Whitney Port's Biggest Regret Is Not Sleeping With Leonardo Dicaprio

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Did Whitney Port Date Leonardo DiCaprio? New Details On Rumors She Turned Him Down

We all have dating regrets. Perhaps we wonder what would have happened if we told our crush we were into him? Or maybe we stayed too long with one guy and regret that. Even Whitney Port has some dating regrets. In her case, she regrets not going home with Leonardo DiCaprio that one time he invited her over. Wait, what? Did Whitney Port date Leonardo DiCaprio?

1. It all started back in 2009

Whitney Port was talking about one of the "bigger regrets in life" on her With Whit podcast this week. The 34-year-old The Hills: New Beginnings star said that she was out at Avenue, a popular Manhattan club at the time, with her BFF Andrea Cuttler one night in 2009. Cuttler appeared on the podcast with Whitney. Port said: "I have been dying to tell people this story for ages! I feel like whenever I tell it to friends, no one believes me." Whitney and Andrea met Leonardo DiCaprio during a night out. Whitney and Leo exchanged phone numbers and spent much of the evening in a corner talking to one another. Port said that she and Leo texted on BlackBerry Messenger (OMG remember BBM-ing?!) for six months until she saw him again.

2. Leo was a fan

When Whitney and Leo met up that night in New York City, he reportedly told her that he watched Whitney's reality show The City. That show was a Hills spin-off that followed Port from Los Angeles to New York City where she went to work for Diane Von Furstenburg and emabrked on her own career as a fashion designer.

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3. They met up in L.A.

About six months later she saw DiCaprio in L.A. at the Roosevelt Hotel. He invited her out to a bar and then back to his house. She 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.” Port and DiCaprio never spoke again.

4. Who was Leo dating back then?

Leonardo DiCaprio is a famous modelizer. Back in the 2009 era he was in a long-term, on-off relationship with model Bar Refaeli. The couple dated from 2005 to 2011 wirth a six-month break in 2009, which is presumably when DiCaprio was attempting to seduce Whitney Port.  

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5. It all worked out

In the end, it all worked out for Whitney. She ended up marrying Tim Rosenman, one of the producers of The City, in 2015. Their son, Sonny Sanford Roesenman, was born in 2017. 

6. What's Whitney up to today?

Well, besides appearing on the reboot of The Hills  called The Hills: New Beginnings and being a wife and mom, she's actively involved in her new podcast, With Whit. In fact, the episode about her near-liason with Leonardo DiCaprio is the 14th episode of her podcast. 

Amy Lamare is a Los Angeles based freelance writer covering entertainment, pop culture, beauty, fashion, fitness, technology, and the intersection of technology, business, and philanthropy. You can find her on Instagram and Facebook.