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. No cameras. There is no staged drama. Just messages back and forth between a reality star and an Oscar winner. It all started 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 before the night ended, disaster struck.
Port dropped her phone in a puddle, panicked over missing a text from Leo, and did what every early 2000s kid knew to do—stuck it in rice. It worked, and the messages continued.
But just as quickly as the unexpected connection started, it ended. And not because the spark faded. Port confided in an executive producer about the whole thing. “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 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 quietly thrived while the rest of reality TV was on fire. That’s what made this story even more intriguing.
DiCaprio, known for dating supermodels and keeping his personal life private, clearly saw something in Port. But Hollywood’s most elusive bachelor wasn’t about to let their low-key fling turn into tabloid fodder.
Years later, this throwback revelation feels like a glimpse into an alternate timeline. What if Port had kept quiet? What if that text thread had led to something more? But as she put it, “What could have been!”
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