“He tried back in the day”: Leonardo DiCaprio Has Dated Many Supermodels But He Was Rejected by Brad Pitt and Ben Affleck’s Ex-girlfriend

"He tried back in the day": Leonardo DiCaprio Has Dated Many Supermodels But He Was Rejected by Brad Pitt and Ben Affleck's Ex-girlfriend
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Hollywood heartthrob Leonardo DiCaprio, famously known for his appearance as Jack Dawson in James Cameron’s Titanic, 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. 

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Leonardo DiCaprio
Leonardo DiCaprio

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

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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 epic Titanic, alongside Kate Winslet, the actor turned into a household name and started engaging in high-profile relationships. 

Leonardo DiCaprio
DiCaprio once tried to pursue Brad Pitt’s ex

However, despite dating several models throughout his decades-long career, Leonardo DiCaprio failed 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. 

Leonardo DiCaprio
19-year-old Leonardo DiCaprio took a major interest in Gwyneth Paltrow

Having high-profile relationships with Ben Affleck and Brad Pitt during her early years in Hollywood, Gwyneth Paltrow wasn’t thoroughly impressed with DiCaprio. Appearing in Alex Cooper’s Call Her Daddy podcast, the actress revealed how the Shutter Island actor tried to impress her, but she wasn’t quite interested. 

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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 and Brad Pitt, Gwyneth Paltrow told Alex Cooper how Leonardo DiCaprio once took an interest in her. During her appearance on Call Her Daddy podcast, 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.” 

Gwyneth Paltrow
Gwyneth Paltrow spoke about her romance with Brad Pitt and Ben Affleck

Stating how her years in the entertainment industry brought her close to DiCaprio, Gwyneth Paltrow mentioned how hard the actor tried to impress her. However, she never gave in. Apparently, the Titanic actor even tried to make out with her, but Paltrow simply refused to engage with him. 

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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.” 

Gwyneth Paltrow
Paltrow never considered DiCaprio as boyfriend material

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

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Written by Krittika Mukherjee

Articles Published: 1458

Krittika is a News Writer at FandomWire with 2 years of prior experience in lifestyle and web content writing. With her previous works available on HubPages and Medium, she has woven over 1000 stories with us, about fan-favorite actors, movies, and shows. Post-graduate in Journalism and Honors-graduate in English Literature, when this art enthusiast isn't crafting your next favorite article, she finds her escapism in coffee, fiction, and the Wizarding World.