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 posted a heartbreaking Instagram announcing their divorce? Or the ongoing mystery of Bella Hadid and the Weeknd? 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.
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. "It's always a mystery. You can't plan those things."
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.
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 back in 2009, 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."
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, "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."
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. "We have, in fact, ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another."
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 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."
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 to say it was him.
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 on why they broke up.
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, 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.
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. "'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."
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, 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."
Despite their 16-year age difference, 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 back in 2011 (presumably before he met his now-wife Eva Mendes), referring to Bullock and Rachel McAdams. "I haven't met anybody who could top them."
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.
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. "That's about all there is right now."
However, Jackson said in 2006 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.
Drake confirmed on The Ellen Degeneres Show 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."
Back in 2009, the Mad Men actress revealed in an interview with GQ 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."
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, but were confused as to how Shields could have gone from dating JFK, Jr. to Cage.
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 in an interview that year.
Lest you forget: Kim Kardashian and Nick Cannon dated 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.
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, LaBeouf described it as "probably the worst date either of us have ever had."
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, 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. "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 go way back—they've been co-stars in multiple movies and TV shows together, and apparently dated for a brief period of time while filming The Object of My Affection. Now, they're just really good friends.
In a 2012 interview with GQ, 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."
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 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.”
Last year on Watch What Happens Live With Andy Cohen, 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]."
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.
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 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,” . "I’m just kidding. That was a while ago, we’re just really good friends now.”
Liv Tyler and Joaquin Phoenix began dating when they were just 18 years old. Tyler told Elle Magazine 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.
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. "I'm really lucky that I'm on good terms with him."
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 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 recently.