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Tobey Maguire is widely known for defining a generation of superhero cinema through his iconic role of Spider-Man in Sam Raimi’s movies. However, the actor has always tried to keep his personal life relatively private. Over the past years, he has been in several short-term and long-term relationships, ranging from film co-stars to long-term partners. While some relationships are confirmed, others remain speculations, highlighting how celebrity dating life often blurs facts and gossip. Here we have listed the relationship timeline of the Marvel star.
Rashida Jones
Tobey Maguire and actress Rashida Jones started dating in 1997, which was way before he attained global fame and stardom. Apparently, their relationship was quite serious, and as per reports, they were also once engaged. However, the duo separated after three years, in 2000.
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Kirsten Dunst
Romance started blooming between Maguire and Hollywood diva Kirsten Dunst when they were filming Spider-Man in 2001. The couple played the main leads of the film. Their relationship was short-lived, as the duo parted ways after a year. The duo maintained a friendly relationship while they worked together on future projects.
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Jennifer Meyer
Tobey Maguire met jewelry designer Jennifer Meyer in 2003, during the shoot days of the film Seabiscuit. They dated for a few years and got engaged in 2006. The couple tied the knot in 2007 at a private ceremony in Kona, Hawaii. They had two children, a daughter in 2006 and a son in 2009. The couple officially separated in 2016; however, their divorce was finalized in 2020.
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Tatiana Dieteman
After his separation from Meyer, the Spider-Man star started dating model Tatiana Dieteman in 2018. The couple met at a party, and a romantic relationship developed between them. The pair was together for three years and broke up in early 2022. The duo shares an amicable bond.
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Lily Chee
Tobey Maguire came to the spotlight in 2024, when his dating rumors started making rounds. The actor was spotted with model and actress Lily Chee at a high-profile party. However, his ex-wife, Jennifer Meyer, made a public statement that he was not dating the model and was only helping her as a friend.
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Mishka Silva
Tobey Maguire is again making the headlines for his dating life in 2026. The actor was spotted at the Super Bowl with his rumored girlfriend, Mishka Silva. She is a young 20-year-old model and influencer. Maguire was photographed with her; however, there is no confirmation about the relationship.
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