Plot twist! Whitney Port reflected on a major regret she has in life: turning down a fling with Leonardo DiCaprio.
“He invited me out to Teddy’s and he invited me back over to his house, and I said no,” Port, 34, revealed on her “With Whit” podcast on Tuesday, August 13. “I was too nervous. I had never had a one-night stand. I didn’t want to be with him alone.”
In the episode, Port continued to tell her guest, longtime pal Andrea Cuttler: “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!”
As Port recalled her former experience with the 44-year-old, she asked Cuttler to “validate” the story since she was present for the 2009 encounter. The MTV star also noted that “whenever I tell it to friends, no one believes me.”
Port revealed that the Academy Award winner approached her at New York City’s Avenue club, which occurred while she was starring on The City. Cuttler then claimed that DiCaprio “insinuated that, like, he had missed the week priors episode.” Thereafter, Port’s pal noted that “a phone number exchange” commenced and the ladies headed with DiCaprio to another club.
“I remember 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,” Cuttler recalled, to which Port added that she believed she “was getting drunk at that point” but she did not “remember” what she’d discussed with the environmentalist.
Port then claimed that she maintained a BBM — BlackBerry Messenger — “relationship” with DiCaprio for roughly six months after their night out. However, the last time she saw the Aviator star was when he invited her to Teddy’s and asked her to leave with him. The duo never spoke again after a producer on The City leaked the story to the press.
In October 2009, a source told Us Weekly that Port and DiCaprio had never hooked up. “It’s about as true as The City — it’s made up! They don’t know each other. They never exchanged numbers,” the insider said at the time.
Though Port never got with DiCaprio, she married producer Tim Rosenman in 2015. The coupled welcomed their son, Sonny, in 2017.
DiCaprio, meanwhile, is dating model Camila Morrone.
