• News
  • Film and TV
  • Music
  • Tech
  • Features
  • Celebrity
  • Politics
  • Weird
  • Community
  • Advertise
  • Terms
  • Privacy & Cookies
  • LADbible Group
  • LADbible
  • SPORTbible
  • GAMINGbible
  • Tyla
  • UNILAD Tech
  • FOODbible
  • License Our Content
  • About Us & Contact
  • Jobs
  • Latest
  • Topics A-Z
  • Authors
Facebook
Instagram
X
Threads
TikTok
YouTube
Submit Your Content
Whitney Port reveals she had a six month ‘text relationship’ with Leonardo DiCaprio

Home> Celebrity

Published 14:47 13 May 2023 GMT+1

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.

Rashi Agarwal

Rashi Agarwal

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.

Advert

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.

Advert

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

Advert

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.

Advert

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.
Whitneyeveport

Advert

"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.

Featured Image Credit: AFF / Associated Press / Alamy Stock Photo

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

Rashi Agarwal
Rashi Agarwal

Advert

Advert

Advert

Choose your content:

17 mins ago
2 hours ago
20 hours ago
21 hours ago
  • Jeenah Moon/Bloomberg via Getty Images/Laura Cavanaugh/Getty Images
    17 mins ago

    Epstein accuser Virginia Giuffre's bombshell claim Ghislaine Maxwell boasted about 'performing sex act' on major Hollywood A-lister

    Virginia Giuffre detailed the alleged encounter in her newly-released memoir

    Celebrity
  • IMPAULSIVE/YouTube
    2 hours ago

    How Liam Payne reacted to interview that's left Louis Tomlinson vowing to 'f**king forever despise' one celebrity

    An infamous interview left Payne's bandmate furious

    Celebrity
  • Justin E Palmer/Getty
    20 hours ago

    Louis Tomlinson reveals the one celebrity he will ‘f***ing forever despise’ because of Liam Payne interview

    Tomlinson expressed his animosity towards this particular influencer

    Celebrity
  • Kyle and Jackie O Show
    21 hours ago

    Hugh Hefner's ex-girlfriend Kendra Wilkinson detailed what she saw during Diddy's infamous parties

    The Girls Next Door star moved into the Playboy Mansion with Hefner after meeting at his 78th birthday party in 2004

    Celebrity
  • Leonardo DiCaprio reveals the one career move that was he says was his biggest 'regret'
  • Margot Robbie secured role in Wolf of Wall Street with one bold move on Leonardo DiCaprio
  • Leonardo DiCaprio has a five word response for lifelong health battle he is still fighting
  • Netflix is adding 94% rated Leonardo DiCaprio movie labeled ‘the GOAT of cinema’