Tobey Maguire is one of Hollywood’s most private celebrities, especially when it comes to his relationships. Despite being one of the film industry’s most popular names, thanks to the Spider-Man franchise, the Great Gatsby actor rarely ever comments on his personal life.
But his dating history became a major topic of discussion in July 2026 when a false rumor surfaced about him and Ice Spice kissing at a party. However, a rep for Ice Spice denied the kissing speculation and said the two were just sharing a vape and talking.
Below, Hollywood Life has rounded up a list of Tobey’s confirmed romances over the years, from his past marriage to long-term relationships.
Kirsten Dunst
One of Tobey’s most high-profile relationships was with his Spider-Man co-star Kirsten Dunst, who played his on-screen love interest, Mary “MJ” Watson. The duo dated for about a year from 2001 to 2002.
Although neither actor revealed the reason behind their split, Kirsten described the Spider-Man franchise salary gap between her and her ex-boyfriend during a 2021 interview with The Independent.
“The pay disparity between me and Spider-Man was very extreme,” she said at the time. “I didn’t even think about it. I was just like, ‘Oh yeah, Tobey [Maguire] is playing Spider-Man.’ … But you know who was on the cover of the second Spider-Man poster? Spider-Man and ME.”
Jennifer Meyer
Tobey’s longest relationship was with his ex-wife, Jennifer Meyer. The couple got married in 2007 and went on to welcome their children, son Otis and daughter Ruby, together.
In 2016, Jennifer and Tobey separated. At the time, an insider told People that the ex-couple had been “living separate lives for a while.”
“They have completely different interests and haven’t seemed to be connecting,” the source explained. “He’s extremely private and prefers to stay home, and she’s very social and has tons of girlfriends. … They haven’t been happy together for a long time, but they are great parents and they love their children.”
Eventually, in 2020, Tobey and Jennifer finalized their divorce, and they’ve remained amicable co-parents to their kids. In fact, Tobey officiated Jennifer’s 2026 wedding to her new husband, Geoff Ogunlesi.
Tatiana Dieteman
From 2018 to 2019, Tobey dated model Tatiana Dieteman. They kept their relationship away from the spotlight as much as possible, so the only way their breakup became public knowledge was when she shared pictures from her new romance with surfer Koa Smith in early 2022.
Ice Spice
Ice Spice and Tobey were believed to have been spotted kissing at a party just before the July 4th holiday weekend in 2026. However, her team shut down the rumors and said the pair were just sharing a vape.
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