Shaun White Dating History

Let’s be honest: when you think of Shaun White, you probably picture a blur of red hair and a snowboard soaring over a halfpipe, defying gravity as if he personally told physics to take the day off. But off the slopes, the man they call the Flying Tomato has had a love life almost as dizzying as his signature frontside double cork. It’s a history of high-profile romances, awkward public breakups, and enough broken hearts to fill an Olympic-sized swimming pool.

The saga officially kicked off in the mid-2000s when White was dating Lindsay Vonn. Yes, the queen of alpine skiing herself. For a while, they were the ultimate winter sports power couple, the kind of pair that made your grandparents say, “My, they make such lovely athletic babies.” The internet collectively swooned. But all that snow and gold medal pressure eventually melted into a quiet breakup around 2007, leaving fans to wonder if they’d hugged too aggressively after a race.

Enter the Pop Star Era

Then came Ashlee Simpson. In 2007, Shaun reportedly dated the pop singer, a pairing that made about as much sense as a snowboarder in a desert, but somehow worked for a hot minute. They were spotted holding hands at a Lakers game, looking like a magazine cover that someone photoshopped together. The relationship fizzled faster than a snow cone in July, but it set a pattern: Shaun liked his partners famous, and with their own brand of chaos.

After Ashlee, there was a brief, mysterious fling with Sarah Barthel of the electro-pop band Phantogram. This was Shaun’s “indie era,” where he probably wore a beanie indoors and pretended to understand obscure synth remixes. It was low-key, lasted a few months, and remains so undocumented that fans still joke about it being a conspiracy theory. Did it happen? Possibly. Did anyone care? Not really, because soon, he’d find his supernova.

The Main Event: Brennan Mejia

Brennan Mejia—a model, actress, and all-around radiant human—entered Shaun’s life in 2014, and suddenly the gossip columns went thermonuclear. They were everywhere: red carpets, Hawaiian beaches, and Instagram posts so sugary they threatened to give dentists job security. They were engaged in 2019, with a ring so big it could double as a snowboard binding. The internet planned their wedding catering. People cried.

But here’s the surprising twist: in 2020, right before the Tokyo Olympics (which, for Shaun, was the summer Olympics, so, culture shock), they quietly called off the engagement. Reports say it was amicable, and Shaun later admitted he “wasn’t ready” for marriage. Translation: The Flying Tomato was scared of commitment. We’ve all been there, except we weren’t risking a multi-million dollar brand.

And then—hold your hot cocoa—in early 2023, Shaun started dating Nina Dobrev. You know, the Vampire Diaries star who’s also played cupid for half of Hollywood. They were photographed skiing together (obviously), and the Internet basically let out a collective scream. They looked cute, happy, and for a moment, it seemed like Shaun had finally traded his snowboard for a stable relationship. But in late 2023, reports surfaced that they’d parted ways, the breakup blamed on “busy schedules.” Because, of course, a vampire slayer and a snowboard god don’t exactly have overlapping appointment books.

The Surprising Ex Files: Not Just Models

Before you think Shaun only dates celebrities, let’s not forget Camille Kostek, the Sports Illustrated model who famously didn’t date him, but was rumored to have a “very close friendship” with him in 2020. The rumor mill was so aggressive that her publicist had to issue a statement, which is basically the celebrity equivalent of yelling “WE’RE JUST FRIENDS!” through a megaphone. Also, there was a very brief connection with Kendall Jenner in 2016, a rumor so hot it lasted about three news cycles before everyone realized Kendall was too busy being a Kardashian to ski.

One hilarious detail: almost every ex has mentioned Shaun’s obsessive work ethic. Multiple sources say he’d cancel dinner plans to practice halfpipe tricks at midnight. So, if you ever date an Olympic athlete, expect to be second place to a snowboard. It’s not personal; it’s physics.

The Weirdest Twist of All

In 2024, Shaun confirmed he was dating the actress Lili Reinhart—from Riverdale. Yes, because why date a normal person when you can date someone who has faced a fictional murderous gargoyle king? They were spotted holding hands in Los Angeles, looking suspiciously like a couple who still haven’t watched each other’s movies. The relationship is reportedly very low-key, which, for Shaun, is the equivalent of a quiet retirement. He even said in an interview that he’s “finally learning to relax.” We’ll believe it when we see him skip a snowboard session for brunch.

So, what have we learned from Shaun White’s dating history? Three things: He has a type (blonde, famous, athletic, or a mix of all three). He breaks up with people faster than he lands a 1440. And most importantly, his love life is still more entertaining than half the shows on Netflix. Who needs a drama series when you have the Flying Tomato sliding through Hollywood like a rogue snowball?

In the end, whether he ends up with Lili or someone new, one thing is certain: Shaun White’s heart will always be a halfpipe. It’s cold, it’s steep, and you’re probably going to wipe out spectacularly trying to navigate it. So, pass the popcorn. This story isn’t over.