Whitney Port of The Hills has revealed that she once turned down the offer of a “one-night stand” with Leonardo DiCaprio, calling the situation one of her biggest “regrets” in her life.

Honestly, the way I see it, having a chance to bone Leo and turning it down is actually way cooler and a way better story than if you went through with it, but I respect Whitney’s point of view all the same.

The story came out during a recent episode of her podcast Whit WhitHer friend Andrea Cuttler, who was present during the Leo incident, was on the show as a guest to back her up.

“I have been dying to tell people this story for ages!” the host said. “I feel like whenever I tell it to friends, no one believes me.”

Allegedly, the pair met on a night out in New York way back in 2009 – they traded phone numbers and then talked in the corner of the room for “most of” the evening.

They texted on BlackBerry Messenger – which is maybe honestly my favourite part of the story – for the next six months, but it was sadly not to be.

Whitney Port went on to say:

“I saw him one more time. I saw him at the Roosevelt Hotel. 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. … 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. He never spoke to me again.”

Leo and his reps have not commented on any alleged flirtation between him and the reality star.

Image: Getty Images / Michael Tran / Franco Origlia