Whitney Port once had Leonardo DiCaprio‘s number, and for six months, the two exchanged texts in what can only be described as the most unexpected “situationship” of the 2000s. “I ran into Leonardo DiCaprio at a nightclub, and we proceeded to exchange numbers and had, like, a text relationship for six months…and that was fun,” Port revealed at a media event, according to JustJared. The Hills star and Hollywood’s ultimate leading man had a secret texting saga, devoid of cameras or staged drama—just messages back and forth between a reality star and an Oscar winner.
It all began when DiCaprio spotted Port at a club and had someone call her over. “I immediately called my mom and stepped outside the club,” she admitted. But disaster struck before the night ended: Port dropped her phone in a puddle, panicked over missing a text from Leonardo DiCaprio, and did what every early 2000s kid knew to do—stuck it in rice. Surprisingly, it worked, and the messages continued. However, just as quickly as this unexpected connection started, it ended, not because the spark faded.
Port confided in an executive producer about her texting connection with DiCaprio. “I told our executive producer about it because we were friends, and then I think he leaked it to the press, and then [DiCaprio] never texted me back,” she explained. One slip, and it was all over. For anyone who remembers The Hills, Port wasn’t the one caught up in dramatic love triangles or messy public breakups; she was the effortlessly cool girl who thrived while the rest of reality TV burned brightly around her. This made her story all the more intriguing.
DiCaprio, known for dating supermodels and maintaining a low profile in his personal life, clearly saw something in Port. Yet, Hollywood’s most elusive bachelor wasn’t prepared to let their low-key fling transform into tabloid fodder. Years later, this revelation feels like a peek into an alternate world rife with “what ifs.” What if Port had kept quiet? What if their texting thread led to something more significant? As she poignantly noted, “What could have been!”
This fascinating glimpse into their texting affair adds a fresh layer to the already captivating lives of Whitney Port and Leonardo DiCaprio, making fans speculate about the potential paths their interaction could have taken.
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