Apparently, that iconic upside-down kiss wasn't as romantic as it looks.
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Tobey Maguire, Kirsten Dunst
Tobey Maguire, Kirsten Dunst
| Credit: Jeff Kravitz/FilmMagic

Who: Actress Kirsten Dunst, 39, and actor and producer Tobey Macguire, 46. 

How They Met: Kirsten and Tobey 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. 

Why We Loved Them: They were fully committed to keeping their relationship under wraps. In fact, many people — including Spider-Man director Sam Raimi — didn't even know they dated until the breakup. However, they did occasionally gush about 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 by Entertainment Weekly why she wanted to play Mary Jane, she admitted 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."

Spiderman and Kirsten Dunst in a scene from the film 'Spiderman', 2002.
Credit: Photo by Columbia Pictures/Getty Images

When They Peaked: Two words: upside-down kiss. 

In the first Spider-Man, 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. And it even won Best Kiss at the MTV Movie Awards in 2003. 

But 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," Tobey told reporters ahead of the film's premiere in 2002. "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."

Kirsten also reflected on the not-so-sexy moment twenty 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 explained. "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."

The Breakup: Dunst and Maguire split in early 2002 after dating for a little more than a year. While there wasn't a breakup statement, 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."

Where They Are Now: Kirsten is engaged to her former Fargo co-star Jesse Plemons and the couple shares two children together — Ennis Howard, 3, and 11-month-old James Robert. 

Most recently, Dunst was nominated for an Oscar for her role in the film The Power of the Dog, as was her fiancé Plemons, who also starred in the romantic drama. Sadly, neither took home an award, but Kirsten has already moved on to her next project and began filming Civil War

Tobey went on to marry Jennifer Meyer in 2007, but the pair — who share two children, Ruby Sweetheart, 15, and Otis Tobias, 12 — split nine years later. Maguire's latest relationship was with model Tatiana Dieteman before the two called it quits in February.

After a brief break from acting, Maguire returned to the spotlight and reprised his role as Peter Parker with a cameo in Spider-Man: No Way Home in 2021. The actor has also joined the cast of Apple TV+'s climate change anthology drama series Extrapolations

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.