Tobey Maguire and Kirsten Dunst's Relationship Timeline: A Look Back

Although dating your co-star is nothing new in Hollywood, a movie franchise that constantly churns out romance IRL is worth taking a closer look at. While Zendaya and Tom Holland are the latest superhero-love interest pairing to come out of Spider-Man (with Emma Stone and Andrew Garfield preceding them), the OG Peter Parker and MJ couple is none other than actor and producer Tobey Maguire and Oscar-nominated actress Kirsten Dunst.

After meeting on set in 2001, the Bring It On star and Cider House Rules actor went on to date behind closed doors — at least for the most part — before going their separate ways just a year later. Yet despite their short-lived love affair off-camera, the duo's on-screen presence will forever live on — most notably via their award-winning upside-down kiss. Interestingly, and perhaps also tellingly, the kiss wasn't all it was cracked up to be.

Here's a complete timeline of their relationship.

January 2001: Tobey Maguire and Kirsten Dunst first meet

The pair met on the set of Spider-Man back in 2001. Maguire, of course, played Peter Parker, while Dunst took on the role of Parker's love interest, Mary Jane. Before long, the actors' on-screen chemistry turned into real-life sparks — despite keeping it under wraps. In fact, the co-stars were fully committed to keeping their relationship a secret. Many people — including Spider-Man director Sam Raimi — didn't even know they dated until the breakup.

July 2001: Tobey Maguire and Kirsten Dunst are first spotted together

Clues of the couple's romantic affair began to drop after filming wrapped in June. For starters, they were seen out and about together in Los Angeles by July. Plus, the actors occasionally praised each other during Spider-Man press interviews.

In the May 2002 issue of Vanity Fair, Maguire praised Dunst for her acting ability, telling the outlet, "She's very, very talented. She's very appealing and beautiful. She has a womanly quality but also a very fun girl quality, an innocence. [And] there's no vanity in her acting. She just commits and goes for it."

Meanwhile, when Dunst was asked why she wanted to play Mary Jane, she told Entertainment Weekly that Tobey had something to do with it.

"I wanted to do Spider-Man the minute I found out about it, even before Peter Parker had been cast. But as soon as I learned Tobey [Maguire] was doing it, I wanted to do it even more," she said. "He's so talented and adorable, but more than that, he has an immaculate body of work. I had been wanting to work with him for a long, long time."

2002: Tobey Maguire and Kirsten Dunst break up

Dunst and Maguire split in early 2002 after dating for a little over a year. While they never publicly announced their breakup, a source close to Dunst told Us Weekly at the time that things between them just fizzled out. "It wasn't anything, in particular, that happened," they said. "They'll probably remain friends."

Soon after, Maguire got into a relationship with jewelry designer Jennifer Meyer, and Dunst began dating Jake Gyllenhaal.

The pair remained cordial amid the breakup and went on to film a second Spider-Man movie two years after their split, which, at first, had the film's director concerned. "I actually had some worries about [their breakup]," Raimi told The Sydney Morning Herald. "They apparently began dating with 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."

"They really like each other, I think, very much," he continued. "And that relationship probably just added to their ability to trust each other."

2003: Tobey Maguire and Kirsten Dunst win "Best Kiss" at the MTV Movie & TV Awards

In the first Spider-Man film installment, Peter Parker hung upside down from his spider web after saving Mary Jane, and to thank him, she pulled down his mask halfway and kissed him in the pouring rain. It became an iconic moment in pop culture history, winning Best Kiss at the MTV Movie & TV Awards in 2003.

However, according to both Dunst and Maguire, the kiss wasn't as romantic as one might imagine. 

"There was rain pouring up or down my nose. I couldn't breathe, and I was gasping for breath out of the corner of Kirsten's mouth," Maguire told reporters ahead of the film's premiere in 2002, per The Hollywood Reporter. "Poor girl. I was giving her mouth-to-mouth rather than kissing her. But in the midst of that, I was sneaking some pleasure out of it."

Dunst also reflected on the not-so-sexy moment 20 years later during an interview with W Magazine in January 2022. 

"I did not feel like it was a famous kiss because Tobey was ... Water was getting up his nose because of the rain, and then he couldn't breathe in the Spider-Man suit, and then ... And it just felt very late at night. I didn't think about it that way," she told the outlet. "But the way it was presented to me, Sam gave me this book of famous kisses, so that made me realize how romantic and special Sam wanted this to be."

She added, "Even though it wasn't necessarily feeling that way with Tobey hanging upside down." 

Though, on the big screen, she admitted that it "looked like a great kiss."