10 Times Spider-Man Was A Real Jerk
8. Sold His Marriage - One More Day
This classic jerk move on the part of the webhead is further down the list because circumstances had him up against the wall and he WAS trying to do the right thing - or at least some amalgamation thereof - when it happened, but it's still pretty cringe.
When the revealing of his secret identity leads to his aunt being shot by the Kingpin's henchmen, Mephisto confronts Peter with an offer to save Aunt May with a very simple price in exchange: his marriage to Mary Jane. Why he wants something as specific as their marriage is beyond me, but hey, I'm not the devil.
Peter, given the choice between a future with Mary Jane or a future with the old woman who has been dying basically since she was introduced, chooses to erase his marriage to MJ.
Good intentions aside, doing this was not just blatant editorial mandate from Marvel, but in universe - ungodly short sighted on Peter's part.