On her With Whit podcast this week, the star of "The Hills" and "The City" and her longtime friend Andrea Cuttler shared stories from their clubbing heydays and claimed Port once turned down an invitation to Leo's home.
After talking about their wild nights back in the day, Port asked if there was anything else her guest wanted to talk about. "Do you wanna tell the Leo story?" asked Andrea. Calling it "one crazy night in New York," Port said she's been "dying to tell people this story for ages," noting that none of her friends believe her when she tells them.
"Can you just validate the story please," she asked Cuttler, who was there to watch it all go down and explained exactly what happened.
"So we went to Avenue and this was late aughts, 2009. We go to the club, Rihanna is there," recalled Cuttler. "Rihanna is there at the front table, you go to her to tell her that your ex brother in law wrote the song 'SOS.' And then she tells you that she loves 'The Hills' and you're like, 'What? Rihanna watches the 'The Hills' and 'The City?'"
But RiRi wasn't the only one.
"Then who comes up to [Whitney] to also tell you, but Leonardo DiCaprio," she continued. "Leo comes up to you, insinuated that, like, he had missed the week prior's episode. And you're like, your head is spinning, is he telling me that he watches 'The City'? This is very confusing, but also incredible."
Looking back, Port was able to recall exactly what she had on that night as she flirted with the now-Oscar-winner. "I was wearing a little black t-shirt, baby tee with high waisted black floral shorts and high high heels," she said. "It was all legs!"
"There was a phone number exchanged, then we went to 1OAK around the corner because he was going with his friends and asked if we would meet him, which like, yes," Cuttler continued. "I remember dancing alone on the dance floor because you were in a corner talking to him and I didn't want to intrude, but also like couldn't leave."
Port, unfortunately, doesn't remember what the two talked about, explaining, "I feel like I was getting drunk at that point ... it's such a shame."
The two then began messaging each other on their BlackBerry phones until 6:00 in the morning. "Then we had a BBM relationship for like six months," Port said. She only saw him in person one more time after that, after he invited her to a night out at Teddy's at the Roosevelt in Hollywood.
"He invited me out to Teddy's and he invited me back over to his house, and I said no. I was too nervous. I had never had a one-night stand," she said. "I didn't want to be with him alone. I didn't know what it had to be. If Leonardo DiCaprio invites to you to his house ... 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."
Whitney said that her turning him down isn't what "stopped the relationship," however. According to Whitney, she told a producer for "The Hills" what happened, he leaked it to Perez Hilton and Perez put up a post about it on his site.
"Then he never spoke to me again," said Whitney. "I wonder if he would even remember we had this relationship, if I said hi to him, he'd say hi back. I could have been married to Leonardo DiCaprio."
Port has been happily married to Tim Rosenman since 2015 and they share one son, Sonny. Leo's not doing too bad himself, having dated a number of younger models in the years since 2009, including current, 22-year-old girlfriend Camila Morrone.