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Whitney Port ‘regrets’ turning down ‘one-night stand’ with Leonardo DiCaprio

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Whitney Port ‘regrets’ turning down ‘one-night stand’ with Leonardo DiCaprio

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Leonardo DiCaprio is Whitney Port’s worst regret in life.

The Hills: New Beginnings star, 34, said on a recent edition of her With Whit podcast that she had rejected a “one-night stand” with the actor. Port and her closest friend Andrea Cuttler, who was there at the time of the alleged event, recorded the episode.

After chatting things up with Rihanna, she requested Andrea to recall the events leading up to her meeting Leo at a club.

‘I have been dying to tell people this story for ages,’ she said. ‘I feel like whenever I tell it to friends, no one believes me.’

‘Leo comes up to you and insinuates that he had missed the week before episode,’ Andrea, who said she was at the club where they first met, recalled.

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    ‘And you’re like, “is he telling me that he watches The City? This is very confusing, but also incredible.”

    ‘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 couldn’t leave.’

    ‘I feel like I was getting drunk at that point,’ Whitney said. ‘I don’t remember … it’s such a shame.’

    Whitney and Leo’s night out wasn’t the end of their connection, as she said the two had a ‘BBM relationship for like six months’ before reconnecting in LA.

    Whitney Port; Leonardo DiCaprio | CREDIT: JEAN BAPTISTE LACROIX/WIREIMAGE; BRIAN DOWLING/GETTY

    Later, the two exchanged phone numbers.

    After six months of messaging, Whitney stated that he wanted things to take a s*xual turn. “He invited me out to Teddy’s and he invited me back over to his house, and I said no,” Whitney explained. “I was too nervous. I had never had a one-night stand. I didn’t want to be with him alone.” In Whitney’s defense, she was 24 in 2009, which means she checked the 25 and under box on Leo’s policy, and could may get heated if she showed up at his apartment.

    ‘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.’

    She’s now married to the ‘love of her life,’ Tim Rosenman, and they have a two-year-old son named Sonny, so it must have worked out?

    Whitney also worried if Leo would remember anything about it in 2019. “I wonder if he would remember that we had this relationship,” she speculated.

     

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