The internet absolutely lost its mind for a second there. If you were on TikTok or X in the summer of 2024, you probably saw the grainy paparazzi shots: Tobey Maguire, the guy who literally defined a generation’s Spider-Man, with his arm draped around a young woman in a white dress. That woman was Lily Chee.
The setting was Michael Rubin’s annual White Party in the Hamptons. It’s basically the Super Bowl of celebrity social climbing—everyone from Drake to Kim Kardashian is there, all wearing head-to-toe white and pretending they aren't sweating through their linens. But it wasn't the star-studded guest list that caught people's attention. It was the fact that Tobey is in his late 40s and Lily was 20 at the time.
The Photo That Sparked a Million Tweets
Let's look at the facts. Tobey Maguire was 49 years old during that Independence Day weekend. Lily Chee was 20. For those doing the math at home, that's a 29-year age gap.
Social media users didn't hold back. People pointed out that Lily wasn't even born when the first Spider-Man movie hit theaters in 2002. Others started comparing him to his long-time friend Leonardo DiCaprio, who has a well-documented "age limit" for his dating life. Honestly, the memes were pretty brutal.
But here is the thing: a single photo of a guy with his arm around someone doesn't always equal a "serious relationship." Sometimes, it's just a guy being a guy at a party. Or, if you believe Tobey’s ex-wife, it was something else entirely.
Jennifer Meyer Enters the Chat
In a move you don't see often in Hollywood, Tobey’s ex-wife, jewelry designer Jennifer Meyer, actually stepped in to defend him. She didn't just ignore the noise. She went straight to the comments section on Instagram.
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When a user left a pretty nasty comment on her page asking why her ex-husband was "banging" someone only three years older than their daughter, Ruby, Meyer didn't hold back. She claimed that Tobey was simply "kindly helping a friend to her car." She called the rumors "nonsense" and insisted he was just being a "good guy."
It’s worth noting that Tobey and Jennifer have one of the friendliest "ex" relationships in the industry. They split in 2016 and filed for divorce in 2020, but they are constantly seen together at their kids' events. Just recently, they were spotted together celebrating their daughter Ruby’s high school graduation. So, when Jennifer says something about Tobey’s character, people usually listen.
Who is Lily Chee Exactly?
If you aren't a Gen Z influencer aficionado, you might have been wondering who the girl in the white dress actually was. Lily Chee isn't just a "random model." She’s been in the industry since she was nine years old.
She was famously "discovered" by an agent while she was grocery shopping in a local store. Talk about a lucky break. Since then, she’s built a massive following:
- Over 1.6 million followers on Instagram.
- A successful YouTube channel with hundreds of thousands of subscribers.
- Acting credits like playing Young Elektra in Marvel’s Daredevil series on Netflix.
- Modeling gigs for heavy hitters like Dior, Valentino, and Ralph Lauren.
She’s also a regular in the high-society party circuit. At the Michael Rubin party, she was actually there with a group of friends, including Rubin’s own daughter, Kylie. This adds a bit of weight to the "family friend" argument. If she's best friends with the host's daughter, it makes sense why she'd be in the same orbit as a veteran star like Tobey.
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The "Wolf Pack" Reputation
We can't talk about Tobey Maguire without mentioning his history. Back in the 90s, he was a core member of what the press called the "Pussy Posse" (later rebranded to the more PR-friendly "Wolf Pack"). This was a group of young actors, led by DiCaprio, known for tearing up New York and Los Angeles and dating a string of models.
Because of that history, the public is primed to assume the worst. When people see Tobey with a 20-year-old, they don't see a "good guy helping a friend to her car." They see a pattern.
In the weeks following the Hamptons party, Tobey was also spotted in Sardinia with Babette Strijbos, a 24-year-old model. This didn't exactly help quiet the critics. Whether it’s just a mid-life "hot girl summer" or a genuine shift in his dating preferences, the optics definitely keep the tabloids busy.
Why Does This Age Gap Matter?
In 2026, the conversation around age gaps in Hollywood has become much more nuanced. It’s not just about "two consenting adults." People talk about power dynamics, the #MeToo movement’s legacy, and the cultural trend of aging actors seeking out "forever-young" partners.
Critics argue that when a man’s girlfriend is closer in age to his children than to himself, it creates a weird social friction. Tobey’s daughter, Ruby, is 17 (turning 18). Lily Chee was 20 at the time of the photos. That's a three-year difference between his potential date and his child.
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On the flip side, supporters—and people like Jennifer Meyer—argue that celebrities should be allowed to exist in the same space without it being a scandal. If they were just hanging out at a party, is it really anyone's business?
What Really Happened?
So, was it a summer fling or a total misunderstanding?
A source told Us Weekly shortly after the event that the two "aren't seriously dating but have been hanging out." They called it "casual" and noted they were introduced through mutual friends. Since that summer, the "Lily and Tobey" news cycle has mostly died down. Neither of them has posted about each other, and they haven't been seen together in a romantic context since those initial Hamptons shots.
Lily continues to post her high-fashion vlogs and New York City "get ready with me" videos. Tobey remains notoriously private, likely waiting for his next big role or the next Spider-Man reunion rumor to take over the headlines.
Basically, it looks like a classic case of Hamptons-induced frenzy. You put a bunch of famous, attractive people in a mansion with an open bar and white outfits, and the paparazzi are going to find a story whether there is one or not.
What you can take away from this:
- Don't trust every paparazzi angle. A hand on a back can look like a romantic embrace when it's actually just someone navigating a crowded room.
- The "Leo Effect" is real. Tobey will likely always be scrutinized for his dating life because of his proximity to DiCaprio.
- Lily Chee is a star to watch. Regardless of the rumors, she has a massive platform and a legitimate acting career that's only growing.
If you’re looking to follow the "truth" of celebrity relationships, the best place to look isn't the headlines—it's the silence. In Hollywood, when something is real, it eventually goes Instagram official. When it’s just a party rumor, it vanishes into the Hamptons fog.