Tobey Maguire's Dating History Tobey's Love Life

Tobey Maguire is definitely famous for his roles in Spider-Man, Brothers, The Great Gatsby, The Good German, and to name a few more. But did you know that he’s also famous for keeping his love life private? Ever since achieving stardom after the skyrocketing success of the Spider-Man trilogy, Maguire’s love life has been under the keen scrutiny of the audience, especially after his link-up with Kirsten Dunst, his Spider-Man co-star. Even after his split from his wife, Jennifer Meyer, the public eyes don’t want to seem to take off from Tobey Maguire’s dating life.

Maguire has always maintained silence about his relationships. But that never stops the public from keeping a list of all the incredible women he’s been with.

Here’s a glimpse of Tobey Maguire’s dating history.

Sara Gilbert1993-1996
Rashida Jones1997-2000
Kirsten Dunst2001-2002
Demi Moore2002
Jennifer Meyer (married)2003-2016
Tatiana Dieteman2018-2022

Sara Gilbert

Back when Maguire’s career was taking its baby steps, Sara Gilbert and Tobey Maguire were a thing. Yes, Sara Gilbert, who is best known for playing Darlene Conner on the Tv show Roseanne. They met during the mid-90s and quickly took off. The couple was together from 1993 to 1996. Although both sides have kept quiet about the breakup, the split was definitely amicable, as both of them remain good friends to date. In fact, Maguire let her, Ali Aider, and their child stay at his house while their house was getting renovated in 2005. Clearly, Tobey’s love and care for Sara go beyond the usual friendships.

Rashida Jones

Did we know that Rashida Jones and Tobey Maguire were a couple for almost three years? Nope, we did not. Rashida Jones and Tobey Maguire, the forgotten couple.  Apparently, the couple was so deeply in love that there were rumors of them being engaged.

Jones may be well known for her role in The Office as Karen Filippelli, but nobody knew about her link-up with Maguire due to Maguire’s tendency to keep his dating life a secret. Although their relationship was kept under wraps for quite some time, this doesn’t mean that we can pass their relationship as a fling. The couple did date from 1997 to 2000 and were irrecoverably in love with each other. So much so that there were rumors of them being engaged. Little is known about Maguire’s link-up with Rashida Jones as they’ve both never publicly spoken about it.

Kirsten Dunst

Kirsten Dunst. The one and only girlfriend that our friendly neighborhood Spider-Man couldn’t hide from the prying eyes of the beloved public. Maguire and Dunst started dating whilst filming Spider-Man in 2001. Their love for each other oozed through their chemistry on-screen. After all, who didn’t love watching them together on-screen? It was a real treat for fans when rumors of their link-up started to spread. Sadly, their love wasn’t made in heaven as the pair broke up in early 2002, leaving fans shattered.

While Dunst and Maguire denied any rumors of their relationship, director Sam Raimi admitted in an interview that he found out about them after the filming of Spider-Man. Even co-star James Franco couldn’t stop himself from gushing about them.  “Tobey and Kirsten became a couple around that time. I had a crush on Kirsten around that time, and I think I was upset about that as well…..Tobey was mad at me for a while. By the second film, we were cool,” says Franco.

While Mary Jane Watson and Peter Parker were an endgame, sadly, Tobey Maguire and Kirsten Dunst weren’t.

Demi Moore

Shortly after his split with Dunst, Maguire was rumored to be involved with Demi Moore in 2002. What was only a brief fling could have blossomed into a loving relationship had Moore not said her vows to Ashton Kutcher.

They were briefly together, but even long after splitting up, Moore supposedly still continues to harbor hopes for them. The Charlie’s Angels actress is an absolute romantic at heart. After her split with Kutcher, Moore allegedly reached out to Maguire, hoping to rekindle their lost romance. A source close to Moore says, “Demi is still a sexy, attractive woman, and Tobey is just her type -younger, smart, and kind of goofy”. This also happens to be after Maguire’s separation from Jennifer Meyer (who we’ll talk about very soon).

Well, all things fall into place soon enough as Demi is currently dating chef Daniel Humm and we hope she’s finally found the love of her life.

Jennifer Meyer

Maguire may have had a string of unlucky romances, but love did come knocking at his door sooner than he expected. Maguire met Jennifer Meyer, a jewelry designer, in 2003 and soon started dating. Their sweet romance blossomed, and soon they got married in 2007 and welcomed two beautiful kids together, Ruby Sweetheart Maguire, born in 2006 and Otis Tobias Maguire, born in 2009. Maguire may be reticent to speak about his marital life but their marriage was too warm-hearted to be avoided by the public. Meyer also contributed to Spider-Man 3 by designing a heart-shaped locket that Maguire’s character’s love interest wears.

Alas, all that starts well doesn’t always end up well. In 2016, it was reported that Maguire and Meyer had separated amicably. They chose to remain good friends and “devoted parents”, as a source close to the couple puts it.  In 2020, Meyer filed for divorce.

Both sides have maintained silence over the separation(as expected from Maguire) but a source close to Maguire has interesting things to say.  “They have completely different interests and haven’t seemed to be connecting,” the source said to PEOPLE magazine. “He’s extremely private and prefers to stay home, and she’s very social and has tons of girlfriends.”
But life never stops. You loved someone, you broke up and now move on. You’ll find love again.

Tatiana Dieteman

It seems as if Maguire hasn’t given up on love at all. He soon found love in a model, Tatiana Dieteman. They started dating in 2018 and were going well for solid three years but soon broke up in early 2022. Although no comments have been made from both side, fans speculated their 18-year age gap to be the issue.

But it seems Tatiana has found love in her life again. What once started off as a rumor soon became a reality after Dieteman confirmed her break up with Maguire and current relationship by reposting her now boyfriend, pro surfer Koa Smith’s post on Instagram dedicated to her on Valentine’s Day.

Maguire’s dating history may keep us entertained but we wish all the best for him and hope that he finds love in his life. Life comes with its share of ups and downs, and Maguire is also facing such ups and downs in his love life. But life is bigger and should be experienced from all aspects. We wish all the love to Tobey. Let us hope that the Brothers actor finds his perfect life partner. Fingers crossed !!

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Al Amin Sagor is simply a movie freak who is passionate about writing entertainment content. He loves to watch web series, and movies and write on celebrity gossip or trendy movie news. He also covers media and entertainment news on various online platforms. He is one of the "Jewel" of The News Titan.


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