Whitney Port first came to prominence back in 2006 when she appeared on the hit MTV reality series, The Hills. While Port played a supporting role to that of Lauren Conrad, she became a household name and earned her own spin-off three years later, called The City.
In addition to becoming a TV show lead, Whitney has also made a name for herself in the world of fashion and women's empowerment. It goes without saying that Port has achieved so much, which fans have been able to witness as Whitney documents her life on her YouTube channel.
While she's doing incredibly well today, there was no moment like 2008 where the ladies of The Hills were at their prime, so much so that Whitney caught the attention of a mega Hollywood A-lister. After texting all night and being invited back to his room, Port politely declined but kept in touch regardless. Who did Whitney nearly have a juicy rendez-vous with? Let's find out!
Which A-List Star Did Whitney Almost Date?
Whitney Port has certainly done it all! From appearing on her own reality TV show, designing her own fashion line, motherhood, all the way to flirting with Hollywood's most eligible bachelor.
Although Port has had a number of crazy experiences, such as jet-setting to Paris alongside Lauren Conrad or falling on live television during her Good Morning America segment back in 2007, which ended up airing on The Hills, it was none other than her brief romance with Leonardo DiCaprio, or lack thereof, that remains her biggest moment!
While this was a huge moment, it is also Whitney's biggest regret, ever! The star revealed that back in 2009, she met Leonardo DiCaprio during a night out partying in Manhattan, New York. Port revealed that the two had exchanged numbers and had Leo approach her a number of times claiming that he was a huge fan of her show, The City.
Although fans would have never guessed Leo watched MTV, it seems as if he has had his eyes set on Whitney Port for quite some time. Things quickly went from crazy to crazier after she was invited back to Leo's place. While this is just about anyone's dream come true, the designer let fans know that she isn't a "one night stand" kind of girl.
Port went on to describe the weeks following their night out, saying that they continued to text for quite some time, and while she may not have felt comfortable at the time, Whitney today would have totally went for it, which is why she claims the tale as one of her "biggest regrets in life", and we certainly do not blame her!
Luckily for Whit, she has since found love with none other than hubby, Tim Rosenman, with whom she shares their three-year-old son, Sonny.