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If you remember that Whitney Port—former Teen Vogue intern, star of The Hills and the girl that went to Paris—once dated Leonardo DiCaprio—Academy award-winner who’s reportedly never dated a girl over 25—for a brief six months in the 2000s then you may be eligible for compensation. Or a lifetime supply of retinol. Or even a free drink from the now-defunct Los Angeles beau monde haunt Les Deux.
Indeed, instead of letting this fever dream moment in pop culture fade to oblivion, the former reality TV fixture turned podcast host decided to dredge this core memory from the depths of our hippocampus by finally revealing the whole truth about their short-lived romantic rendezvous.
“I ran into Leonardo DiCaprio at a nightclub and we proceeded to exchange numbers and had like a text relationship for 6 months,” Port shared at a summit hosted in Los Angeles.
Of course, for Gen-Z readers, this type of cute-meet is the dream scenario most millennials would wish for when it came to meeting their partners. A typical Saturday night would see us sport an LC-approved headband and slurping down vodka cranberries until it was time to add our crush’s name to our Blackberry’s address book. But as we now recall, Port’s own star-studded version of events is fulfilling the Y2K fantasy we forgot we had.
The With Whit host didn’t disclose the name of the club, but did explain their fêted relationship almost didn’t get off the ground. “I ended up that night dropping my cell phone in a puddle of water, and it wouldn’t turn on and I was freaking out because I was like ‘Leo’s gonna text me and I’m never gonna get it’. And then I stuck it in rice and it worked.”
Sadly, Port ended up getting ghosted by DiCaprio after an executive producer of The Hills linked their virtual romance to the press. Given that Port would’ve turned 25 in 2010, we’re assuming this interaction took place well before then.
And while nothing ever eventuated from their fling, it’s an entertaining reminder of just how lawless the 2000s actually were. Scarlett Johansson and Ryan Reynold’s secret wedding, anyone?
