It's been almost sixty years since Spider-Man first swung into action on the pages of Amazing Fantasy #15. While Spider-Man's comic stories have put out more good content than bad, few series can stretch on for sixty years without making a few missteps along the way. Spider-Man is no exception.

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Spider-Man has had his fair share of mistakes. From deals with the devil to some shocking PSA's, and really rocky relationship choices, the old Parker luck has hit the comics hard over the years. Some choices which seemed daring and bold at the time have lost their luster with age.

10 Spider-Man Fighting For Safe Sex

Spider-Man  shoots webbing into the mouth of Prodigy in a safe sex PSA

Sex education is a touchy subject. It almost always comes off as awkward and unreliable, either in a Sex-Ed class or through "The Talk." In swings Spider-Man to teach teens about safe sex… by fighting a giant-headed pregnancy-obsessed alien?

The Prodigy is a stretch — an evil alien who goes about hypnotizing American youth in order to trick them into pregnancy. He will steal their babies and use them for forced labor on his far-off planet. Is it so hard to build robots that Prodigy would rather steal babies? Maybe the lesson this comic wanted to teach is that a giant head doesn't mean super smarts.

9 One Moment We Want To Forget

Mary Jane discusses  her deal with Mephisto in One Moment In Time.

Everyone makes mistakes. It's just a fact of life. When it happens, what matters is the response. Do they accept it and move on, or double down on their mistake? Spider-Man: One Moment In Time firmly takes the latter option. Like anyone desperately trying to justify a bad decision, it comes off as wonky,

This comic makes some truly strange decisions, particularly around Mary Jane. Her support for Peter and her enthusiasm for her relationship with him was part of what made her special. The idea that she never considered how dating Spider-Man could get her or the people close to her hurt paints Mary Jane as clueless and doesn't do her character justice.

8 Cloning the Clone Saga

Jackal ( Ben Reilly) Resurrects Spider-Man's Villains

Knowing few things are good the second time around, fans were leery when the already bloated Clone Saga was revamped for The Clone Conspiracy. Still, the original Clone Saga created some great characters like Ben Reilly and Kane. Maybe The Clone Conspiracy would make some magic of its own?

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Unfortunately, it was not to be. Ben Reilly, the original fan-favorite Scarlet Spider, was resurrected after his heroic sacrifice. However, he was now the villainous face of the Jackal. To many, this was a betrayal of his character, one that has left the Scarlet Spider stumbling ever since.

7 Performing Baffling Body Swaps

Ultimate Spider Man Hugs Mary Jane after getting his body back from Wolverine

Body swap stories are usually pretty interesting, giving the characters an opportunity to literally walk around in someone else's shoes. They have some arguments, see a new perspective, and learn lessons about being themselves or not taking others for granted. It's a tried and true storyline that's been less than stellar for the web-slinger.

In Marvel's Ultimate Universe, Wolverine once was swapped into Peter's body, and it's implied he tried to sleep with Mary Jane. Not only was MJ unaware Logan was piloting her boyfriend's body, but she was fifteen years old at the time.

6 Gwen Stacy's Double Life

Green Goblin and Norman Osborn in Sins Past

Marvel has been in a Gwen Stacy renaissance lately. From a meta-textual assassin to a spider-themed hero from an alternate universe, it seems she can fit into any role imaginable. As the Sins Past storyline showed, Gwen can't quite fill any role.

One storyline few anticipated nor fondly regarded was when Sins Past revealed Gwen Stacy was in a secret relationship with Norman Osborn, the Green Goblin. The heart wants what it wants, but this is one pairing that should have stayed in fanfiction. It was later retconned into a hypnotic Osborn plot, and many resolved to never speak of it again.

5 A Sinful Smooch

Sarah Stacey Kisses Peter as Mary Jane catches them

Another element of Sin's Past entailed Sarah and Gabriel Stacy. The secret love children of Norman Osborn and Gwen Stacy, Osborn raised them to believe Spider-Man killed their mother and was secretly their father. The two decide to plot their revenge. While Gabriel remained focused on making Peter's life hell, Sarah came to like Spider-man. Maybe a bit too much.

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In the sequel story, Sins Remembered Peter and Sarah head off to France. While there Sarah ends up kissing Peter. Considering she's his old flames' child, that she very recently believed Peter to be her father, and that due to accelerated aging, she can't be older than six, it's easier to count the ways this isn't messed up.

4 The Devil's Own Peter Pan Syndrome

Amazing Spider-Man Peter's deal with Mephisto

Life is all about growing. Even in the super slow pace of comic book time, seeing how characters develop and change is half the fun. Flash Thompson goes from a stock bully to a decent guy to a hero. Harry Osborn goes from best friend to arch-enemy and back again more times than anyone can count.

However, sometimes change can be scary. One thing writers have been scared to do is let Peter grow up. This hesitation led to One More Day, the infamous storyline where Peter Parker sells his marriage to Mephisto. The idea marriage would be so alienating to readers is baffling.

3 This PSA Got A Little Too Real

spider-man and power pack

Comics and PSAs aren't a new combination. When trying to convey difficult information, it helps to have a friendly face. Still, not every PSA was light and fluffy. In one story, Peter overhears a young boy being taken advantage of by his babysitter. Spider-Man intervenes and tells a story of a young boy he used to know, a boy who was shown pornography and then abused by an older teen called Skip.

Yes, this boy turns out to have been Peter himself. While making sure kids know abuse isn't their fault is an incredibly important message, this is a dark turn for a character who's already got a lot on his plate. Is there anything terrible Peter hasn't gone through? Hopefully, the story did some good, but nowadays, it's been mostly forgotten.

2 Siding With the State in Civil War

Spider-Man-Civil-War-reveal

Marvel's Civil War storyline was a great idea, having heroes fight each other over a conflict of ideals with no easy answer. Captain America believes heroes should be free to act according to their own consciences. Tony Stark argues for government oversight. Spider-Man decided to throw in with Tony, even unmasking himself. While both sides have good arguments, the actions taken aren't on equal footing.

From creating a brainwashed clone of Thor to hunting down unregistered heroes, as Tony slipped over to the dark side he dragged Peter's good name down with him. Spider-Man seemed to be either pro-police-state or too naive to recognize what was happening. Spidey ended up switching sides, but in the eyes of many fans, the damage was done.

1 Spider-Man's Power Ended Up Killing His Love

Spider-Man Reign the Spider-Man costume ripping apart.

When Spider-Man's webbing ended up killing Gwen Stacy, it was one of the most iconic and heartbreaking moments in comic history. To this day, every Spidey fan knows "The Night Gwen Stacy Died." It's a tough story to top, but that didn't stop Marvel from trying.

In the Spider-Man: Reign miniseries — Marvel's answer to the Dark Knight Returns — Peter Parker is an elderly widower. It turns out that when Peter was bitten by that radioactive spider, all his bodily fluids became radioactive. After years of intimacy, Peter had slowly poisoned Mary Jane, leading to her death. Of all the ways a character has been killed off, this is by far one of the weirdest.