Celebrities You Forgot Used to Date
Back in 2021, Cher and Val Kilmer reminded us that they dated in the early 1980s. Even with a 14-year age difference, the couple fell “madly in love” and remain friends to this day. “He’s like nobody I’ve ever known,” Cher told People. “He is exasperating and hysterical. Thrilling and funny, and doesn’t do what anyone else does.”
That got us thinking, who else have we forgotten about in the archives of gossip dating history? It’s pretty common for two beautiful actors to hook up while away on set, so that’s often how these unusual couples wound up together in the first place. Do you remember Janet Jackson and Matthew McConaughey and their romance? We sure didn’t — and the two of them seem to have different versions of what exactly went down. And we completely forgot about the Cruz-Cruise relationship (aka Penélope Cruz and Tom Cruise) in the post-Kidman years.
So sit back and reminisce about the couples, who once called might’ve called each other boyfriend and girlfriend… or perhaps it was just a casual time together. Either way, Hollywood rarely forgets because the paparazzi often catch these infamous duos together. Let’s take a look at these long-forgotten famous duos.
A version of this article was originally posted on Aug. 2021.
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Aubrey Plaza & Michael Cera
You might’ve forgotten that Scott Pilgrim vs. the World co-stars Aubrey Plaza and Michael Cera dated because, well, we didn’t know until they were long over.
In a 2016 episode of RuPaul’s podcast, the actress revealed that the two dated for “a year and a half” during and after the movie, per Vanity Fair.
In 2023, Cera revealed they almost eloped in Vegas. “Well, we were driving through Vegas, and we almost just spontaneously took a detour and got married,” he told Rolling Stone. “I think the idea was to then get a divorce right away, so we could call each other “my ex-husband” and “my ex-wife” at like … 20.”
Matthew Morrison & Chrishell Stause
Though it may be hard to believe, Glee star Matthew Morrison not only dated but was once engaged to Selling Sunset star Chrishell Stause. They started dating back in 2006 and got engaged a year later, per People. But, not long after he popped the question, the pair called it quits.
“I didn’t do it for the right reasons,” Morrison told Cosmopolitan of the engagement in 2013, per Page Six. “We’d been going out for a year or so. … I was thinking, ‘This is the age when I should probably start having kids, so this is what I should do.’ But after I did it, I immediately felt in my heart it wasn’t right. My instant thought was, ‘What did you just do?’. ”
Years later, Stause even called out Morrison on her Netflix show, referring to him as a “d–.” “Yeah you can Google that! You were a d—! Sorry!” Stause said.
Matthew Morrison & Kristen Bell
Speaking of Morrison, Mr. Shue also dated fellow actor Kristen Bell.
“I actually went to college with Matty Morrison,” she told UsWeekly. “We actually dated very briefly, so I’ll have to say maybe Matt Morrison is my favorite part of Glee for various reasons.”
Zachary Quinto & Jonathan Groff
Star Trek star Zachary Quinto once dated recent Tony winner Jonathan Groff. According to Us Weekly, Quinto confirmed their relationship in an interview with Out in 2012. “I’m incredibly happy, I’m incredibly lucky,” the actor said.
A year later, however, the pair called it quits. “It just ran its course,” the insider noted at the time. “Zach has been out and about and he seems fine.”
Quinto and Groff have remained close friends ever since.
Tiger Woods & LeAnn Rimes
When LeAnn Rimes was just 19 years old, she reportedly went out with golfer Tiger Woods.
“They hooked up and everything,” a source told Us Weekly. “Tiger was really into her. He likes those blondes!”
After those few dates, however, Rimes’ dad got word of their relationship and protested immediately. After all, Woods was seven years older than her.
“Then her dad almost had a heart attack,” the source said. “And he made her stop seeing Tiger.”
Joshua Jackson & Rosario Dawson
Not much is known about Joshua Jackson and Rosario Dawson’s old relationship, but we do know that they were together for around one year, specifically from 2002 to 2003.
Sandra Bullock & Matthew McConaughey
Remember when former co-stars Sandra Bullock and Matthew McConaughey dated from 1996 to 1998?! Many don’t, and for those that do, don’t worry because they’re still buddies to this day!
