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, News47.us has rounded up a list of Tobey’s confirmed romances over the years, from his past marriage to long-term relationships.
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.”
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.
