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Believe it or not, before the world was obsessed with every frame of Dune or the latest paparazzi shots from a Kardashian-adjacent garden party, Timothée Chalamet was just another kid in a drama elective. Well, mostly another kid. He was at Fiorello H. LaGuardia High School—the "Fame" school—in Manhattan. And his first big romance? That would be with Lourdes Leon, the daughter of, you know, Madonna.
It’s one of those Hollywood "what if" stories that actually happened. In 2013, long before the internet crowned him its collective boyfriend, Timothée Chalamet and Lourdes Leon were a genuine high school item. They weren't just two famous names thrown together for a PR stunt; they were teenagers navigating the halls of an elite performing arts school while their careers were just beginning to simmer.
Honestly, looking back at it now feels like a fever dream. Imagine being in 11th grade and seeing the guy from Homeland holding hands with Madonna’s eldest daughter by the lockers.
The LaGuardia Days: Where It All Started
They met as students. At the time, Timothée was making a name for himself as Finn Walden on the Showtime series Homeland. Lourdes—or "Lola" to her inner circle—was already a fashion force, having co-created the Material Girl clothing line with her mom.
They weren't just dating; they were artistic collaborators. They both appeared in a school production of Sweet Charity. You can actually find old photos of them on stage together if you dig deep enough into the archives of NYC high school drama departments.
What was the vibe?
It was very "New York cool." They were spotted walking hand-in-hand in the East Village, looking like every other stylish teen in the city, except for the occasional bodyguard or trailing photographer. A source told Page Six back in 2013 that it was "common knowledge" at the school that they were dating. It wasn't some dark secret, just a part of the school's social fabric.
Timothée Chalamet and Lourdes Leon: That Infamous Date with Madonna
One of the best stories from this era came out years later during a SiriusXM interview with Andy Cohen. Andy, being Andy, didn’t hold back. He asked Timothée about the time he met Lola’s mom.
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Timothée turned bright red. You could tell he was trying to be respectful but also totally embarrassed by the memory. He recalled a night out where he was dancing with Lourdes, his buddy Joey, and Madonna.
"I usually don't talk about this stuff," he told Cohen, laughing. He described it as a "really fun night" where the Queen of Pop herself was just out on the dance floor with them. It’s a wild mental image—a teenage Timmy trying to keep his cool while the world’s biggest pop star is doing the Macarena (or whatever the 2013 equivalent was) right next to him.
The 2021 Confirmation
For years, the relationship was mostly a rumor or a "people say" kind of thing. Neither of them really confirmed it while it was happening. Then came April 2021.
Lourdes sat down for a rare, candid interview with Vanity Fair. She didn't hold back.
"I respect him a lot, we were a little item," she said. "My first boyfriend."
That quote basically broke the internet for a few days. It was the first time either of them had used the word "boyfriend." She spoke about him with such genuine warmth. It wasn’t messy. It wasn’t bitter. It was just a sweet reflection on a first love.
Why did they break up?
The details are murky, but the consensus is that they were just... kids. They dated for about a year. By 2014, reports suggested they had gone their separate ways. Chalamet was graduating and heading off to college (briefly at Columbia, then NYU), and Leon was finishing up her own studies before heading to the University of Michigan.
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Distance and the transition to adulthood do a number on most high school relationships. Being "Madonna's daughter" and "the next big thing in Hollywood" probably didn't make it any easier.
Are They Still Friends?
Short answer: Yeah, seemingly.
In that same 2017 interview with Andy Cohen, Timothée mentioned that he’d spoken to Lourdes about his role in Call Me By Your Name. She hadn't seen it yet at the time, but he said she was "excited to" and kept "teasing" him about all the public appearance stuff he had to do for the Oscar campaign.
It’s refreshing, really. In a world where every celebrity breakup turns into a three-part Netflix documentary or a "diss track," these two seem to have mastered the art of the mature "ex-files."
Why the Internet is Still Obsessed
People love a full-circle moment. When Timothée started dating Lily-Rose Depp, fans pointed out that he clearly has a thing for "cool, artistic daughters of icons" (Lily-Rose being the daughter of Vanessa Paradis and Johnny Depp).
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Then came the Kylie Jenner era, which feels like a total departure from the "LaGuardia artsy kid" vibe. Whenever things get rocky in his current relationship—as tabloids like the National Enquirer loved to claim in late 2025—the name "Lourdes Leon" inevitably pops back up.
There's this romanticized idea that your first love is your "true" love. Fans love to speculate that Timothée might one day find his way back to the girl who knew him before he was Paul Atreides.
The Actionable Takeaway for Fans
If you're following the Timothée Chalamet and Lourdes Leon saga, here’s how to stay updated without falling for the fake tabloid "reconciliation" bait:
- Watch the Interviews: The Vanity Fair (2021) and Radio Andy (2017) interviews are the only times they’ve actually spoken about each other. Anything else is usually "sources say."
- Follow the Career Trajectories: Lourdes is carving out a massive niche in the high-fashion world (think Mugler and Marc Jacobs). Timothée is the king of the box office. They move in the same circles, so a "reunion" photo at a Met Gala or a fashion week party is always a possibility.
- Respect the Privacy: Both stars have been vocal about hating the "paparazzi culture." They’ve managed to keep their current friendship (or lack thereof) mostly off the grid, which is probably why it has lasted this long.
The story of Timmy and Lola is a reminder that even the biggest stars had a "first boyfriend" or "first girlfriend" who remembers them when they were just trying to pass a dance class and avoid being embarrassed by their parents.
Even if that parent happens to be Madonna.
Next Steps:
If you want to see more of their history, you should check out the archival footage of LaGuardia High School's 2013 productions. It's the best way to see their chemistry before the Hollywood machine took over. You can also look into Lourdes' recent fashion campaigns to see how she’s built a brand entirely separate from her "first boyfriend" or her famous mother.