From Mary Jane to Gwen Stacy and Michelle ‘MJ’ Jones, Peter Parker’s web of lovers has spanned comics, films, and series.

Tobey Maguire: Spider-Man trilogy (2002–2007)|

Mary Jane Watson (Kirsten Dunst) is the axis of Peter’s early life, although fans have debated her character as being manipulative and strategic, often pursuing the most desirable men in the room and wielding her charm to shape social outcomes. First glimpsed moving in next door during Spider-Man (2002), Mary Jane embodies vivacity and ambition, a foil to Peter’s shyness. Their relationship begins in unrequited tension—she dates Flash Thompson, Peter’s high-school tormentor, yet every act of heroism deepens their connection. The defining moment arrives in the film’s iconic upside-down kiss, where Maguire’s Peter protects Mary Jane from the Green Goblin, crystallising love and duty into a single image. Across the trilogy, Mary Jane’s pursuit of an acting career in New York juxtaposes Peter’s secret life, creating distance, misunderstanding, and dramatic tension, particularly in Spider-Man 2 (2004) and Spider-Man 3 (2007). Even as Peter flirts recklessly under the symbiote’s influence and she becomes briefly engaged to John Jameson, Mary Jane remains his emotional anchor—the constant that grounds his heroism.

Betty Brant (Elizabeth Banks) first appears at the Daily Bugle, working as J. Jonah Jameson’s secretary. Peter notices her across the bustling newsroom, often reacting shyly to her subtle flirtations—a tilt of the head, a quick smile, a teasing comment about his photo assignments—while she clearly shows more interest than he initially acts on.