Tom Cruise & Sofía Vergara
Back in 2005, Will Smith introduced Sofía Vergara to Tom Cruise at a pre-Oscar party, and soon after, Cruise called up Vergara to invite her to an upcoming party. They hit it off immediately, but split up soon after for one of two reasons: some claim Vergara left him because he tried to convert her to Scientology, and others claim he left to be with Katie Holmes.
Mila Kunis & Macaulay Culkin
A lot of people either forgot or never knew that Mila Kunis and Macaulay Culkin dated for nine years. Yes, you read that right: nine years! The pair started dating in 2002 and kept their relationship incredibly private from the public. However, it was reported that had a “horrible” breakup, so bad to the point that they cut ties altogether.
In an interview with Women’s Health back in 2009, she said, “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.”
Val Kilmer & Cher
We love that Cher has never had any qualms about dating someone younger than her. Val Kilmer met the legend at her birthday party one year and there was instant chemistry. These two loved hard and they fought hard because they were both used to being the dominant personality in the relationship.
“We had unbelievable times and then put up with some times when they weren’t [that way] because we were both Alpha males,” she said to People. “We were both individuals and neither of us was going to give up on that.”
The couple broke up in 1984 after two years of dating.
Tom Cruise & Cher
We know Cher loves a younger man, and, at the beginning of his career in 1985, Tom Cruise dated the Hollywood icon. And let’s just say she had some pretty spectacular things to say about the Mission Impossible star when Andy Cohen asked how high Cruise ranked on her lovers’ list.
“He was in the top five. It’s not a long list, just a good list,” Cher revealed. “It could have been a great big romance, because I was crazy for him.”
Penélope Cruz & Tom Cruise
Tom Cruise’s relationship with Penélope Cruz came on the heels of his breakup with Nicole Kidman, so there were a lot of eyeballs on her when she came into the picture. The two met on the set of Vanilla Sky and they made their relationship red carpet official in August 2001.
“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,” she said to The Telegraph, years after they broke up. “It’s always a mystery. You can’t plan those things.”
The couple split in 2004.
Matthew McConaughey & Janet Jackson
Alright, alright, alright, this couple is a he-said, she-said story. Matthew McConaughey and Janet Jackson met at the 2002 Grammy Awards and might have gone on a date — it depends on who you talk to.
“I met her at the Grammys and found her to be a very, very sweet lady. 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 WENN. “That’s about all there is right now.”
But if you ask Jackson, it was a little bit more. “I guess we did [date]. He is such a great guy and a sweetheart,” she said to the Telegraph, via Marie Claire. “It was just for a minute, that’s why I’m so hesitant to mention it.”
Lenny Kravitz & Nicole Kidman
Believe it or not, Nicole Kidman, now happily married to Keith Urban, was once upon a time engaged to Lenny Kravitz. He was her first serious relationship after divorcing Tom Cruise.
And life always comes full circle because Kidman wound up working with her almost-stepdaughter, Zo? Kravitz, on Big Little Lies. “Well, I knew Zo? because I was engaged to her father,” she told The Edit, via People. “It’s all in the family! I love Lenny; he’s a great guy.”
Michael Jackson & Madonna
While we aren’t sure if this was a relationship or a one-night dating situation, Michael Jackson and Madonna were the most talked about couple at the 1991 Oscars. For the occasion, she was slated to sing the nominated song “Sooner or Later” from the movie Dick Tracy, but she had no date. That’s when Jackson swooped in.
“Michael was like, ‘Well, who are you gonna go with?’ I looked at him and said, ‘I don’t know. You wanna go?'” Madonna told VH1. “And he said, ‘Yeah, that’d be great.’ And then, yes, he took me home. You wanna know what happened after that? I’m not gonna tell you.” The pop star confirmed to James Corden that a kiss did happen that night — and maybe something more.
Brad Pitt & Christina Applegate
Christina Applegate and Brad Pitt attended the 1989 MTV Music Awards together, but the Dead to Me star left the show with someone else that night. Over the years, she’s refuses to reveal who it was, but told Andy Cohen on Watch What Happens Live that the guy she left Pitt for was “known to the public.” Pitt was jilted.
