All 3Spider-ManActors Have Dated Their Leading Ladies! A Look at Their Romances On and Off Screen

Mar. 15, 2025

Zendaya as MJ and Tom Holland as Peter Parker/Spider-Man ‘Spider-Man: Far from Home’ Film - 2019; Tobey Maguire, Kirsten Dunst Spiderman - 2002.Photo:J Whilden/Columbia/Marvel/Kobal/Shutterstock; Columbia/Marvel/Kobal/Shutterstock

J Whilden/Columbia/Marvel/Kobal/Shutterstock; Columbia/Marvel/Kobal/Shutterstock

Spider-Manmay not be a romance, but it’s brought a number of love stories to life.

Three actors —Tobey Maguire,Andrew GarfieldandTom Holland— have played Spider-Man in major movie adaptations of the beloved comic — and all three of them have found dated their romantic counterparts in the movie.

Though all three actors dated their respective counterparts during shooting (and beyond), only oneSpider-Mancouple has stood the test of time: Holland and Zendayagot engagedin December 2024 after several years together.

From connecting on the sets ofSpider-Manto the fate of their relationships, here’s everything to know about the threeSpider-Manactors and their relationships with their leading ladies.

Tobey Maguire and Kirsten Dunst

Tobey Maguire and Kirsten Dunst at the “Spider-Man 2” London premiere ; Tobey Maguire as Spider-Man and Kirsten Dunst as Mary Jane in ‘Spider-Man 2’.Fred Duval/FilmMagic; Melissa Moseley/Marvel/Sony/Kobal/Shutterstock

Fred Duval/FilmMagic; Melissa Moseley/Marvel/Sony/Kobal/Shutterstock

Maguire was cast as Spider-Man in theSam Raimitrilogy in 2000 and proceeded to star in 2002’sSpider-Man, 2004’sSpider-Man 2and 2007’sSpider-Man 3. Dunst starred as Mary Jane, Peter Parker’s love interest, alongside him in all three films.

The two started dating in real life while filming the first movie in 2001. However, they were committed to keeping their relationship a secret — so much so that even Raimi didn’t know they were dating until they broke up.

Maguire and Dunst were first spotted together after filming wrapped in July 2001, but never commented publicly on their relationship. Dunst did, however, tellEntertainment Weeklyin April 2002 that she was in part drawn to theSpider-Manmovies because of Maguire.

“I wanted to doSpider-Manthe 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.”

“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,” Raimi said. “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 said. “And that relationship probably just added to their ability to trust each other.”

Andrew Garfield and Emma Stone

Emma Stone and Andrew Garfield attend ‘The Amazing Spider-Man 2’ world premiere ; Andrew Garfield as Peter Parker and Emma Stone as Gwen Stacy in ‘The Amazing Spider-Man’.Gareth Cattermole/Getty; Columbia/Kobal/Shutterstock

Gareth Cattermole/Getty; Columbia/Kobal/Shutterstock

Garfield stepped into the role of Spider-Man in December 2010, with Stone taking on his love interest from a different iteration of the comics, Gwen Stacy. Though it is unclear exactly when the two began dating, they met while filming the firstThe Amazing Spider-Man.

Stone and Garfield were first spotted on a date in November 2011, grabbing coffee at Starbucks after watching a movie together in Los Angeles. While the couple kept their relationship lowkey, they were seen on a number of dates in the four years they were together and spoke fondly of one another during their press tours.

“It’s like a dream to work with him. He’s obviously one of the greatest actors I think we have alive today and he’s also just a remarkable human being,” Stone toldABC Newsof working with Garfield again on 2014’sThe Amazing Spider-Man 2. “I love him very much.”

However, in April 2015, the two split up. After a brief reconciliation in May, the two called it quits for the final time in October that year. “They still have love for one another,” a source told PEOPLE at the time. “They are on good terms with each other and remain close.”

In the years since their relationship, Garfield and Stone have been vocal about their continued friendship and have shown up in support of one another at their various projects, with Stone attending Garfield’s West End production ofAngels in Americain May 2017 and Garfield attending the London premiere of Stone’s moviePoor Thingsin December 2023.

The pairreunited again at the 2025 Golden Globe Awardsin a sweet moment on the red carpet alongside Stone’s husband,Dave McCary.

Tom Holland and Zendaya

Tom Holland and Zendaya at the “Spider-Man: No Way Home” Los Angeles premiere on Dec. 13, 2021 ; Tom Holland as Spider-Man and Zendaya as MJ in ‘Spider-Man: Far From Home’.Emma McIntyre/Getty; Sony Pictures

Emma McIntyre/Getty; Sony Pictures

Holland became the latest actor to helm the Spider-Man title when he took on the role in 2016, with Zendaya cast opposite him as the new MJ. Peter and MJ’s relationship unfolded on screen over the course of three movies, while Holland and Zendaya’s grew simultaneously.

The two starred together in 2017’sSpider-Man: Homecoming, 2019’sSpider-Man: Far From Homeand 2021’sSpider-Man: No Way Home. While there were rumors surrounding their relationship as early as July 2017, the two didn’t confirm their relationship until they werespotted kissing in a carfour years later in July 2021.

Two months later, theywent Instagram official, with Holland wishing Zendaya a happy 25th birthday in asweet postin which he called her “My MJ.”

Since confirming they were dating, both have spoken about wanting to keep their relationship private — something they found challenging due to their careers.

“Our relationship is something that we are incredibly protective of and we want to keep as sacred as possible," Holland toldThe Hollywood Reporterin June 2023. “We don’t think that we owe it to anyone, it’s our thing, and it has nothing to do with our careers.”

At the 2025 Golden Globe Awards in January, Zendayasparked engagement rumorswhen she walked the carpet with a ring on her left finger. Less than a day later, PEOPLE confirmed theactors were recently engaged.

Next, the twowill star togetherin directorChristopher Nolan’s next movie:an adaptation ofThe Odyssey.

source: people.com