Whitney Port Claims She Was ‘Too Nervous To Have ‘One Night Stand’ With Leonardo DiCaprio

While she’s happily married now, Whitney Port is spilling the tea on a former fling.

During the latest episode of her “With Whit” podcast, “The Hills” alum, 34, claims to have “turned down” a one night stand with Leonardo DiCaprio nearly 10 years ago.

“The Hills: New Beginnings” star sat down with her “best friend of life” Andrea Cuttler for the episode where the two recalled their wild night where they ran into Rihanna and DiCaprio.

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“I have been dying to tell people this story for ages,” Port began. “I feel like whenever I tell it to friends, no one believes me.”

As she explained, Port and Cuttler went over to chat with Rihanna when DiCaprio came over to introduce himself to Port, claiming to be a huge fan of “The City”, Port’s “The Hills” spinoff.

“And then Leo comes up to you to also … insinuated that, like, he had missed the week priors episode,” Cuttler recalled. “And you’re like, is he telling me that he watches ‘The City’? This is very confusing, but also incredible.”

After “a phone number exchange” the pair joined DiCaprio and his friends at another club.

“I remember dancing alone on the dance floor because you were in the corner talking to him and I didn’t want to intrude, but also like couldn’t leave,” Cuttler added.

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According to Port, they had a “bbm relationship for like six months” before meeting up again in Los Angeles.

“He invited me out to Teddy’s and he invited me back over to his house and I said no,” Port explained. “I was too nervous. I had never had a one-night stand. I didn’t want to be with him alone.”

She added, “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. If you didn’t think I was cool, now you probably do.”

Port later married Tim Rosenman in 2015 and the couple have a son together, Sonny.

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