Celebrities You Totally Forgot Dated Each Other

1 | Madonna and Tupac

The late rapper Tupac lived a lot of life despite dying at the age of 25, and that included a brief relationship with Madonna. It actually wasn’t until a 2015 interview with Howard Stern (via Vogue) that Madonna revealed they had dated, and two years later, TMZ unearthed a breakup letter Tupac had supposedly written her from jail.

For the pairing everyone was talking about during your formative years, This Was the Biggest Celebrity Couple the Year You Graduated.

2 | Elizabeth Taylor and Colin Farrell

It’s kind of mind-blowing that this couple even existed, but they totally did. In 2013, Colin Farrell revealed that he’d had an affair with Hollywood legend Elizabeth Taylor (who was 40 years older than him), telling Ellen DeGeneres that they’d been close for about two years and that they’d talk on the phone late at night. Who knew?

3 | Tom Cruise and Cher

Before Tom Cruise married Nicole Kidman or Katie Holmes, believe it or not, he and Cher were a thing. In a 2018 interview with Mail on Sunday, Cher confirmed that she and Cruise dated after meeting at a White House event for people with dyslexia in 1985, though their relationship didn’t last long.

For onscreen pairs who didn't get along offscreen, check out 11 Beloved Movie Couples Who Clashed Behind the Scenes.

4 | Cameron Diaz and Matt Dillion

They were only together for about two years, but from 1996 to 1998, Cameron Diaz and Matt Dillon were a total "it" couple. They originally met while they were both filming movies in Minnesota. By the time the year their comedy It's Something About Mary came out, their relationship eventually had run its course. But Dillon later told People that Diaz was his “muse.”

5 | Jennifer Lopez and Diddy

Long before she decided to settle down with Alex Rodriguez, Jennifer Lopez dated rapper and producer Diddy for two years. The most memorable moment in their relationship? Oh, probably the time they got arrested for having a loaded gun in the car with them, of course. The charges were eventually dropped, and by February 2001, Diddy released a statement that they had gone their separate ways.

For Hollywood marriages that have stood the test of time, check out The Longest-Lasting Marriages in Hollywood.

6 | Anne Heche and Ellen DeGeneres

It’s hard to imagine Ellen DeGeneres with anyone other than Portia de Rossi these days, but before the comedian and host began dating the woman she would marry, DeGeneres was with actor Anne Heche. They dated from 1997 to 2000, and although Heche claimed on this recent season of Dancing With the Stars that Fox threatened to dissolve her contract with them if she brought DeGeneres to the premiere of her movie Volcano, Heche did it anyway.

7 | Kate Hudson and Alex Rodriguez

Kate Hudson and Alex Rodriguez dated for such a short time back in 2008 that it’s easy to forget they were ever an item. According to what sources told The Daily Mail, they split because Rodriguez wasn’t over Madonna, his ex.

For splits that really hurt, check out 15 Celebrity Couple Breakups You're Probably Still Mourning.

8 | Rachel McAdams and Michael Sheen

These days, Rachel McAdams is married to Jamie Linden, but in 2011, she and Michael Sheen began dating after they met on the set of Midnight in Paris. Two years later, they called it quits, reportedly because McAdams was ready to settle down and start a family and Sheen wasn’t.

9 | Renee Zellweger and Bradley Cooper

From 2009 to 2011, Renee Zellweger and Bradley Cooper were a pretty serious couple—so serious, in fact, that for part of their relationship, they even lived together. They first met while filming Case 39, and they seem to have remained on pretty good terms. They were even spotted catching up at the 2020 Oscars, where Zellweger won the Best Actress trophy.

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10 | Alanis Morissette and Ryan Reynolds

Before there was the adored Hollywood couple that is Ryan Reynolds and his wife Blake Lively, he was actually dating singer-songwriter Alanis Morissette. The two Canadians were even engaged for three years before they went their separate ways in 2007. Like any artist would, Morissette went on to write about their relationship in her music, including her song “Torch.”

11 | Jessica Biel and Chris Evans

Chris Evans was a few years away from putting on Captain America's suit when he and Jessica Biel dated. They first started seeing each other back in 2001, when she was still starring on 7th Heaven, and the two acted together in a couple of movies, including Cellular, before they broke up in 2006.

12 | Wilmer Valderrama and Mandy Moore

Despite their 13-year age difference, Wilmer Valderrama and Mandy Moore dated from 2000 to 2002, and even after their relationship ended, there was still drama. Moore admitted she was hurt when Valderrama went on Howard Stern’s radio show and said that he had taken her virginity—something that the This Is Us star told Elle was “not even true.”

13 | Tyra Banks and Seal

When it comes to singer Seal’s past loves, the first to come to mind is likely his ex-wife Heidi Klum, but she’s not the only model he’s been with. He and Tyra Banks dated for a short period of time in 1996, and they kept things so private that little is known about their relationship.

14 | Emily Blunt and Michael Bublé

Actor Emily Blunt and singer Michael Bublé are now married to other people (John Krasinski and Luisana Lopilato, respectively), but they once dated each other. Unfortunately, it all came to an end in 2008 amid rumors that Bublé had cheated, which he later told Entertainment Tonightwere false.

"It didn't end because of cheating," he said at the time. "It ended because we weren't right for each other, and we are now exactly where we're supposed to be in our lives."

15 | Melissa Etheridge and Tammy Lynn Michaels

Once upon a time, musician Melissa Etheridge and actor Tammy Lynn Michaels were married… and then, in 2010, it all came to an end in a very explosive, very public divorce. For years after their split, there were court battles over the decisions they made about their children, including whether or not they’d be vaccinated.

