For a relatable reason.


For Whitney Port, the one that got away isn't just anyone, it was Leonardo DiCaprio. According to Entertainment Tonight, in the latest episode of Port's podcast, With Whit, the reality TV stalwart explained that she once had the chance to hook up with DiCaprio, but was "too nervous" to actually go through with it. She explained to her co-host, her friend Andrea Cuttler, that it's her biggest regret in life.

"I have been dying to tell people this story for ages! I feel like whenever I tell it to friends, no one believes me," Port said. She added that after she and DiCaprio initially met at New York City's Avenue club, they texted for over six months and only met each other one other time: "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. I didn't want to be with him alone."

Whitney Port Premiere Of MTV's "The Hills: New Beginnings" - Arrivals
Credit: Michael Tran/Getty Images

In 2009, DiCaprio already had plenty of high-profile relationships. He and Gisele Bundchen, perhaps his most high-profile relationship, had fizzled out and he was in an on-again, off-again relationship with model Bar Refaeli in Port's timeline of events.

"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 added. "If you didn't think I was cool, now you probably do."

Port went on to say that she thinks DiCaprio probably doesn't remember their six-month text exchange or the fact that he asked her over. Port's never even been mentioned in roundups of DiCaprio's long list of girlfriends. It may be for the best, though. Port married Tim Rosenman in 2015 and the couple shares a 2-year-old son, Sonny. She's riding high on the revival of her star turn on The Hills with The Hills: New Beginnings, so she's probably not sweating anything that didn't happen with Leo.