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Spider-Man, also known as Peter Parker, has experienced the loss of his love interest multiple times in various comic book storylines and adaptations. One of the most iconic instances is the death of Gwen Stacy. In "The Amazing Spider-Man" #121 (1973), Gwen Stacy, Peter's girlfriend, is tragically killed by the Green Goblin. This event had a profound impact on Spider-Man, shaping his character and future relationships. The loss of Gwen Stacy is a significant moment in Spider-Man's history and is often remembered as one of his most heartbreaking losses.