As anticipation builds for Spider-Man: Brand New Day, fans are revisiting the web-slinger’s unforgettable journey on the big screen, including the romances that have defined each era. While Peter Parker has faced countless villains, his love life has remained just as memorable, with different actresses bringing unique interpretations of his iconic partners. From Kirsten Dunst’s beloved portrayal of Mary Jane Watson in Sam Raimi’s trilogy to Emma Stone’s Gwen Stacy and Zendaya’s Michelle ‘MJ’ Jones-Watson in the Marvel Cinematic Universe, each character has left a lasting mark on Spider-Man’s story.