Kirsten Dunst and Tobey Maguire
The original Peter Parker and Mary Jane Watson's chemistry was clear from the beginning, just remember that kiss! Yes, the upside-down in the pouring rain kiss. Iconic.
Though the Kirsten and Tobey kept the details of their relationship private, director Sam Raimi revealed to the Sydney Morning Herald in 2007 that the couple dated briefly while filming the first installment of his Spider-Man trilogy. After their breakup, Raimi explained, "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. And that relationship probably just added to their ability to trust each other."
Kirsten and Tobey's relationship also caught the attention of co-star James Franco, who played Harry Osborn in the movies, Mary Jane's other love interest and Peter's best friend. In an interview with Playboy in 2013, he revealed that the love triangle existed off set, too. "I had a crush on Kirsten, and I think I was upset about that as well," he said.
Luckily, everyone involved was able to maintain a sense of professionalism moving forward, and the sequels were box-office hits. In more recent times, Kirsten has remembered her Spider-Man experience fondly, telling Marie Claire UK in 2017, "We made the best ones, so who cares [about the Spider-Man reboots]?"