The Hills: New Beginnings: Whitney Port Recalls The Time She Turned Down A One Night Stand With Leonardo DiCaprio

The Hills: New Beginnings star Whitney Port is happily married to Tim Rosenman. They are even the proud parents to an adorable little boy, Sonny but life could have been different for the reality TV star.

On the most recent episode of her podcast With Whit, Port recalled how her romantic life might have been if she had accepted an invitation to Leonardo DiCaprio’s house. She and her best friend, Andrea Cuttler discussed the night Port almost had with the Hollywood A-list star.

In 2009 the MTV star and Cuttler were at New York City’s Avenue club because Port was filming The City. The best friends had just met Rihanna and didn’t think the night could get any better.

Cuttler and Port were in for the surprise of their lives when DiCaprio introduced himself. The Hills alum explained she chatted with the Hollywood hunk, then they exchanged phone numbers.

Port and DiCaprio texted for about six months but only met up once during that time. The reason she never really hooked up or fell for the movie star was because of her nerves.

“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. If you didn’t think I was cool, now you probably do. I wonder if he would remember that we had this relationship,” Port expressed.

The two besties then went on to speculate about what life might have been like if Port has said yes that night. If her nerves didn’t get the best of her, would she and DiCaprio have sparked a romance?

No one will ever know what might have been between Whitney Port and Leonardo DiCaprio since she turned him an invitation to his house. Even though The Hills: New Beginnings star says it is one of her biggest life regrets, she is unbelievably happy with how her life turned out.

Still though sometimes it is fun to wonder what might have been, especially when it comes to a romance with a Hollywood hunk like DiCaprio. Plus, now Port is finally comfortable telling how she turned down the Once Upon A Time In Hollywood actor’s one-night stand invitation.