In every Spider-Man movie, Peter Parker and Mj or Gwen Stacy (depending on the universe) have fallen in love. When making the movies, the casting director must have put quite some thought into the chemistry of the two leading roles, because it has brought the actors that play the characters closer together in every generation of the movies that has come out! Of the three generations, only one Spidey couple has gone as far as engagement, which is Tom Holland and Zendaya, who announced their engagement last December. What made this couple break the canon of the breakup trend? As February is the month holding Valentines Day and the new Spider-Man movie is having its first shooting this summer, let’s take a dive into the romance of the dating history of every Spider-Man actor and their love interest!

TOBEY MAGUIRE AND KIRSTEN DUNST

Maguire and Dunst got together during the making of the first Spider-Man movie in 2001, and broke up somewhere while making the second movie in 2002. When filming the scenes, the chemistry they had acting together ended up being more than just a movie. While the couple were only together for about a year, they kept the relationship a secret, a secret kept so well that the Spider-Man director, Sam Raimi, didn’t even know they dated until they broke up!

People first spotted them together in LA a little after the premiere of the first movie. They also made their liking to each other widely known with the compliments that they gave each other during interviews, like Maguire calling Dunst “beautiful,” “talented,” and “appealing” in an interview for the Vanity Fair. 

Then a year later, they split up. Dunst had told US Weekly that “things had just fizzled out.” They most likely stayed friends after that. After finding out about this, the director started to worry about their chemistry fading when filming the next movie.

 “I was concerned they wouldn’t get the same chemistry back, but it was just me worrying.” Raimi told The Sydney Morning Herald. 

He certainly was, because the actors handled it like the pros they are, not letting their life affect Peter’s and MJ’s and had created a movie that grossed about 790 million dollars worldwide.

ANDREW GARFIELD AND EMMA STONE

Garfield and Stone dated from about 2011 to 2015. In that four year period, they were known to be the cutest couple to take the red carpet in Hollywood. 

Like Maguire and Dunst, they tried to keep their relationship a secret. their finding out was inevitable however, as sightings of them together were quite common. In 2015, the couple decided to “go on a break,” and broke up later that year. Despite rumors of reconciliation arising from sightings of them together some time after, Stone got engaged with Saturday Night Live Host Dave McCary, officially ending any suspicions involving the beloved Spider-Man couple getting back together.

Some sources reported that Garfield had cheated on Stone while filming “Silence” in Taiwan, claiming that he had met a girl in a bar and had gone through a “one night stand.” While this information was not confirmed by either actor, Garfield was definitely in a dark place coming back from that shooting. People reported him being distant and cold, and that he hadn’t talked to Stone at all during the filming process. 

To this day, Andrew Garfield and Emma Stone remain close friends, and still support each other. Stone attended Garfield’s West End production of Angels in America, Garfield attended the London premiere of Stone’s movie Poor Things and was seen at the 2025 Golden Globes, cheering on Stone alongside her husband. 

TOM HOLLAND AND ZENDAYA

Zendaya is an actress that started off on the Disney Channel. The young teen had made a promise to not kiss anyone on television until she experienced her first one off camera and away from publicity, which was proving difficult with her filming the show “Shake It Up” at the time. However, later in July 2016, Zendaya and Holland met on the set of “Spider-Man: Homecoming,” which was released that following year. 

While they denied any romantic feelings for each other for many years, in the makings of “Spider-Man: No Way Home” in 2021, they were spotted sharing a kiss in Holland’s car while stopped at a red light, confirming that they were together. Now towards the present at the Golden Globes, Zendaya was seen with a five carat diamond ring on her left hand, which sparked fans to believe that something had happened while the couple was on vacation over the holidays. TMZ and People later announced that they were officially engaged.

What is known is that all three generations have started with their relationship under wraps, but have been spotted together in public, they have all spoken fondly of their counterparts in interviews, and besides Holland and Zendaya, have all remained good friends after their breakup. Saint Scroll talked with a fellow Spider-Man fan to discuss what she thinks about the relationship pattern and why she thinks Holland and Zendaya went farther than the last two.

Lydia Hong is a sophomore at San Dimas High School, as well as a fan of the Andrew Garfield Spider-Man movies. She says that given the circumstances that the three generations of actors were put through, it was inevitable for emotions to arise during it.

“If you’re forced to be someone’s love interest on a movie set for the entirety of production, I feel like catching feelings for each other isn’t the most outlandish thing in the world.” she says.

She also mentions that the reason for the last two breakups were just normal causes of life.

“It just didn’t work out from what I’ve seen. Plus, from what I know about Tom Holland and Zendaya, he liked her from the very beginning. Sometimes it works out, sometimes it doesn’t, and I guess they just got lucky.”

Maybe the reason for Holland and Zendaya’s success is that they were strong for each other from the beginning. Perhaps the reason for the last two breakups were because of the publicity of it, or maybe they just weren’t right for each other. Whether Garfield had actually cheated on Stone, or if things really did just “fizzle out,” for Maguire and Dunst, let’s rejoice for the new engagement of Tom Holland and Zendaya, a match that was made to be.