"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 excitedly said, before explaining that in 2009, she and Cuttler were at New York City's Avenue club when -- after meeting Rihanna -- DiCaprio came up to her and they exchanged phone numbers.
Port then said that she and DiCaprio texted for six months, only reuniting once during that time.
"He invited me out to Teddy's and he invited me back over to his house, and I said no," she revealed. "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," she added. "If you didn't think I was cool, now you probably do."
"I wonder if he would remember that we had this relationship," Port said.