Tobey Maguire's girlfriend history includes several high-profile relationships, such as those with Rashida Jones, Tatiana Dieteman, and Kirsten Dunst. The Spider-Man actor was also married once to Jennifer Meyer, with whom he shares two children. As of May 2026, Tobey is rumored to be in a relationship with Mishka Silva, a model and influencer.
Key Takeaways
- Tobey Maguire's first public romantic relationship was in 1997 with actress Rashida Jones.
- Between 2007 and 2016, he was married to Jennifer Meyer, a jewelry designer.
- Maguire's children, Ruby Sweetheart Maguire and Otis Tobias Maguire, were born in 2006 and 2009, respectively.
- From 2018 to 2022, Tobey Maguire dated Tatiana Dieteman.
Profile Summary
- Full Name: Tobias Vincent Maguire
- Gender: Male
- Date of Birth: 27 June 1975
- Age: 50 years (as of May 2026)
- Zodiac Sign: Cancer
- Place of Birth: Santa Monica, California, United States
- Residence: Brentwood, Los Angeles, California, United States
- Nationality: American
- Ethnicity: White
- Weight: 71 kg (155 lbs)
- Height: 173 cm (5'8")
- Eye Color: Blue
- Hair Color: Dark brown
- Father: Vincent Maguire
- Mother: Wendy Brown
- Siblings: 5
- Relationship Status: Dating
- Partner: Mishka Silva
- Profession: Actor, film producer
- Net Worth: $75 million
Tobey Maguire's Girlfriends Over the Years
In February 2026, Tobey Maguire was seen at Super Bowl LX with Mishka Silva, sparking rumors of a relationship. At the time of this writing, neither Maguire nor Silva has confirmed the rumor. Here are the details of Tobey Maguire's girlfriend timeline.
Rashida Jones (1997–1999)
According to Page Six, Tobey Maguire and Rashida Jones dated between 1997 and 1999. Although she is rumored to have been engaged to him, neither has publicly confirmed the relationship or an engagement. In an interview with The Guardian, Rashida shared her views on relationships at a young age: "I had the full princess fantasy: the white horse, the whole being saved from my life, which is ridiculous. What do I want to be saved from?"
Kirsten Dunst (2001–2002)
Tobey Maguire and Kirsten Dunst shared a two-year relationship between 2001 and 2002. Kirsten has been romantically linked to Mark Ronson and Adam Brody, whom she dated in 2007. Tobey and Kirsten met on set and began their off-screen romance while filming the first Spider-Man movie, released in 2002. A year later, the couple, who played Peter Parker and Mary Jane, won the Best Kiss at the MTV Movie and TV Awards. In an interview with The Sydney Morning Herald, the film's director, Sam Raimi, confirmed the relationship, adding that it was a source of worry during filming: "They apparently began dating each other, I think, in the middle of the first movie ... although I didn't know it at the time ... but definitely they eventually broke up before the second movie. I was concerned they wouldn't get the same chemistry back, but it was just me worrying." A source close to the couple later spoke about their breakup to Us Weekly, as recorded by In Style: "It wasn't anything in particular that happened. They'll probably remain friends."
Tatiana Dieteman (2018–2022)
Tatiana Dieteman and Tobey Maguire were romantically linked for three years between 2018 and 2022. The couple began dating after Maguire's divorce. They were first spotted in August 2018 at a party for Leonardo DiCaprio. In November 2018, Page Six reported that the Pawn Sacrifice actor had been spotted ring shopping with his girlfriend. The outlet confirmed that the rings were everyday diamond rings and not engagement rings. In 2022, Tatiana confirmed their breakup and a new romance in a now-deleted Instagram post, captioned: "Happy Valentine's Day to my bessss fwennnnnn!!! Love you, baby!" An insider close to Tatiana simply told E! News: "Tatiana has moved on."
Lily Chee (2024)
In July 2024, Tobey Maguire went viral after a photo of him with model and actress Lily Chee was released. Paparazzi captured the two walking hand in hand during Michael Rubin's all-white Fourth of July party. In attendance were Tobey's fellow A-listers: Tom Brady, Mary J. Blige, Lil Wayne, Jay-Z, Kim Kardashian, Drake, Teyana Taylor, and Coco Jones, among others. Despite the speculation and controversy over the age difference between Tobey Maguire and Lily Chee, neither has publicly commented on the relationship. To dispel the rumors, Tobey's ex-wife, Jennifer Meyer, took to social media, hitting back at comments about the photo, as recorded by Page Six. She said: "I don't usually respond to such nonsense, but he was kindly helping a friend to her car. And now he is being blasted online for dating someone he is not." She added: "I'm disengaging after this.... But don't believe everything you read (I'm sure we were taught that somewhere). Tobey is as good a guy as it gets."
Mishka Silva (2026)
Tobey Maguire and Mishka Silva were first seen together during Super Bowl LX at Levi's Stadium in Santa Clara. The pair was seated in the cozy VIP section. Mishka is a young social media influencer and model known for her content. The sighting sparked immediate speculation, with online discussions focusing on the 30-year age gap between the two.
Who Is Tobey Maguire's Ex-Wife, Jennifer Meyer?
Jennifer Meyer is a well-known jeweler whose pieces have been worn by Jennifer Aniston, Kate Hudson, Reese Witherspoon, and Selena Gomez. Tobey Maguire met his former wife, Jennifer Meyer, in 2003 while he was filming Seabiscuit. They dated for three years until they got engaged and welcomed their first child, Ruby Sweetheart Maguire, in 2006. Maguire and Meyer tied the knot in September 2007 at a private ceremony in Kona, Hawaii. Their second child, Otis Tobias Maguire, was born two years later, in May 2009. In October 2016, the couple released a joint statement announcing their separation after nine years of marriage. The statement, shared exclusively with People, partly read: "After much soul-searching and consideration, we have made the decision to separate as a couple. As devoted parents, our first priority remains raising our children together with enduring love, respect, and friendship." Three years later, an insider updated the outlet on the state of the separation: "They've been living separate lives for a while. They have completely different interests and haven't seemed to be connecting... They haven't been happy together for a long time. But they are great parents, and they love their children."
FAQs
- Who is Tobey Maguire in a relationship with? The Wonders Boys actor is rumored to be in a relationship with Mishka Silva.
- Who is Tatiana Dieteman? Dieteman is an American model who dated Tobey Maguire between 2018 and 2022.
- Who is Mishka Silva? Mishka Silva is an American actress, model, singer, and internet personality known for her appearance in The White Shoes and Steve Madden: Never Miss a Summer.
- Did Tobey Maguire and Rashida Jones date? The Hollywood actors had a relationship in the late 1990s.
- Did Tobey Maguire and Kirsten Dunst date? The American actors dated for about a year between 2001 and 2002 while filming Spider-Man.
- What happened between Tobey Maguire and Kirsten Dunst? The pair broke up in 2002.
- How many children does Tobey Maguire have? The Joyride actor has two children, Ruby Sweetheart and Otis Tobias Maguire, with his ex-wife, Jennifer Meyer.
Tobey Maguire's girlfriend timeline began with a two-year pre-fame relationship with Rashida Jones and an on-set romance with Kirsten Dunst. Following his divorce, he dated Tatiana Dieteman and had an unconfirmed relationship with Lily Chee. He is currently believed to be in a relationship with Mishka Silva.