16 | January Jones and Ashton Kutcher

Yes, before Demi Moore and Mila Kunis, Ashton Kutcher dated Mad Men star January Jones. In the late ‘90s, the two were apparently pretty serious about each other, but it just wasn’t meant to be, and they ended up splitting.

17 | Courteney Cox and Michael Keaton

Before Courteney Cox played Monica on Friends, she started dating Batman star Michael Keaton. They first met in 1989 and then went on to date for six years. Despite rumors that they were getting engaged, Cox and Keaton broke up in 1995, with Cox telling People, “Nothing about our relationship was ever simple.”

18 | Matt Damon and Minnie Driver

Good Will Hunting costars Matt Damon and Minnie Driver had been dating for over a year when he decided to end their relationship the most dramatic way possible—on national television. When Damon told Oprah Winfrey that he was single on a 1998 episode of The Oprah Winfrey Show, it was the first Driver was hearing about it. “It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate. Of course, he was busy declaring his love for me on David Letterman a month previously,” Driver later told the LA Times.

19 | Sandra Bullock and Ryan Gosling

Two of the most famous actors of our time, and yes, they totally dated. After meeting on the set of their movie Murder by Numbers, Sandra Bullock and Ryan Gosling were together for almost two years. Looking back on the relationship in a 2011 interview with The Times (per US Weekly), Gosling said that Bullock was one of his “two greatest girlfriends” along with Rachel McAdams.

20 | Katie Holmes and Chris Klein

In the late ‘90s, Katie Holmes was still starring in the teen soap Dawson’s Creek, and she was seeing American Pie star Chris Klein. But in 2005—after five years together and even getting engaged—Holmes and Klein split, and it wasn’t long afterwards that she began her even more high-profile relationship with Tom Cruise.

21 | Brad Pitt and Christina Applegate

Back in 1988, Brad Pitt (still three years away from his breakout role in Thelma & Louise) and Christina Applegate (who was much more famous than him, thanks to her role on Married...With Children) started hanging out, and by 1989, it was all over. During an interview with Andy Cohen on Watch What Happens Live, Applegate confirmed it all came to an end at the MTV VMAs that year, when she ditched Pitt to be with someone else.

22 | Orlando Bloom and Kate Bosworth

Before he was with Miranda Kerr or Katy Perry, Orlando Bloom dated Blue Crush star Kate Bosworth. During an appearance on Watch What Happens Live in 2019, Bosworth admitted that her 2002 to 2006 relationship with Bloom is why she never dated another actor ever again, mostly because the experience—which she said included “girls, like, lifting their shirts up” when she was somewhere with Bloom—just wasn’t for her.

23 | Jennifer Aniston and Tate Donovan

Jennifer Aniston and Tate Donovan dated in real life before their Friends characters had their brief relationship, so the timing of his arc on the show wasn't great.

"The only bummer was Jennifer and I were breaking up at the time," Donovan told Us Weekly in 2018. “And so that was tricky to sort of act, and act like we are just meeting each other, and falling in love, or whatever, interested in each other, when we’re sort of breaking up. That was just tough."

24 | Kim Kardashian and Nick Cannon

Some of Kim Kardashian’s relationships, like her marriages to Kanye West and Kris Humphries, have gotten so many headlines that they've outshined the others, like the time she dated host and actor Nick Cannon. They were together from 2006 to 2007, but it all came to an end when Cannon claimed Kardashian lied to him about that infamous tape.

“If she might have been honest with me I might have tried to hold her down and be like ‘that was before me’ because she is a great girl,” Cannon later told Howard Stern, per The Daily Mail. “She’s actually one of the nicest people you’ll ever meet. But the fact that she lied and told me that there was no tape?”

25 | Milo Ventimiglia and Hayden Panettiere

Despite the fact that Hayden Panettiere is 12 years younger than Milo Ventimiglia, they started dating when they were both starring on the sci-fi show Heroes. Referring to their relationship in a 2017 interview with Mr. Porter, Ventimiglia said he’d never date a costar ever again.

26 | Nicole Kidman and Lenny Kravitz

Interestingly enough, Nicole Kidman and Lenny Kravitz began dating in 2002 when he was her landlord. It wasn’t until years later that Kidman revealed (in a roundabout way) that they’d actually been engaged before they broke up. They’ve friendly ever since, which is a relief, since Kidman would go on to star in Big Little Lies with Kravitz’s daughter, Zoë.

27 | Cara Delevingne and Michelle Rodriguez

We’ve heard a lot about model Cara Delevingne’s former relationship with Pretty Little Liars star Ashley Benson, but lest we forget, she’s also dated Fast and Furious star Michelle Rodriguez. They were together for six months in 2014, and things didn’t end well between them—especially since they've continued to avoid each other in public after they split.

28 | Leonardo DiCaprio and Blake Lively

In 2011, Leonardo DiCaprio and Blake Lively briefly dated while she was still starring in Gossip Girl, reportedly breaking up that October due to the distance between them. That same month, Lively was first spotted with Ryan Reynolds, and we all know how that love story goes.

29 | Jonathan Groff and Zachary Quinto

It’s hard to believe that seven whole years have passed since Frozen star Jonathan Groff and American Horror Story actor Zachary Quinto broke up after only one year together. At the time, sources told Us Weekly that their relationship had just played out, but that didn’t stop fans from being totally heartbroken over it.

30 | Rosario Dawson and Jay-Z

Before Jay-Z and Beyoncé became the music power couple they are today, Jay-Z and Rosario Dawson actually dated. Their relationship was super low0profile, but they dated in 2000, and neither of them has brought it up publicly since.