Spider-Man has been winning hearts since his first appearance in Amazing Fantasy #15 (1962), those of fans and apparently those of most women in the Marvel Universe as well. Although Mary Jane is usually considered to be his main squeeze, this is one guy that has played the field and left it covered in broken hearts.
For someone that constantly bemoans his supposedly catastrophically bad luck, Peter Parker sure does 1) have rad superpowers, 2) cause almost all of his own problems, and 3) date an unusually high number of incredibly beautiful and amazing women. Even Mary Jane told him point blank that he’d hit the jackpot, Tiger, but still, he could not see his own amazing fortune. We can, though, and we’ve been taking notes. Besides the usual suspects of Gwen Stacy, Mary Jane Watson, Betty Brant, and Miss Felicia Hardy, here’s another handful of times when Peter Parker was lucky in love.
The Clone Saga is known for many things, but “being good” isn’t one of them. Running for right around two years and featuring what Wikipedia refers to as “many clones,” this is a real sore spot for a lot of Spider-Man fans. The story featured a paradoxically (or peroxide-ically) blonde Peter Parker clone named Ben Reilly who took over for Spider-Man when Peter Parker finally decided that he was absolutely over it. While The Clone Saga eventually ran its course, the story had repercussions for years, and it took a good long time for the many running Spider-Man series of the time to get back on track.
Next: the man that murdered Peter Parker’s Uncle Ben is known as “The Burglar” because comics of the 1960s were not huge on humanizing their villains. In other media, he has been named Dennis Carradine, with the last name coming from his daughter Jessica’s appearances during the Clone Saga. He has also been referred to by the descriptive titles “The Carjacker” and “Cash Register Thief.” Let’s face it if your parents name you Cash Register Thief, your life is going to go a certain kind of way.
Jessica showed up on the scene pulling a real Peter Parker and trying to get quality shots of Spider-Man, yet another once highly coveted job that millennials are killing. She is convinced that her father was a decent guy who Spider-Man framed and killed, and her very brief attraction to Reilly ends when she discovers he is Spider-Man, which is the only logical outcome for this incredibly convoluted soap opera of a situation. Listen, I’m not here to tell people how to live, but it is possible that dating the child of the man that murdered the uncle of the man from which you are cloned isn’t a great idea. Maybe I’m just being paranoid, but it seems like it could arouse some pretty conflicting emotions for, I don’t know, literally every person involved. On the other hand, it does prove one of my longest running theories, which is that Peter Parker and all clones thereof are messy nerds that live for drama.
When Peter Parker talks about being unlucky, he probably actually means that it’s really unlucky to develop a crush on him, and nowhere is that more glaringly, shockingly true than it is for one Ms. Debra Whitman. She and Parker met via her job as a secretary at Empire State University, and their brief flirtation led to a few dates that he completely, 100% bailed on because he actually is a schmuck.
Whitman ended up in an abusive relationship and her mental health deteriorated after her strong suspicion that Peter Parker actually was Spider-Man was disregarded as hallucinations by her therapist as well as by pretty much the entire rest of the world, including her temporary boyfriend Biff. Parker eventually confessed that he was indeed Spider-Man, but only after many issues of everyone treating her like she was unstable and hysterical for daring to believe that Parker was a superhero. Fair enough, altruism on Parker's part does seem increasingly unlikely the longer this entry goes on.
Let it be known that any man that pushes you so far over the edge that you date a guy named Biff to rebound is not ever going to treat you right and it’s for the best you forget all about it no matter how many sad eyebrows he makes at you. Besides all that, Debra eventually ended up writing a book literally called How Spider-Man Ruined My Life after he revealed his true identity to the world during Civil War and threw her for yet another loop. She eventually recanted her story, but it doesn't even matter. Later Mephisto erased her knowledge of Spider-Man’s true identity because apparently this lady was born to have people mess with her head.
We all know that there is pretty much no way that Peter Parker has anything to offer the highly sought-after spy extraordinaire Natasha Romanov, but then again Natasha has been known to expand her horizons when in a pinch. In Marvel Team-Up #82, Spider-Man had a very brief flirtation with Black Widow due to the fact that she completely forgot she was Black Widow and instead believed herself to be a school teacher named Nancy Rushman. Yes! It is Marvel and it is the ‘70s.
Nancy Rushman is just wandering around NYC like you apparently do and naturally she gets robbed because that is what happens every time any person wanders around any city in a comic. Spider-Man sees her and jumps in to save the day at which time Natasha karate chops the criminals and drops them, then shrugs it off like that’s a normal thing for a school teacher to do. Spider-Man recognizes her and insists on helping her recall her past identity, which is cool but also it means that she goes from being super into him to remembering that she’s literally Black Widow and can have any man along with a huge swath of the world’s female and genderqueer population that she could ever want. Sorry, Spidey.
This story is pretty cool because it ends with Natasha just kind of saying, “it ain’t me, babe” and bouncing on Parker. This is definitely for the best, considering the fact that his relationships all go catastrophically wrong if they last longer than one single issue. This story is one single issue, but Spider-Man is not, and it’s best for everyone that Natasha moseyed on out of his life.
The X-Men aren’t particularly known for having much in the way of storyline coherence, and Marrow is one of their many characters who has been absolutely all over the place since her inception. Sarah began as a young Morlock who was sent to a pocket dimension then returned to standard Marvel continuity just to be a jerk to the X-Men for pretty much no reason. After that, Marrow had her heart ripped out by Storm and it was awesome.
What? It was awesome.
She lived, though, because it is impossible to die in a Marvel comic, even if you try really hard. Marrow, who was marked by having a particularly unattractive power set in which bones would rapidly grow from random places on her body, was made beautiful by Gambit somehow and therefore became much nicer, because all women really want is for men to think that they’re pretty and if they get that then they’ll be happy and nice to Gambit despite having no reason to be nice to Gambit. That's just basic science.
Unfortunately, even though she was pretty and therefore a good person, she was still a character in the Marvel Universe and thus doomed to perpetual tragedy. She was brainwashed by S.H.I.E.L.D. for whatever random S.H.I.E.L.D. reason, but, even worse, that’s when Peter Parker took an interest in her. As if this girl needed any more problems in life. The relationship ended when she regained her memories, and her whole personality changed once more by the next time we see her because this character is written incredibly inconsistently and probably always will be. Anyway, Spider-Man got with her for a little while.
The Marvel Adventures: Spider-Man series was a youth-oriented book meant to be relatively uncomplicated takes on the Marvel Universe. As we all know by now, “relatively uncomplicated take on the Marvel Universe” generally just ends up even further complicating continuity (see: the Ultimate universe) but the Marvel Adventures stories did a better job of offering a clean alternative to the very messy world of Marvel than usual. Late in the first run, Emma Frost showed up at school with her best friend Chat. Although their relationship is tumultuous, it's kind of a huge relief to see Emma Frost finally have a female friendship in at least one continuity.
Emma was the strident, brassy friend while Chat was the mousy, shy friend, and, as we all know, that is a match made in trope Heaven. They got along really well until a wedge grew between them due to Emma’s immediate acknowledgment of Peter Parker’s secret identity and her willingness to weaponize Chat’s crush on Parker against her.
I love Emma, so I want to say this is out of character for her, but I love Emma, so I know just as well as everyone reading this that it’s actually incredibly in character for her despite taking place in an alternate reality. In the end, Emma did the right thing and backed off, and Chat and Peter started a brief, out-of-continuity relationship while Emma went on to happily ruin lives elsewhere. What can I say, the girl’s got an M.O.