Julia Roberts & Matthew Perry
This is one relationship we wished we had red carpet-photos to look back on. The late Matthew Perry was set up with America’s Sweetheart Julia Roberts after she starred in their Super Bowl episode in 1996.
They were spotted having romantic dinners around the Hollywood area after the episode aired, but the only juicy scoop we got is that the couple went on “a few dates” from Perry’s publicist and “a couple of dates” from Roberts’ team, per People. It fizzled out after that, but oh, what could have been.
In his memoir, Friends, Lovers, and the Big Terrible Thing: A Memoir, Perry opened up about why they split.
“Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me,” he explained. “Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”
Jessica Biel & Chris Evans
Before Jessica Biel ever met Justin Timberlake and before Chris Evans hit it big as Captain America, this cute couple dated — and it was serious. Biel told Cosmopolitan that they often discussed getting engaged. “We both
want to be married, and we both want to have children,” she revealed. “But we’re not engaged, so the rumors are false… so far.”
The couple dated from 2001 until 2006.
Fergie & Justin Timberlake
During his *NSYNC (and pre-Jessica Biel) days, Justin Timberlake dated Fergie because, well, it was convenient for the two of them at the time. Fergie even called him “Mr. Right Now” — oof.
“One of my good friends was dating J.C. Chasez, and so we’d all hang out with *NSYNC. Justin and I would go out together and have fun and make out,” she said to Cosmopolitan, via Us Weekly. “We went to Hawaii together, but we were never serious.”
Jake Gyllenhaal & Kirsten Dunst
Jake Gyllenhaal had his sister, Maggie Gyllenhaal, to thank for setting him up with her Mona Lisa Smile co-star, Kirsten Dunst. The couple began dating in 2002 and were seen at every red carpet together. They broke up two years later for a simple reason — Dunst considered herself “an out-on-the-town girl” and her ex was “a stay-at-home boy,” per News of the World.
Helen Mirren & Liam Neeson
We were today-years-old when we found out Helen Mirren and Liam Neeson dated for quite a while after meeting on the set of Excalibur in 1980. They recounted their sweet romance on The Graham Norton Show in 2018.
“We didn’t [just] date, we lived together for four years,” she said on the show. “We were a serious item for a while. Lucky me!” How sweet!
Heather Graham & Matthew Perry
Heather Graham and Matthew Perry had a short-lived fling in 2003, according to E! News.
David Arquette & Drew Barrymore
Scream co-stars David Arquette and Drew Barrymore dated briefly in 1991, despite Barrymore denying it. “We also dated, but she denied it on Howard Stern,” Arquette said in an episode of PeopleTV’s Couch Surfing. “But, we dated, Drew!”
Matt Damon & Winona Ryder
After being introduced to one another by Gwyneth Paltrow, Matt Damon and Winona Ryder dated for three years, from 1997 to 2000. And they still remain on good terms to this day.
Joaquin Phoenix & Liv Tyler
Joaquin Phoenix and Liv Tyler were young lovebirds, dating for three years when they were only 18 and 20. Despite their breakup, Tyler told Elle, “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.”
Jenna Dewan & Justin Timberlake
Jenna Dewan and Justin Timberlake dated very briefly back in 2002 when Dewan was one of his backup dancers. They dated soon after Timberlake and Britney Spears broke up, telling Glamour that she wasn’t the rebound, saying, “We dated, not that long. We were like friends…that dated. I was not the rebound! I was very clear not to be [that].”
Jennifer Aniston & Paul Rudd
Jennifer Aniston and Paul Rudd dated! (Don’t tell Phoebe, Friends fans!) They reportedly dated for a brief period of time while filming The Object of My Affection together, and have stayed friends throughout the years.
Jared Leto & Cameron Diaz
Jared Leto and Cameron Diaz began dating in 1999, trying to keep a low profile (and failing after word quickly got out). They split up after four years together and haven’t talked about each other since.
Shia LaBeouf & Hilary Duff
Honestly, Shia LaBeouf and Hilary Duff defined our childhoods, so it makes sense. In a previous interview, LaBeouf described their one-date affair as “probably the worst date either of us have ever had.”
Brooke Shields & Nicolas Cage
Again, not much is known about Brooke Shields and Nicolas Cage’s low-key and brief romance. All we do know is that it happened, and they honestly looked pretty cute together at the premiere of Moonstruck.
