1. Eating his wife alive (marvel zombies) 2. Killing himself after ruining thousands of human lives(House of M) 3. Seeing the city he lived to protect be destroyed around him(Ultimatum) 4. Selling his marriage to devil to save the life of a woman who repeatedly told him she didn't want to live anymore(one more day) 5. Finding out the girlfriend who died in his arms halfway through his career, giving him buttloads of trauma, had cheated on him with his archnemesis(the one who killed her) and spawned demonic children 6. Being replaced for a day by the chameleon who ruined his relation with a lot of people 7. He still doesn't know whether he is peter parker or a clone with false memories
