Whitney Port Says She Had a 'Text Relationship' With Leonardo DiCaprio for Six Months

Whitney Port is once again opening up about talking to Hollywood playboy Leonardo DiCaprio. 

While at the Dear Media IRL summit, The Hills alum revealed that she and DiCaprio once crossed paths and he gave her his number. 

"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," says Port. "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."

While having a good time, the unthinkable happened, Port dropped her cell phone in a puddle of water. 

"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.'"

Port recalls doing what so many of us have done before, "Then I stuck it in rice and it worked."

The reality star says she opened up to the executive producer of The City about meeting DiCaprio and feels they then leaked it to the press. 

"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."

In August 2019, The Hills: New Beginnings star chatted with her best friend, Andrea Cuttler, on her With Whit podcast, where she revealed that she almost had a one-night stand with DiCaprio.

"I have been dying to tell people this story for ages! I feel like whenever I tell it to friends, no one believes me," Port excitedly said, before explaining that in 2009, she and Cuttler were at New York City's Avenue club when -- after meeting Rihanna -- DiCaprio came up to her and they exchanged phone numbers.

Port then said that she and DiCaprio texted for six months, only reuniting once during that time.

"He invited me out to Teddy's and he invited me back over to his house, and I said no," she revealed. "I was too nervous. I had never had a one-night stand. I didn't want to be with him alone."

"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," Port said.

As for DiCaprio, last month he once again fueled romance rumors when he was spotted hanging out with model Irina Shayk -- but a source tells ET that this is not a romantic relationship.

The 48-year-old actor and the 37-year-old model were seen together at the Neon Carnival during the first weekend of the 2023 Coachella Valley Music and Arts Festival in Indio, California. They were joined by a few of their famous friends, including Stella Maxwell and DiCaprio's longtime pal, Tobey Maguire.

The next day, both Shayk and DiCaprio were also at Coachella's Revolve Festival, but an eyewitness tells ET that "they hung out in separate cabanas and not with each other."

"Irina was with her publicist and friends and Leo was with friends and some girls. Both of them had a great time doing their own thing," the eyewitness notes.

Also at the Revolve Festival the day before was DiCaprio's ex-girlfriend, 25-year-old actress Camila Morrone.  

"Camila and Leo were at Revolve Festival at the same time. Camila arrived before Leo did. She was hanging out with Suki Waterhouse and Emma Roberts and seemed to be having a good time. She was dancing a lot in her cabana," an eyewitness tells ET of the Daisy Jones & The Six star, who dated DiCaprio for four years before their split in August 2022. "Leo was in a separate cabana with Tobey Maguire and some guy friends and they were hanging with a few girls. He kept it low-key and also looked like he was having fun."

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