Rosario Dawson & Jay-Z
We’re serious: Rosario Dawson and Jay-Z dated back in the early 2000s, and we all somehow forgot about that. Not much is known about their relationship because they were super private then, and neither has brought it up since.
Leonardo DiCaprio & Blake Lively
Right before Blake Lively and Ryan Reynolds got together, she was briefly linked with Leonardo DiCaprio a few months prior in 2011.
Cara Delevingne & Michelle Rodriguez
Back in 2014, Cara Delevingne and Fast and Furious star Michelle Rodriguez dated for six months. It was confirmed that they were dating after their PDA-filled, public appearance at a basketball game in New York.
Kim Kardashian & Nick Cannon
Does anyone remember this? Kim Kardashian and Nick Cannon dated briefly for less than six months in the early 2000s, and they allegedly split after Kim’s sex tape was leaked.
Orlando Bloom & Kate Bosworth
Back in 2002, Orlando Bloom and Kate Bosworth were the IT couple, dating for four years until their eventual split in 2006. The A-listers met while filming a Gap commercial, and Bosworth called the breakup her “first big heartbreak.”
“You know when you put all your chips into something, then it disappears? [The breakup] sent me into such pain, I think I had actual vertigo. I was like, ‘Is this my new reality? Will anything be normal again,'” she said to US Magazine. “Then one day you wake up, and you think, OK, I’ll never be the same, but I’ll survive, and I’ll grow from it.”
January Jones & Ashton Kutcher
Mad Men meets That 70s Show? We’re intrigued. But does anyone remember when January Jones and Ashton Kutcher dated from 1998 to 2001? It was alleged they split up because of Kutcher’s jealousy of Jones’ friend Bruce Willis.
Emily Blunt & Michael Bublé
In case you didn’t know, Emily Blunt and Michael Bublé dated for three years, from 2005 to 2008. Rumors circulated that he cheated, but he denied those quickly, telling Entertainment Tonight, “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.”
Kate Hudson & Alex Rodriguez
Unlikely pair Kate Hudson and Alex Rodriguez had a brief relationship back in 2009, but it fizzled out quite quickly due to jealousy and their high-profile relationship, per Nicki Swift.
Elizabeth Taylor & Colin Farrell
That’s right, Elizabeth Taylor and Colin Farrell had a fling. Back in 2013, Farrel revealed to the world that they were very close for a couple of years, leading to a brief affair, despite the 40-year age difference.
Robert Downey Jr. & Sarah Jessica Parker
Robert Downey Jr. and Sarah Jessica Parker dated for around seven years, from 1984 to 1991, to be exact. While they were pretty lowkey, it became public knowledge that Downey’s drug and alcohol abuse led to their breakup. He told Parade in 2008, “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.”
Elon Musk & Talulah Riley
Elon Musk and Pride and Prejudice star Talulah Riley were an odd couple, to say the least. They started dating in 2008, got married in 2010, and divorced two years later. But then they remarried in 2013 and got divorced in 2016. Yet somehow, everyone forgets about this pair.
Seth MacFarlane & Emilia Clarke
Who remembers this romance: Family Guy creator Seth MacFarlane and Emilia Clarke? Yup, it happened, and it happened for around a year from 2012 to 2013. Despite keeping their relationship lowkey, they split due to long distance (and potentially their 14-year age gap).
Tyra Banks & Drake
Okay, so this one may be a bit of a stretch because Tyra Banks and Drake only went on one date. But that’s still dating! And let’s face it, no one remembers this match-up.
Drake said on an episode of Ellen: “It was just one date. 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.”
Salma Hayek & Edward Norton
Salma Hayek and Edward Norton dated from 1999 to 2003 after the two were set up by their chiropractor. While they were private, they did make headlines when Norton helped Hayek produce the film Frida.
Alanis Morissette & Ryan Reynolds
Get ready for a relationship everyone forgot about: Alanis Morissette and Ryan Reynolds. The two started dating in 2002 after meeting at Drew Barrymore’s birthday party. They got engaged two years later in 2004, but called it quits in 2007. Morisette actually wrote her album Flavors of Entanglement, all about their love and breakup!
