There's a good reason that several people of varying ages and generations latch onto Spider-Man. It often is harder to like your heroes when they fail, but there is just something about Peter Parker that makes his failures gripping, mostly down to the sheer emotion that comes when he wins.
Boiled down to his core, Peter is just a regular guy, so when he experiences a heartbreaking moment, it really hurts. With that being said, it also means fans can get all the more mad at him when he is the one to blame for the problems in his life.
Felt Bad: Accidentally Killing Wolverine's Lover
Jim Owsley (later known as Christopher Priest) delivered a truly dark noir in the form of Spider-Man Vs. Wolverine. Analyzing the disparity between Peter and Logan in a way that feels really uncomfortable in certain areas, especially in the tragic finale.
Ending with Spider-Man accidentally killing Charlemagne, Wolverine's doomed lover, by punching her when he thought she was Wolverine, Spider-Man is forced to do something he wouldn't normally do, even though she wanted to die. What hurts more is that in the aftermath, Spider-Man is so haunted by the moment that he remembers it at random moments.
Hated Him: When He Was Mockingbird's Deadbeat Boyfriend
Dan Slott is a phenomenal writer, bring us several great stories in the pages of Amazing Spider-Man, but Peter's relationship with Bobbi Morse/ Mockingbird was a real low point in his run. After the fall of Parker Industries, Peter slept on Bobbi's couch, becoming kind of a loser.
Mockingbird is an interesting figure in Peter's romantic history, as she's the first superhero he's been with in a romantic capacity, but they'd be the first to admit they have nothing in common. At least fans got an awesome panel of Peter wearing Bobbi's "Ask Me About My Feminist Agenda" shirt out of this.
Felt Bad: Being Hounded By J. Jonah Jameson
J. Jonah Jameson is one of Spider-Man's greatest foes, doing more damage to him than most of his villains combined. For years, Jameson had an irrational hatred for the Web-Head and would take any opportunity to twist people's perception of him.
However, this one thankfully has a happy ending thanks to Chip Zdarsky, as when Jameson was at his lowest point, Spider-Man agreed to do an interview with him. After Jameson bared his soul to him, Peter revealed his identity to his former boss and has had an ally in Jameson since.
Hated Him: Never Telling Aunt May The Truth
Peter Parker's relationship with Aunt May is one of the key elements of who he is, but he has been somewhat irresponsible in this regard. Not only would Peter occasionally use May as a scapegoat, but he'd also go to ludicrous lengths to avoid her finding out he's Spider-Man so that she wouldn't "worry about him."
Peter's attempts to weave around telling Aunt May the truth would come back to bite him in the rear when J. Michael Straczynski took over. After Peter was injured in a battle with Morlun, May found his battered suit and later confronted him with it, truly shaking up Spidey's status quo.
Felt Bad: When Doc Ock Stole His Life
Along with Green Goblin, Doctor Octopus is one of Spider-Man's greatest physical threats, but their opinions of each other were rocked forever in Dan Slott's Superior Spider-Man. When Peter dies in Doc Ock's body after a body swap, Otto Octavius vows to live up to Peter's legacy.
The problem is Peter's consciousness is forced to follow Otto around, watching in horror as the "Superior" Spider-Man did some truly questionable things. The nadir came when poor Peter was forced to watch as Otto seduced his ex-wife Mary Jane Watson.
Hated Him: When He Hit Mary Jane
Domestic violence is a big turn off for just about everyone, so seeing our heroes commit such horrific acts is truly sickening. Fans are still pulling their hair out over Hank Pym hitting The Wasp for understandable reasons, but does anyone remember when Peter did the same thing to Mary Jane?
In the heat of "The Clone Saga," writer Tom DeFalco had Peter attack his clone Ben Reilly for stealing his life and when Mary Jane tried to intervene, Peter hit her. While he was horrified by what he just did, that doesn't make up for it whatsoever.
Felt Bad: Being Buried Alive By Kraven
While the incident during "The Clone Saga" was a notable blemish, Peter and Mary Jane's love for each other is cherished by many fans, with "Kraven's Last Hunt" seeing their love save Peter's life. In J.M. Dematteis' acclaimed story, Peter is shot and buried alive by an increasingly unhinged Kraven The Hunter.
As Kraven masquerades as a more violent Spider-Man, Peter tries to burrow his way out of his own grave, with his love for Mary Jane being the thing that keeps him going. This is Spider-Man defined, no matter how overwhelming the obstacle, he will use the people in his life as motivation to overcome his trials.
Hated Him: Selling His Marriage To Mephisto
Fans will likely stop hating on "One More Day" when the heat death of the universe occurs. A story forced upon J. Michael Straczynski by Joe Quesada, Peter Parker selling his marriage with Mary Jane to Mephisto is one of the worst choices he has ever made.
Mary Jane didn't look that great in this scene either, as she also agrees to sell the marriage to save Aunt May, who'd probably rather die than have them sell their soul to a Satan cosplayer. Still, this is Peter at his lowest.
Felt Bad: Gwen Stacy's Death
Of all of Peter's greatest losses, Gwen Stacy's murder at the hands of The Green Goblin will forever be the most brutal. Written by Gerry Conway, "The Night Gwen Stacy Died" is one of the greatest tragedies in comic book history.
Gwen wasn't a deep character by any means, but it still hurt when her life was snuffed out by a petty businessman who wouldn't last much longer himself. Though it helped get Peter together with Mary Jane, this was still a moment where fans really felt bad for Spidey.
Hated Him: Being Responsible For Uncle Ben's Murder
Amazing Fantasy #15 did a lot to establish how Spider-Man was going to be different from the likes of The Fantastic Four and Superman. Portraying him as selfish and bitter, the comic depicts Peter's more arrogant move when he allows a robber to get away instead of stopping him.
This selfish move costs Peter Uncle Ben, who'd been a surrogate father for him. Though the famous quote about power and responsibility is often falsely attributed to Uncle Ben, the mix of his demise and such a harsh moral lesson would shape Peter into the hero he would become.