmore and Jess Mariano) also dated in real life. Their romance began in 2001, just one year after becoming Gilmore Girls co-stars. And though Bledel said they had talked about marriage, the two split up after four years together.
"I think everybody who has been dating for more than a couple of years probably talks about it at some point," Bledel told People (opens in new tab) back in September 2005. "It's a fun thing for us to talk about, but that's it."
Kristen Johnson and Ryan Reynolds
Long before he was married to Blake Lively (opens in new tab), Ryan Reynolds had a lot of short-lived girlfriends (and a marriage to Scarlett Johansson (opens in new tab)!), including his one-time date Kristen Johnston. (opens in new tab) The two attended the 1999 premiere of The Green Mile together, but nothing more after that.
Natalie Portman and Jake Gyllenhaal
Back in 2006, Natalie Portman and Jake Gyllenhaal had a brief romance. Despite their split, they remain friends to this day, and he's even joked about what it was like dating the Black Swan star.
"She's a vegan, which makes it really frustrating when you're picking a place to eat," he joked when presenting her the "Desert Palm Achievement Award (opens in new tab)" in 2011—though it's likely that's not why they broke up.
Sarah Jessica Parker and Michale J. Fox
The Back to the Future star and the Sex and the City star used to be an item in the 1980s. The relationship reportedly lasted a year, but despite their many photos together, there was speculation that the couple was together as a PR stunt (opens in new tab).
Sarah Jessica Parker and Robert Downey Jr.
After dating Fox and before SJP married Matthew Broderick, she and Robert Downey Jr. dated for almost seven years. In 2008, the Iron Man star admitted his drug and alcohol abuse led to the downfall of their relationship.
"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. She tried to help me. She was so miffed when I didn't get my act together," he told Parade (opens in new tab).
Jennifer Lopez and Diddy
After Jennifer Lopez's divorce from Ojani Noa in 1998, the singer-slash-makeup-mogul (opens in new tab) went on to date Sean Combs (a.k.a Diddy) for about a year-and-a-half. Diddy once said in an interview (opens in new tab) that J.Lo was one of his greatest loves "without doubt," but she revealed his infidelity was the cause of their split in 2001.
Kate Hudson and Alex Rodriguez
After her divorce from Chris Robinson in 2009, Kate Hudson got together with the former Yankees slugger. A-Rod has been around the bases when it comes to girlfriends, and he apparently wasn't over Madonna when he was dating Hudson, which led to their breakup.
"Kate was mad with jealousy," a source told Daily Mail (opens in new tab). "She gave A-Rod three chances to stop contacting Madonna. How would you feel if your new boyfriend kept calling his ex?"