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Everyone has that friend who always has shocking, hysterical, amazing stories to share over drinks. At least for today, Whitney Port is that friend.
On her podcast With Whit, the former Hills star shared a juicy-as-hell tale from more than a decade ago, when she turned down a one-night-stand with Leonardo DiCaprio.
“I have been dying to tell people this story for ages,” she said to friend Andrea Cuttler, who joined her on the episode.
“I feel like whenever I tell it to friends, no one believes me.”
The gist of the story is this: About 10 years ago, Port, then at the height of her fame on The City, went up to Rihanna in a nightclub to tell her they shared something in common: Port’s ex-brother-in-law was one of the writers on Rihanna’s hit SOS.
“And then Leo comes up to you to also,” Andrea, who was there on the night in question said, “and insinuated that, like, he had missed the week prior’s episode.
“And you’re like, is he telling me that he watches The City? This is very confusing, but also incredible.”
As Andrea remembered it “there was a phone number exchange” before they continued on to another nightclub with Leo and his entourage.
“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,” Andrea said.
“I feel like I was getting drunk at that point,” Whitney said, adding “I don’t remember … it’s such a shame.”
Port, now 34, said she and DiCaprio has a “BBM [BlackBerry Messenger] relationship for like six months” until they finally met up again in LA.
“He invited me out to Teddy’s [bar inside the Roosevelt Hotel] and he invited me back over to his house and I said no,” Port said.
Andrea joked that Whitney must have been the first women to refuse an invitation to Leonardo DiCaprio’s house, to which Port replied:
“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 admitted.
“If you didn’t think I was cool, now you probably do,” she laughed.
Still, it makes for one hell of a story.
