Over the last several decades, an entirely new kind of celebrity has been born, the “reality” show star. Whether or not you buy that “reality” shows are as real as they pretend to be, the fact remains that the people who become famous from those series often aren’t known for any skill they possess. Instead, a lot of them have gained notoriety simply for their ability to seem entertaining when they are doing everyday things.
Since “reality” stars find themselves in the spotlight because of their everyday antics, it shouldn’t come as a surprise to anyone that they often aren’t taken as seriously as other stars. For example, it typically is only the top “reality” stars in the world that get invited to events that are attended by the most famous actors and musicians.
Given the fact that most “reality” stars tend to live in a completely different world than the top celebrities, it may surprise most people that Whitney Port interacted with a big star. In fact, according to something that Port said, she was propositioned by one of the biggest movie stars in the world and she rebuffed his advances. Unsurprisingly, she later came to regret that decision.
An Absolute Sensation
From 2004 until 2006, there was a pretty good chance that when people tuned in to MTV, Laguna Beach: The Real Orange County would be on no matter what time of day it was. A “reailty” show that focused on a group of high schoolers as they prepared for the next stage of their lives, the series introduced viewers to people like Lauren Conrad, Kristin Cavallari, and Stephen Colletti. Once Laguna Beach: The Real Orange County aired its final episode, MTV decided to give Conrad a spin-off series that would come to be known as The Hills.
Over the years, there have been a select few “reality” shows that have truly managed to become a sensation. Originally on the air from 2006 until 2010, at the height of The Hills’ popularity, it was one of the most talked-about shows in the world. As a result, there was a time in which it was nearly impossible to look at the covers of the tabloids without seeing one of the show’s main stars.
To this day, The Hills continues to have an avid fan base. In fact, the show remains popular enough that in 2019 MTV brought the series back when The Hills: New Beginnings debuted. While there are questions about how real that show actually is, the fact remains that the series has been successful enough that it is set to return for a third season as of the time of this writing.
An Unlikely Interaction
Of all the people who starred in The Hills, it could be argued that Whitney Port is the most boring. That certainly isn’t to say anything negative about Port as it simply is a reflection on the over-the-top antics of the show’s other stars.
Given that Port comes across as such a normal human being in comparison to her co-stars, it seemed very unlikely that she would be the one who was propositioned by a major movie star. Despite that, during a 2019 episode of Port’s podcast, With Whit, she revealed that she had the chance to share a night with Leonardo DiCaprio.
According to Whitney Port, she met Leonardo DiCaprio while they were both out for a night partying in Manhattan. Amazingly enough, Port says that DiCaprio implied that he watched The City, a The Hills spin-off that she starred in, and they traded numbers that night. After months of texting, DiCaprio “invited (Port) back over to his house and (she) said 'no'” according to Whitney.
At the time, Port had her reasons for rejecting the invite but that doesn’t mean she is happy with her decision now. "I was 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."
Incredible Company
Even though Whitney Port regrets turning Leonardo DiCaprio’s invite down, it makes sense that she was intimidated by the idea of being alone with him. After all, DiCaprio is the kind of movie star that only comes around once in a generation. Since DiCaprio is so famous, he likely hasn’t spent that much time thinking about the one date he missed out on. After all, DiCaprio has never gone too long without a romantic interest in his life.
Since Leonardo DiCaprio has dated so many women over the years, any attempt to list them all here would likely be foolhardy. That said, there certainly is room to touch on some of the most famous women DiCaprio has had on his shoulder. For example, DiCaprio has reportedly been linked to women like Naomi Campbell, Helena Christensen, Gisele Bündchen, Blake Lively, and Nina Agdal.