Whitney Port may be a fashion designer and currently starring on The Hills: New Beginnings but she’s also a happily married mom and wouldn’t have things any other way. Port, however, felt like now was the perfect time to drop a bombshell on her most recent podcast, With Whit: she turned a shot with Leonardo DiCaprio.
In hindsight, good on her, but back then? Damn. Whit prefaced by saying she’s been “dying to tell people this story for ages,” because she felt like whenever she’s told it to friends, no one believes her. Because, obviously. But her guest on the week’s podcast was her friend, Andrea Cuttler, who just happened to be her that infamous night—which meant she could back up Whitney’s story.
After much hype, Whit revealed Leo approached her at New York City’s Avenue club. At the time she was starring on The City and DiCaprio’s opening line involved something about missing the week’s prior episode, although it’s hard to imagine Leo being a die-hard MTV reality fan. Well, it worked and he and Whitney exchanged numbers and embarked on six months of BBM-ing (that’s what the elders called texting for Millennials and Gen Z-ers).
But then they met up again, about six months later. “He invited me out to [Hollywood Roosevelt Hotel’s exclusive bar] Teddy’s and he invited me back over to his house, and I said no,” recalled Port. “I was too nervous. I had never had a one-night stand. I didn’t want to be with him alone.” And Cuttler remembered the night, recalling that she was “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,” to which Port added she “was getting drunk at that point” and didn’t even remember what she and Leo talked about.
Sadly, that was the last time she heard from or saw him again, once a producer on The City leaked the story to the press.
Now, if given the opportunity, back then, again, would Whitney take it? Heck, yeah! “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 said. In 2009, Port would’ve been 24, and Leo, 34, which definitely would’ve put her in Leo’s target dating demographic. But if she was uncomfortable at the time, she clearly made the right choice and with a busy life, not to mention husband, Tim Rosenman, and son Sonny, she is doing just fine.
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Really trying to soak up all these moments. Yes, there’s been little sleep and bickering between Timmy and I because of the natural stress of traveling but I’m really trying to keep it all in perspective and soak in the fact that Sonny will never be this age again and that we really are in one of the most beautiful places in the world. I don’t want to leave but also am so excited to get back to my grind next week as well! STAY PRESENT WHITNEY! And to all of you too. ❤️