All 3 “Spider-Man” Actors Have Dated Their Leading Ladies! A Look at Their Romances On and Off Screen

Spider-Man may not be a romance, but it's brought a number of love stories to life.

Three actors — Tobey Maguire, Andrew Garfield and Tom 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.

In the comics, Spider-Man has a relationship with Mary Jane Watson, or MJ, and with Gwen Stacy, depending on the iteration. In Maguire and Holland's franchises, the titular character falls for Mary Jane (played by Kirsten Dunst in Maguire's trilogy and Zendaya in Holland's), while Garfield's two films see him in love with Gwen (Emma Stone).

Related: Where to Watch All of the Spider-Man Movies

Though all three actors dated their respective counterparts during shooting (and beyond), only one Spider-Man couple has stood the test of time: Holland and Zendaya got engaged in December 2024 after several years together.

From connecting on the sets of Spider-Man to the fate of their relationships, here's everything to know about the three Spider-Man actors and their relationships with their leading ladies.

Tobey Maguire and Kirsten Dunst

Maguire was cast as Spider-Man in the Sam Raimi trilogy in 2000 and proceeded to star in 2002's Spider-Man, 2004's Spider-Man 2 and 2007's Spider-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, tell Entertainment Weekly in April 2002 that she was in part drawn to the Spider-Man movies because of Maguire.

"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."

However, by early 2002, Dunst and Maguire's romance had fizzled out, and the two had an amicable breakup. Raimi admitted in a May 2007 interview with the Sydney Morning Herald that he was initially worried about how their relationship ending would affect their chemistry on set — but the two were professionals, he said.

"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

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 first The 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 told ABC News of working with Garfield again on 2014's The Amazing Spider-Man 2. "I love him very much."

Related: Emma Stone and Andrew Garfield's Relationship: A Look Back

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 of Angels in America in May 2017 and Garfield attending the London premiere of Stone's movie Poor Things in December 2023.

The pair reunited again at the 2025 Golden Globe Awards in a sweet moment on the red carpet alongside Stone's husband, Dave McCary.

Tom Holland and Zendaya

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's Spider-Man: Homecoming, 2019's Spider-Man: Far From Home and 2021's Spider-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 were spotted kissing in a car four years later in July 2021.

Two months later, they went Instagram official, with Holland wishing Zendaya a happy 25th birthday in a sweet post in 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.

Related: Zendaya and Tom Holland's Relationship Timeline

“Our relationship is something that we are incredibly protective of and we want to keep as sacred as possible," Holland told The Hollywood Reporter in 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.”

The two have quietly shown up in support of one another, despite rarely walking red carpets together. In August 2024, Zendaya attended Holland's final night as Romeo in London's West End production of Romeo & Juliet, gifting him with a bouquet of flowers. Two months later, she was by his side at launch of his non-alcoholic drink brand, Bero, in New York City.

At the 2025 Golden Globe Awards in January, Zendaya sparked engagement rumors when she walked the carpet with a ring on her left finger. Less than a day later, PEOPLE confirmed the actors were recently engaged.

Next, the two will star together in director Christopher Nolan's next movie: an adaptation of The Odyssey.

Read the original article on People