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Whitney Port Dishes on Relationship With Leonardo DiCaprio


Darn, had me fooled. Whitney (of The Hills and The City) why are you bringing this up again with new details? You had my hopes up that Leo had found someone age appropriate, but no. And that’s right – you’re married.

Whitney Port recently opened on her podcast, “With Whit,” about her seemingly innocent texting/bbm relationship with Leonardo DiCaprio from at least a decade ago. Girl, and you are still thinking about this? I think you let the mystique of Leo go to your head because didn’t you find someone better – you know, your husband. Whitney actually said, “It was one of her bigger regrets in life.” Hmm, living a sheltered life, are we? Maybe it was a light-hearted joke.

What are the deets on Leo?

Whitney goes on to talk about how they were friendly, communicating for around six months. She had one chance to go back to Leo’s and assumed it was leading to something. Could be. She chickened out because Leo is experienced and she didn’t hook up back then. But that might be why he was interested, Whitney. Just. Might. Be.

I wonder what they talked about during this six-months. And if it was leading to something more. She also recaps their first meeting saying, “I ran into Leonardo DiCaprio at a nightclub and we proceeded to exchange numbers.” She goes on, “We were at the nightclub and he had someone call me over. I immediately called my mom and stepped outside of the club. And then he was like, ‘Come over. We’re going to the one next door too. And I went with my best friend.’ “

When she accidentally dropped her phone in a puddle, it wouldn’t turn back on. She was worried “Leo’s gonna text me and I’m never gonna get it.” Her phone recovered and the rest is history.

What ended their texting rendezvous? She thinks it’s that their relationship was leaked. However, maybe he wasn’t that into you – we’ll never know unless Leo uncharacteristically speaks up. Whitney stated, “I wonder if he would remember that we had this relationship?” Uh, probably. Especially if he has a Google Alert on himself and this story pops up.

The Hills is over the hill (till another reboot). For more, listen to Dear Media’s With Whit: With Whitney Port podcast wherever you take in the talk.

TELL US – IS THIS STORY OLD NEWS? WOULD YOU HANG ONTO A RENDEVOUS WITH LEO? DO YOU THINK LEO WILL HEAR ABOUT HER PODCAST?



This story originally appeared on Realitytea

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