How Whitney Port narrowly missed being part of

LOS ANGELES, CALIFORNIA: Whitney Port, Lauren Conrad’s friend and coworker on ‘The Hills,’ wasn’t the most well-known person, but she was most likely the most envious. She was well-liked by everyone, talented in all areas, and even earned her own spin-off, ‘The City’. Men, including Leonardo DiCaprio, reportedly wanted to be with her and girls wanted to be like her as well.


Leonardo DiCaprio, who is notorious for dating women half his age, participated in this relationship to a lesser extent than usual but, unlike his earlier flings, this was never reported in the media. ‘The Hills’ star discussed extensively how she met DiCaprio, how they exchanged phone numbers, and how they kept in touch for more than six months.


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‘Had a text relationship for six months’

In 2009, DiCaprio approached her after her night out at New York City’s Avenue Club. They exchanged phone numbers, and later, he invited her to his home. At the ‘Dear Media IRL’ meeting, the former cast member of ‘The Hills’ detailed their lengthy encounter and said: “I ran into Leonardo DiCaprio at a nightclub and we proceeded to exchange numbers and had, like, a text relationship for six months…and that was really really fun,” per GLAMOUR. “We were at the nightclub and he had someone call me over. I immediately called my mom and stepped outside of the club,” Port went on to say.


The ‘Entourage’ actor continued: “And then he was like, ‘Come over. We’re going to the one next door too.’ And I went with my best friend. I ended up that night dropping my cell phone in a puddle of water, and 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.’ And then I stuck it in rice and it worked.”


‘The Hills: New Beginnings’ star opened up about nearly having a one-night stand with DiCaprio in an interview with her best friend Andrea Cuttler on the ‘With Whit’ podcast in August 2019. Port continued by revealing that she and DiCaprio only met up once during their six-month text relationship, as per ET Online.

What happened between Whitney and Leo?

Despite the phone issues, Port said that their relationship ended after she told a TV producer about it. ‘The City’s producer double-played and leaked it to the media. Port said: “I told our executive producer about it, because we were friends, and then I think he leaked it to the press and then [DiCaprio] never texted me back. I wonder if he would remember that we had this relationship.”


Regarding DiCaprio, he once again stoked romance speculations when he was seen partying with model Irina Shayk last month, but a source tells ET that they are not romantically involved. During the opening weekend of the 2023 Coachella Valley Music and Arts Festival in Indio, California, the 48-year-old actor and the 37-year-old model were spotted together at the Neon Carnival.

Leonardo DiCaprio attends the EE British Academy Film Awards at the Royal Opera House on February 14, 2016 in London, England.
Leonardo DiCaprio attends the EE British Academy Film Awards at the Royal Opera House on February 14, 2016 in London, England (Gareth Cattermole/Getty Images)

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