Hold up – they dated?
It’s always fun to look back at celebrity couple pairings you had no idea were once romantically involved. But alas, since tinseltown is so small, there are many famous couples that most people didn’t even realize existed in the first place.
Here are some of the oddest star-studded celebrity couple duos who you would’ve never guessed were once in serious relationships with each other. (We’re looking at you, Sarah Jessica Parker and Robert Downey Jr.!)
Sarah Jessica Parker and Robert Downey Jr.
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Many fans of the Sex and the City star and the Iron Man actor don’t realize these celebs were together for eight long years. The pair were in a committed relationship starting at the age of 18, when they met on the set of the 1984 film, Firstborn. Shortly after meeting, they decided to live together, and even bought a house in an art deco mansion which once belonged to Charlie Chaplin.
The pair were committed to each other and deeply in love throughout their breakout years in Hollywood. According to The Avengers star’s father in a 1985 interview with People Magazine, Sarah Jessica Parker posed as an amazing influence for Robert Downey Jr. “I thank God for Sarah Jessica Parker,” Robert Downey Sr. told the magazine. “Without her, Robert would go at 100 miles an hour into a brick wall. They’re very sweet together. He might become a gentleman as a result of this.”
Unfortunately, Downey Jr.’s addiction to drugs and alcohol ultimately broke off their nearly decade-long relationship. While sitting down with Parade (Via InStyle), the actor revealed, “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.”
In 2024, Downey Jr. celebrated 15 years of sobriety.
Paul Rudd and Jennifer Aniston
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Just what would Phoebe Buffet have to say about this?? According to Jennifer Aniston, she and her former Friends co-star Paul Rudd briefly dated when they were “like 12 years old” (per Yahoo!)
Although they didn’t last long as a couple, the pair seem to be great friends to this day.
They even starred alongside each other as a couple in the 2012 film, Wanderlust. And in 2024, while celebrating the Ant-Man star’s 50th birthday, the Friends star made a heartwarming post via her Instagram story. Alongside a picture of the two in their movie Wunderlust, the actress wrote, “Happy Birthday Paul Rudd. I love you, you ageless freak!”
Matthew Broderick and Jennifer Grey
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Matthew Broderick and Jennifer Grey famously played brother and sister in the John Hughes classic, Ferris Bueller’s Day Off. This little tidbit made it all the more strange that behind the scenes, Broderick and Grey were engaging in a secret romance.
“Matthew just felt like my guy,” Grey revealed in her memoir. She added, “He felt like home.”
Chris Noth and Kristen Davis
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Carrie Bradshaw is quaking in her Manolo Blahniks right now, because according to rumors, Chris Noth (aka Mr. Big) and Kristen Davis (Charlotte York-Goldenblatt) were once an item.
Despite Noth being romantically involved with Sarah Jessica Parker’s character on Sex and the City, behind the scenes, Noth and Davis were often seen cozied up together in a way that certainly didn’t look platonic.
While there’s no official reports on their relationship history, these pictures say a thousand words.
Julia Roberts and Matthew Perry
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Can you believe Julia Roberts and Matthew Perry were once an item? In the Friends star’s recently published memoir, the actor dished on his brief yet significant romance with the Notting Hill actress.
According to Perry, Roberts was offered an opportunity to guest star on an episode of Friends. Yet she would only do it on one condition: If, and only if, she was in a storyline with Chandler Bing. Needless to say, Perry was insanely flattered. As a result, he sent Roberts a dozen roses. The Pretty Woman actress quickly became enamored with Perry’s goofy sense of humor, and it wasn’t long before the two became romantically involved.
But unfortunately, the Friends alum ended up breaking things off with Roberts just months into their relationship, since he believed he “wasn’t good enough” for her.
“Dating Julia Roberts had been too much for me,” Perry wrote in his memoir (Per Page Six.) “I had been constantly certain that she was going to break up with me… 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,”
To add to the tragedy, Matthew Perry passed away on the same day as Julia Roberts’ birthday.
Demi Moore and Emilio Estevez
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Back in the 1980s, The Substance actress and The Breakfast Club star were engaged. The pair met while starring in Joel Schumacher’s hit movie, St. Elmo’s Fire. Despite falling head over heels for one another, the pair quickly called off the engagement when Moore discovered Estevez was cheating on her. According to Demi Moore’s memoir, Inside Out, The wedding was officially called off when the Ghost star discovered Estevez had gotten his ex-girlfriend pregnant during their engagement. Not exactly what we’d call “relationship goals”!
Frank Sinatra and Marilyn Monroe
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Taking it way back, many people are unaware that crooner Frank Sinatra and Hollywood icon Marilyn Monroe were once romantically linked. Although the two were never reported as an official celebrity couple, it’s been widely documented that the pair shared a romantic relationship. But despite not relying on labels, their dynamic was far from casual. According to some sources, the “New York, New York” singer was deeply in love with Monroe, and even planned on marrying her (per The Daily Mail.)
Which of these forgotten celebrity couples do you love the most?
- Wait… THEY Dated?! 9 Celebrity Couples You Totally Forgot About - April 23, 2025
- Inside Matthew Perry and Julia Roberts’ Tragic Romance - April 22, 2025
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