“I was way too nervous to do it, then I lost my chance.”
The Hills: New Beginnings star Whitney Port has opened up on her With Whit podcast about a chance encounter with Leonardo DiCaprio (guest starring Rihanna), which led to six months of texting and the opportunity to have a “one-night stand” with the Titanic actor. However, Port revealed that it wasn’t meant to be, and she dismissed it, which she called “one of the biggest regrets of my life.”
Telling the story to her close friend, Andrea Cuttler, director of entertainment at Harper’s Bazaar, she revealed the encounter took place in 2009 at a club called Avenue in New York City. At the time, Port was still starring in The Hills spin-off called The City and DiCaprio was described by Cuttler as “peak Leo”.
Cuttler told the story, saying, “We’re going to the club. Rihanna is there at the head table, you [Port] go to her to tell her that your ex-brother-in-law wrote the song SOS which was like his big hit. It was like before she was a thing.
Clearly, Port’s reality TV shows were favorites of the A-list crowd, as Cuttler revealed, “[Rihanna] tells you she loves The Hills and you’re like, ‘What? Rihanna watching The Hills and The City?’ And all that shit and it’s so crazy. But who comes up to her to tell you that too, but Leonardo DiCaprio.”
Cuttler and Port later revealed that DiCaprio “implied he missed last week’s episode. [of The City]”, and called the fact that DiCaprio was a secret The City stan “incredible”. After the conversation, DiCaprio and Cuttler exchanged numbers and were later invited to a second location at 1 OAK to meet DiCaprio and the rest of his friends.
Although Cuttler said the couple spent most of the night sitting in the corner and talking, Port added that she was ‘probably drunk’ at the time and couldn’t remember what they had spoken. After that, Port revealed that she and Leonardo DiCaprio had started a six-month “BBM relationship”; a reference to the Blackberry messaging system that was popular at the time.
Port said she ended up seeing DiCaprio one more time and said, “He invited me to his house and I said no!”
Explaining that she was ‘too nervous’, she continued: ‘I had never had a one night stand and didn’t want to be alone with him. I was way too nervous to do it, then I lost my chance. This is truly one of my biggest regrets in life.
Although Port may have turned it down, she explained that their relationship didn’t end there. It all came crashing down when she told an anonymous producer on The Hills that she and DiCaprio were talking, who then leaked the news to celebrity gossip site PerezHilton.
The article alleged that DiCaprio had “paid for his round-trip flights between the coasts for sightseeing,” adding, “What could Leo see in this girl? She has no personality, no real claim to fame, and if we can be frank for a minute, she looks like a lying dwarf!
After the story broke, DiCaprio and Port’s textual relationship ended.
Port said, “And then he never spoke to me again.”
While things may not have worked out for DiCaprio and Port, they both seem to have moved on happily. Port has been married to Tim Rosenman since 2015 and has a son called Sonny Sanford Rosenman, while DiCaprio and model/actress Camila Morrone have been seen together at events including Coachella and the Cannes Film Festival.
That didn’t stop Port from imagining what might have been. She asked: “I wonder what [DiCaprio] would even like [would he] remember we had this relationship? If I said hello to him, would he say it back to me? »
Whitney Port’s With Whit podcast can be heard on Apple Podcasts and Spotify.