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People Are Grossed Out After Finding Out Who Tobey Maguire Is Dating
Fans are horrified after finding out who Tobey Maguire is dating.
If you grew up in the early 2000s, Tobey Maguire was the guy – the awkward, lovable Peter Parker swung through New York City in Sam Raimi’s Spider-Man trilogy and became one of Hollywood’s most recognizable faces overnight.
The first film, released in 2002, broke box office records and launched a franchise that defined a generation of superhero cinema.
Maguire was charming, self-deprecating, and had a boy-next-door quality that made him impossible not to root for. He was Spider-Man. He was everyone’s favorite nerd turned hero.
But that was then. These days, Maguire is making headlines for very different reasons, and the internet is not happy about it.
A long pattern…
Now 50, Maguire has developed a well-documented pattern of dating significantly younger women in the years since his split from jewellery designer Jennifer Meyer in 2016, with whom he shares two children.
From 2018 to 2021, he dated model Tatiana Dieteman, who is 17 years his junior. In 2024, he was linked to model Lily Chee when she was just 20 years old, and was also photographed kissing model Babette Strijbos, who is 25 years younger than him, Yahoo reports.
The trend hasn’t gone unnoticed, and it’s hard not to draw comparisons to his longtime best friend Leonardo DiCaprio, who has long been notorious for his own preference for dating women in their early twenties.
‘The P***y Posse’
The Maguire-DiCaprio friendship goes way back, all the way to the wild, hedonistic days of late-1990s Hollywood, when the two formed part of an infamous social group alongside actors like Lukas Haas and Kevin Connolly, per Far Out.
Fresh off the runaway success of Titanic, DiCaprio led the group on a prolonged party crawl through New York City that became the stuff of Hollywood legend.
Their well-documented pursuit of women earned them a nickname that was crude, blunt, and, by most accounts, fairly accurate: the P***y Posse.
The group was known for crashing Victoria’s Secret events, setting off stink bombs in upscale bars, and dumping litter off the Brooklyn Promenade.
Their antics were laddish at best and troubling at worst, reaching a low point with the production of Don’s Plum, a film so steeped in misogyny that DiCaprio and Maguire eventually used their Hollywood clout to block its release in the US and Canada.
A lawsuit from producer David Stutman alleged that Maguire, in particular, was concerned the film revealed personal tendencies that would damage his carefully managed public image. A settlement was eventually reached. The film remains largely unseen by American audiences.
The time he got mixed up with a footballer
Not all Maguire-related stories are quite so dark, of course.
In 2022, a rather delightful anecdote emerged from Coachella, when Love Island star Lucinda Strafford reportedly spent an entire evening referring to Maguire as Harry Maguire, the England international center-back, Grazia reports.
To be fair to Strafford, one is a former Hollywood heartthrob best known for wearing a red and blue spandex suit, and the other is a professional footballer. Easy mistake.
Love Island winner Millie Court apparently shared a video of the mix-up in which she could be heard explaining: “Tobey Maguire asked for Lucinda’s number. If you don’t know who he is, he was the original Spider-Man and she’s been calling him Harry Maguire this whole time.” Iconic, honestly.
So, who is Tobey Maguire dating now?
Which brings us to the present, and the reason the internet has collectively shuddered.
Maguire was spotted at the 2026 Super Bowl with model and influencer Mishka Silva.
The pair sparked immediate dating rumors, and once people started looking into who Silva actually is, the reaction was swift and largely one of outrage.
Silva, a Mexican model known for her campaigns with Steve Madden, Smashbox, and Guess, was born on April 8, 2005. She is 20 years old.
Why people are finding this hard to stomach
Here’s where it gets especially uncomfortable.
Maguire has a daughter, Ruby Sweetheart Maguire, born on November 10, 2006, with his ex-wife Jennifer Meyer.
That means his reported new girlfriend Mishka Silva is just one year older than his own daughter.
Reactions online ranged from baffled to outright appalled.
One user on X (formerly Twitter) wrote: “You’d think this is Tobey Maguire and his daughter at the Super Bowl, but it’s his 20-year-old girlfriend.
“She wasn’t even born when the first Spider-Man movie came out. I have clothing in my closet older than her.”
Another pointed out: “His daughter is only one year younger than this girl. She was a year old when his last Spider-Man movie came out.”
It’s a grim milestone, even by the standards of Hollywood’s long history of older men dating dramatically younger women. Spider-Man would not approve.
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