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Whitney Port reveals she had a six month ‘text relationship’ with Leonardo DiCaprio
Featured Image Credit: AFF / Associated Press / Alamy Stock Photo

Whitney Port reveals she had a six month ‘text relationship’ with Leonardo DiCaprio

Port has previously spoken about a six-month fling with DiCaprio and 'missing out' on a one-night stand with the star.

Whitney Port revealed that she had a six-month 'text relationship' with Leonardo DiCaprio.

Known for being in relationships with women half his age, DiCaprio was half-involved this time but unlike his other flings, this one never made it to the papers.

The Hills star spoke largely about how DiCaprio and she came in contact, exchanged numbers, and remained in touch for over six months.

She told all about the not-so-brief meet at the Dear Media IRL summit and said: "I've talked about this before and on my podcast but I ran into Leonardo DiCaprio at a nightclub and we proceeded to exchange numbers and had like a text relationship for six months.

Leonardo Di Caprio dated Whitney Port for six-months but over texts.
Insidefoto di andrea staccioli / Alamy Stock Photo

"We were at the nightclub and he had someone call me over. I immediately called my mom and stepped outside of the club.

"And then he was like, 'Come over. We’re going to the one next door too.' And I went with my best friend."

However, as fate would have it, Port mistakenly dropped her phone in a pool of water and feared not being able to receive Leo's text.

She said: "It wouldn’t turn on and I was freaking out because I was like, 'Leo’s gonna text me and I'm never gonna get it.'"

"Then I stuck it in rice and it worked!"

Port told The City's executive producer about the brief meet in confidence, but he double-played and leaked it to the media.

DiCaprio is still one of Hollywood’s most in-demand stars
DiCaprio is still one of Hollywood’s most in-demand stars

After which, to Port's disappointment, she never received a text back Leo.

She added: "I think he leaked it to the press and then [Leo] never texted me back…It was not an emoji time, we were on Blackberries."

It gets more interesting as we read, Port further discussed with her best friend, Andrea Cuttler, about having the chance for a 'one-night stand' with DiCaprio.

During her night out at New York City's Avenue Club in 2009, DiCaprio approached her and they exchanged numbers only to be invited to his place later on.

She explained all on an episode of the With Whit podcast in 2019, saying: "I have been dying to tell people this story for ages! I feel like whenever I tell it to friends, no one believes me.

"He invited me out to Teddy's and he invited me back over to his house, and I said no.

"I was too nervous. I had never had a one-night stand. I didn't want to be with him alone."

Port told The City's executive producer but leaked it to the media.

"I was way too nervous to do it and then I lost my chance and it’s really one of my bigger regrets in life," she added. "If you didn't think I was cool, now you probably do."

"I wonder if he would remember that we had this relationship."

DiCaprio is currently known to be dating 37-year-old model Irina Shayk, who was spotted with him at the 2023 Coachella Valley Music and Arts Festival in Indio, California.

The Titanic star has been criticised for his 'creepy' dating patterns by comedian Katherine Ryan who took to social media to speak about his romances.

Topics: Film and TV, Leonardo DiCaprio, Sex and Relationships