Tobey Maguire Fuels Dating Rumors With 20-Year-Old Model Lily Chee

Split image of Tobey Maguire and Lily Chee
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Tobey Maguire has just turned 49, yet he has been seen “casually” hanging out with a 20-year-old model as of late.

After Michael Rubin‘s star-studded 4th of July White Party in The Hamptons on Thursday, it seems as though former Spiderman has found himself in a web of a situation.

At the event, where his close friend 49-year-old Leonardo DiCaprio was also seen, the fellow 49-year-old Tobey Maguire was photographed with his arm around 20-year-old Lily Chee.

“They aren’t seriously dating but have been hanging out,” a source exclusively tells Us Weekly about the “very casual” situation between the ‘non-couple’.

“Tobey knew Lily and her girlfriends were invited to the party and they planned to hangout and meet up,” the source continued. “He was introduced to her through [businessman] Richie Akiva and mutual friends.”

Richie Akiva is known as a nightclub tycoon in New York, where the young model and actress is based. Chee just celebrated her 20th birthday in September 2023. Her acting credits include an appearance in a 2016 episode of Netflix’s Daredevil superhero series. She has also appeared on The Other Two, New Amsterdam and two Tubi series, Zoe Valentine and Chicken Girls. Chee last appeared in the short film titled Nothing, Except Everything.

Previously, Maguire was linked to model and designer Tatiana Dieteman, 32, who he dated for three years until they called it quits in 2022. They first started dating when Dieteman was 27 and Maguire was 44 in 2018. The two reportedly met at a party hosted by Leonardo DiCaprio.

Amidst all the dating speculation, one of Maguire’s biggest supporters and ex-wife has been vocal about their close and loving relationship. Maguire and Jennifer Meyer, 42, were married in 2007 before announcing their separation nine years later in 2016. The jewelry designer didn’t file for divorce from Maguire until October 2020, requesting joint legal and physical custody of their two children: daughter Ruby, born November 2006, and son Otis, born May 2009.”

The former couple have since maintained an amicable co-parenting relationship. In 2022, Meyer shared on an episode of The World’s First Podcast that her divorce from Maguire has been “the most beautiful experience of my life”.

“I would literally do anything in the world for Tobey. He is my brother. I love him to death and we have the most beautiful family,” Meyer told podcast co-hosts Sara and Erin Foster at the time. “The work is a motherf***er. I’m not gonna lie. And we did a lot of work to stay on track to stay a family.

“It was a choice and it was trusting in, like, the universe has got our back,” she said.

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