'I was way too nervous to do it, and then I lost my chance.'
The Hills: New Beginnings star Whitney Port opened up on her podcast With Whit about a chance Leonardo DiCaprio encounter (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 was not meant to be, and she rejected him, which she called “one of the bigger regrets of my life”.
Recounting the story to her close friend, Harper’s Bazaar entertainment director Andrea Cuttler, she revealed that the meeting took place in 2009 at a club called Avenue in New York City. At the time, Port was still starring on The Hills spin-off called The City and DiCaprio was described by Cuttler as being “peak Leo”.
Cuttler recounted the story, saying, “We go to the club. Rihanna’s there at the front table, you [Port] go up to her to tell her that your ex brother-in-law wrote the song S.O.S which was like her big hit. This was like before she was a thing.”
Clearly, Port’s reality TV shows were a favourite with the A-list crowd, as Cuttler revealed, “[Rihanna] tells you that she loves The Hills and you’re like, ‘What? Rihanna watches The Hills and The City?’ And all this s**t and it’s so crazy. But who comes up to her to also tell you, but Leonardo DiCaprio.”
Cuttler and Port later revealed that DiCaprio “insinuated that he had missed the week prior’s episode [of The City]”, and called the fact that DiCaprio was a secret The City stan “incredible”. Following the conversation, DiCaprio and Cuttler exchanged numbers and were then invited to a second location at 1 OAK to meet with DiCaprio and the rest of his friends.
Although Cuttler said that the pair spent most of the night sitting in a corner and talking, Port added that she was “probably drunk” at that point and couldn’t remember what they had talked about. After that, Port revealed that she and Leonardo DiCaprio embarked on a six month “BBM relationship”; a reference to the Blackberry messaging system which was popular at the time.
Port said that she ended up seeing DiCaprio one more time and said, “He invited me back over to his house and I said no!”
Explaining that she was “too nervous”, she continued, “I had never had a one night stand and I didn’t want to be with him alone. I was way too nervous to do it, and then I lost my chance. It’s really one of my bigger regrets in life.”
While Port may have turned him down, she explained that their relationship didn’t come to an end then. It all fell apart when she told an unnamed producer on The Hills that she and DiCaprio were talking to one another, who then leaked the news to celebrity gossip site PerezHilton.
The article alleged that DiCaprio had been “paying for her flights back and forth between coasts for visits” adding, “What could Leo possibly see in this girl? She has no personality, no real claim to fame, and if we maybe frank for just a minute, looks like an elongated dwarf!”
After the story broke, DiCaprio and Port’s text relationship came to an end.
Port said, “And then he never talked to me again.”
DiCaprio with Camila Morrone / SplashNews.comWhile things may not have worked out for DiCaprio and Port, they both seem to have happily moved on. 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 Cannes Film Festival.
That hasn’t stopped Port from imagining what might have been. She asked, “I wonder what [DiCaprio] would even - like [would he] remember that we had this relationship? If i said hi to him, if he would say hi back?”