When somebody says Spider-Man and romance, most people (even those who don't read the comics) will think of one of the two following couples: Peter Parker and Mary Jane Watson or Peter Parker and Gwen Stacy. Both of these couples are the most iconic ones in Spider-Man lore. However, it would be a mistake to presume they're the only ones.
While the Spider-Man films have yet to show the audience many different couples outside of those two, the comics are a different story. But not all of the relationships in the comics sat well with the readers. And some of them, while they were well-accepted, still ended up being strange for a multitude of reasons.
Gwen Stacy And Norman Osborn
By far one of the weirdest romances happened between Norman Osborn and Gwen Stacy. It was a controversial point in the comics and many fans didn't take it well. And it's not just because Norman was old enough to be Gwen's father.
Gwen Stacy also wasn't previously portrayed as the type of girl who would cheat on Peter. To make matters even more complicated, she got pregnant and gave birth to twins. That didn't stop Norman from murdering Gwen later because he knew it would hurt Peter. This story was twisted from the start.
Ultimate Spider-Man And Black Cat
In the Ultimate Spider-Man series by Brian Michael Bendis, Peter is still a kid. Black Cat, his enemy and occasional love interest in the comics, is a few years older than him. The age difference between them makes the fact that Black Cat keeps flirting with Spider-Man awkward.
To be fair to Black Cat, she has no idea how young Spider-Man is underneath his mask. Also, when she finally finds out, she immediately stops their relationship but the whole thing still felt odd.
Spider-Man And Deadpool
This isn't a traditional romance since it's one-sided. Deadpool flirts with Spider-Man and overall acts like he has a crush on him but Spider-Man isn't interested in Deadpool that way. In fact, Deadpool irritates Spider-Man more often than not.
They form a tentative friendship in the end but even though many fans might wish it would change, Spider-Man and Deadpool don't seem like they'll be dating any time soon.
Spider-Man And Captain Marvel
This couple might seem even stranger to those people who compare it with the MCU. In the MCU, of course, Carol is much older than Peter, having been born in 1966 and 2001, respectively.
However, they had a brief romantic relationship in the comics when Carol was still using the Ms. Marvel moniker. This storyline didn't last long, though, and it had no big impact on the comics, unlike Peter's other relationships.
Spider-Man And Black Widow
Peter Parker has a soft spot for redheads - at least in the comics. But even though Black Widow is his type, this romance was just plain weird. Black Widow wasn't herself when she fell for Spider-Man.
Hydra had altered her mind and Natasha believed she was one of her aliases, a woman named Nancy Rushman. Once Natasha came back to her normal self, any feelings she had for Spider-Man vanished.
Spider-Man And Jill Stacy
In the MCU, Captain America had no objections against kissing Peggy Carter's niece Sharon Carter shortly after Peggy's death. Luckily, the relationship didn't go anywhere. Something similar happened with Peter Parker and Gwen Stacy's cousin Jill when she was determined to find out what happened to Gwen.
She met Peter and made a pass at him but stepped back when she learned about his relationship with Mary Jane. And it's a good thing she did because the notion of Peter dating his first love's cousin doesn't feel right.
Aunt May And Doctor Octopus
Peter's Aunt May is closely connected to his uncle Ben. But she multiple romantic interests in the comics, including the Avengers's butler Jarvis. However, one of her weirdest relationships was with Doctor Octopus, the iconic Spider-Man villain.
This couple went as far as to get engaged. The reason why Doctor Octopus was interested in May was that she inherited an island where a nuclear plant was - and Doctor Octopus wanted the plant for himself!
Spider-Man And Betty Brant
Both in the comics and in the MCU, Betty Brant got together with Ned Leeds. However, she was Peter's first girlfriend in the comics. They worked together at the Daily Bugle under J. Jonah Jameson's leadership.
The main problem with the relationship was that Betty didn't know Peter was Spider-Man - and she blamed Spider-Man for the death of her brother. Needless to say, it didn't end well.
Spider-Man And Anna Maria Marconi
As seen with Black Widow and Spider-Man, it's never a good idea to form a romantic relationship when one of the partners isn't themselves. That was also the case with Spider-Man and Anna Maria Marconi. Doctor Octopus took over Peter's body and he started dating Anna.
He even considered proposing to her. They weren't a bad couple and Peter and Anna stayed friends even after Peter got control over his body back.
Spider-Man And Marrow
Finally, there's the curious case of Spider-Man and Marrow. At the time of their relationship, Marrow was also brainwashed and believed herself to be Sarah Rushman (another false name Black Widow sometimes used).
Marrow pretended to be a student at the Empire State University in order to destroy the life-model decoys. When Marrow came back to her normal self and discovered Peter's secret identity, their relationship was over.