'The Hills' Star Whitney Port Regrets Turning Down One-Night Stand With Leonardo DiCaprio
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Of her rejecting the chance to hook up with the 44-year-old 'Titanic' actor, the 'Hills: New Beginnings' star says, 'I lost my chance and it's really one of my bigger regrets in life.'

AceShowbiz - Whitney Port may not be proud of one of her life decision, and it has something to do with actor Leonardo DiCaprio. "The Hills: New Beginnings" star revealed during her appearance on best friend Andrea Cuttler's "With Whit" podcast that she once missed the chance to spend the night with the "Once Upon a Time in Hollywood" actor.

"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 said during the episode earlier this week. She explained that she and Cuttler were at New York City's Avenue club back in 2009.

She went on sharing that she met the "Titanic" star there. "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," she recalled. "I feel like I was getting drunk at that point. I don't remember ... it's such a shame."

Port added that after exchanging phone numbers, she and DiCaprio kept in touch for some time as they were texting for six months before reuniting at the Roosevelt Hotel.

"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 continued, before adding, "If you didn't think I was cool, now you probably do. I wonder if he would remember that we had this relationship." Port, however, added that he "probably not."

Port is now married to producer Tim Rosenman following their 2015 nuptials. The pair welcomed son Sonny Sanford Rosenman in 2017. As for DiCaprio, the 44-year-old is dating her 22-year-old model girlfriend Camila Morrone.

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