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Tobey Maguire and Kirsten Dunst in Spider-Man
Spidey's romance senses first started tingling in 2001, when Tobey Maguire starred as the web slinger in the first modern, live-action Spider-Man movie.
Kirsten Dunst was cast as Mary Jane, the girlfriend of Spider-Man's alter-ego, Peter Parker -- and it didn't take long for their romance to swing offscreen.
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The duo remained so tight-lipped about the relationship that even the film's director, Sam Raimi, said he didn't realize his two stars were romantically involved until after their breakup -- which they also did quietly.
"I actually had some worries about [their breakup]," Raimi, who directed the pair in all three of the original Spider-Man films, told The Sydney Morning-Herald in 2007 after Spider-Man 3 was released.
"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," he added. "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."
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While Maguire and Dunst never gave many details, their costar James Franco revealed his feelings on the relationship in a 2013 interview with Playboy.
"Tobey and Kirsten became a couple around that time," he said. "I had a crush on Kirsten, and I think I was upset about that as well ... Tobey was mad at me for a while. By the second film, we were cool."
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Andrew Garfield and Emma Stone in The Amazing Spider-Man
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Garfield and Stone's relationship outlasted the franchise, and the couple ended up staying together for four years, until their split in 2015.
PEOPLE broke the news, with a source saying that they had ended things a few months earlier. “There was no drama, they’ve been apart while working. They still care about each other," the source said at the time.
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The duo remained friends after their amicable split, and when Stone won a Golden Globe for her performance in La La Land earlier this year, Garfield was seen giving her a standing ovation.
“We care about each other so much, and that’s a given, that’s kind of this unconditional thing,” he said on Little Gold Men podcast in January.
Stone hasn’t been tight-lipped about her admiration for Garfield since their split, either. In an October interview with Vogue, she said Garfield is “someone I still love very much.”
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Tom Holland and Zendaya in Spider-Man: Homecoming
“They started seeing each other while they were filming Spider-Man,” a source told PEOPLE on Thursday. “They’ve been super careful to keep it private and out of the public eye but they’ve gone on vacations with each other and try and spend as much time as possible with one another.”
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Holland made his West End debut in the title role of Billy Elliot the Musical in 2008, while Zendaya is known for starring in Disney Channel’s K.C. Undercover.
“They’re both really ambitious and they challenge each other — but, most importantly, they make each other crack up," said an insider. "They seem to have a really similar sense of humor and love joking around together. They have great banter back and forth.”
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Shortly before the July 7 premiere of their film, Holland, 21, opened up to PEOPLE about how Zendaya, 20, has helped him navigate the spotlight.
“We are like the best of friends. She’s so great and amazing,” Holland said of his costar. “I’m a little worried [about dealing with fame … but] Zendaya is super famous and she’s been through this and I just call her up and say, ‘How do I manage being famous?’ I’m very glad I have a friend like her.”
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