Whitney Port Regrets Turning Down A Night With The City Fan Leonardo DiCaprio

Photo: Michael Loccisano/Getty Images.
If The Hills: New Beginnings isn't enough nostalgia for you, then Whitney Port's podcast With Whit can supplement your early 2000s needs. Her most recent episode with Harper's Bazaar Entertainment Director Andrea Cuttler does not disappoint because not only does it involve her spinoff show The City, but it also features an almost-one-night-stand with Leonardo DiCaprio.
"I have been dying to tell people this story for ages," Port begins the anecdote, around 54 minutes into the episode. "I feel like whenever I tell it to friends, no one believes me."
It starts with Rihanna, like any good story should. Cuttler, who was there, says Port approached the singer at a nightclub, and the two gushed over each other's respective projects. Then, apparently, in walks Leo, insinuating that he, himself, is a fan of The City. The night progresses and while nothing happens between Port and DiCaprio, they do exchange numbers, and remained in contact via BBM (tbt) for around six months, according to the host.
However, the juiciest part of story takes place on a different night when they once again found themselves at the same event.
"He invited me back over to his house and I said 'no,'" Port said. "I was 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."
"If you didn't think I was cool, now you probably do!" she quipped. She's unsure if DiCaprio would even remember her, but if he does, someone let him know he missed his chance. Port happily married The City associate producer Tim Rosenman in November of 2015. They share a 2-year-old son named Sonny Sanford Rosenman.
DiCaprio, apparently, has started doing pottery with Brad Pitt, so I guess everyone got their own happy ending.

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