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Hollywood heartthrob Leonardo DiCaprio, famously known for his appearance as Jack Dawson in James Cameron’sTitanic, is making notorious headlines for his unconventional love life. However, despite dating several young models, for a long, the actor once failed to pursue an iconic actress with his charm and good looks.

Despite trying to seduce the actress, Leonardo DiCaprio failed to get her attention, during his initial years in the industry. Apparently, the actress wasn’t interested in the megastar at that time. Well, the iconic woman who was immune to DiCaprio’s charm was none other than Brad Pitt and Ben Affleck’s ex-girlfriend.
Also read:“Chris was staunchly against that”: Christopher Nolan Narrowly Avoided The Same WB Mistake That Doomed Zack Snyder’s DCEU

Ben Affleck’s Ex-Girlfriend Turned Down Leonardo DiCaprio
Rising to fame during the 90s, young Leonardo DiCaprio was a major Hollywood heartthrob due to his incredible persona, charm, and good looks. Further, following his appearance in the romantic epicTitanic, alongside Kate Winslet, the actor turned into a household name and started engaging in high-profile relationships.
However, despite dating several models throughout his decades-long career,Leonardo DiCapriofailed to seduce one iconic Hollywood actress, during his early years. Apparently, when the actor was around 19, he tried to pursue Gwyneth Paltrow as he developed an interest in her. But, unfortunately, the actress turned him down.

Having high-profile relationships withBen Affleckand Brad Pitt during her early years in Hollywood, Gwyneth Paltrow wasn’t thoroughly impressed with DiCaprio. Appearing in Alex Cooper’sCall Her Daddypodcast, the actress revealed how theShutter Islandactor tried to impress her, but she wasn’t quite interested.
Also read:“I should have gone on probably to do…”: The $50M Liam Neeson Movie Martin Scorsese Regrets Turning Down for Leonardo DiCaprio’s Shutter Island

Leonardo DiCaprio Wasn’t a Boyfriend Material For Brad Pitt’s Ex
Discussing her romantic affairs with her ex-boyfriends, Ben Affleck andBrad Pitt, Gwyneth Paltrow told Alex Cooper how Leonardo DiCaprio once took an interest in her. During her appearance onCall Her Daddypodcast, Paltrow mentioned how she initially liked to explore her preferences in men, and that’s when she caught DiCaprio’s attention.
“I think I was really a kid, like, really more so than a lot of 22 or 23 or 24-year-olds I would meet now. I really had not explored who I was, what was important to me, what my boundaries were. Anything like that.”

Stating how her years in the entertainment industry brought her close to DiCaprio,Gwyneth Paltrowmentioned how hard the actor tried to impress her. However, she never gave in. Apparently, theTitanicactor even tried to make out with her, but Paltrow simply refused to engage with him.
“Nope, never made out with Leo. He tried back in the day. But he was already, like, you know, he was very loose with the goods from when he was 19.”
Confessing how she never felt like Leonardo DiCaprio was boyfriend material, Paltrow admitted rejecting the infamous actor. Later on, both stars went on to date different celebrities, respectively, and made flashy headlines for their high-profile affairs.
Read more:“No, I was in Avengers”: Is Fame Getting to Her? Gwyneth Paltrow Forgot a Marvel Movie She Herself Starred In That Paid Robert Downey Jr $1M Per Minute
Source:Call Her Daddy
Krittika Mukherjee
Senior Writer
Articles Published :3219
Krittika Mukherjee is a Senior Entertainment Writer at FandomWire, majorly focusing on films, TV shows, and celebrity news with over 3,000 articles published. With an educational background in Journalism, and a keen interest in filmmaking, Krittika blends factual precision with creative flair, when crafting her editorials, or dissecting fan theories.Her coverage often includes news and analyses of critically acclaimed films, celebrity news, and franchises like the Wizarding World, LOTR, DC, and MCU—particularly Harry Potter, Fantastic Beasts, Superheroes, and fan theories. As a Wizarding World aficionado, Krittika has spent countless hours exploring hidden backstories, unadapted book moments, spells, and trivias surrounding J.K. Rowling’s lore.An imaginative writer with a way with words, Krittika has worked as an entertainment journalist for the past two years and a web content writer for a year. She brought her experience and expertise to FandomWire to pursue her desire for sipping coffee while dissecting films and tracking celebrity drama.