Angourie Rice's casting in Spider-Man: Homecoming has led many to speculate that Gwen Stacy could appear again on film, but if she does, the poor girl may have some competition on her hands if she wants another crack at dating Spidey.
As if that wasn't bad enough, Gwen's secret lover was none other than the father of Peter's best friend, Norman Osbourne, who later became the Green Goblin and ended up killing Gwen by throwing her off a bridge. Before she died, Gwen became pregnant with Osborn's twins, who grew up Benjamin Button style to become adults just a few short years later, seeking revenge on Spidey for his involvement in their mother's death.
Honestly, there was more drama in this one story arc than a thousand episodes of Desperate Housewives.
Black Cat is undeniably one of the sexiest vigilantes in comics, putting her own spin on the sultry feline look, but she's also got some surprising kinks that would put Christian Grey to shame.
Felicia dated Peter for quite some time in the comics, but she was only ever interested in his super alter-ego.
Unfortunately, that's what happens sometimes when you date your friendly neighbourhood Spider-Man.
Poor Debra Whitman dated Peter for a short time and at first, things went swimmingly, but after he continued to disappear randomly to save the day, Debra began to suspect that Parker is actually Spider-Man.
These suspicions intensified to the point where Debra was eventually diagnosed with mild schizophrenia and treated for her "delusions".
When Dick Grayson figured out that Bruce Wayne is Batman, he was turned into a kick-ass sidekick.
As soon as the costume came off, Black Cat wasn't interested anymore, presumably leading to some kinky bedroom antics involving masks and a whole lot of spandex.