Summary

• Spider-Man’s dating life has been consistently difficult, with many relationships ending in tragedy or failure.
• Some of Peter Parker’s romantic relationships have left a big impression on readers, both in terms of triumph and mourning.
• Mary-Jane Watson remains one of Spider-Man’s most beloved and enduring love interests, with their romance consistently sizzling off the page.

Out of all the amazing adventures that he’s had over the years, Spider-Man’s most consistent obstacle may arguably be dating life. Dating can be hard for everyone, but it’s proven to be especially hard for someone like Spider-Man, who is as unlucky in love as he can be unlucky in life. Even outside the main Marvel canon of the 616 universe, Peter Parker has had relationships that have gone south, and he has not had the easiest time balancing a love life with his superhero duties. However, for as often as he has floundered on the dating scene, he has also found triumph.

Whether they manage to be brief or long-lasting, there are some relationships that Peter’s had that have not only left a big impression on him but also left an impression on readers enough to have their favorites. In some of these romances, readers triumphed along with Spider-Man to see him progress with the women he’d fallen for, and in others, readers mourned with Spidey as that romance ended in tragedy.

Betty Brant

The First Love Of Peter Parker’s Life

As the saying goes, you never forget your first love, and readers can’t forget Peter Parker’s first canonical girlfriend, Betty Brant. It may be far from Peter’s best or most memorable relationship, compared to those that would flock his way in later years, but she set the stage for the dating life Peter would take part in moving forward. When Peter first started working for The Daily Bugle, Betty quickly took a liking to the young photographer and the feeling was soon mutual the longer Peter took notice of how J. Jonah Jameson’s secretary would stand up to the publisher. A romance soon blossomed, but would soon fall apart when Betty got the impression that Peter’s crush on a classmate – the next entry on this list – would overshadow their own relationship.

Liz Allan

The Classmate that Betty Was Worried About, Understandably So

Although Betty Brant was Peter’s first girlfriend, Liz Allan was his first crush, dating back from the very beginning, making her his first romantic interest in the comics. Peter longed for the popular girl while she was dating popular guy, Flash Thompson, making up the school’s power couple. Peter was merely a nerdy guy who went unnoticed by everyone, so he figured he never had a chance until she started taking an interest in him. To complicate matters even more, she had an even bigger crush on Spider-Man, whom she would ignore both Peter and Flash in favor of. When they graduated, Liz would finally admit to Peter that she had feelings for him, but also acknowledged that they could never be together because life was pulling them in different directions.

Jessica Jones

The Spidey Romance Everyone Forgets

It’s easy to forget or even be completely unaware of the coupling of Jessica Jones and Spider-Man when they’re technically not a couple in the official Earth-616 canon. Granted, it’s worth mentioning that this has roots in the official Marvel canon, as it has been established that before she got her powers, Jessica had a crush on Peter that she never acted on. However, in the reality of Spider-Man: Life Story, while Peter is separated from Mary-Jane, he starts dating Jessica Jones. Their time on-panel is brief, and it isn’t mentioned how their union ends – just that they start dating in 1995, and by 2019, she’s one of the heroes who are either dead or missing after Doctor Doom assumes worldwide political power. In their brief time together, their chemistry is off the charts and, of course, a relationship between two heroes of this magnitude is hard to forget.

Captain Marvel

A Power Couple That Needed More Time

Speaking of relationships between two heroes of large magnitudes, the same can be said for Peter’s time dating Carol Danvers during her tenure as Ms. Marvel. Their relationship was just as brief as the previous entry, but the difference is this happens in actual Marvel canon. It all starts in Ms. Marvel #34 by Brian Reed, Paulo Siqueira, and Adriana da Silva Melo. Spidey accidentally asks Carol on a date if he can help her during a time when she’s de-powered. A woman of her word, she agrees and the dinner date in question is awkward, to say the least. Although the date ends well, it seems like the chemistry isn’t strong enough to warrant anything serious. However, during the Siege event when Venom infects Carol, the symbiote mentions Carol has feelings for Peter. The would-be couple talk about it, but it’s never followed up on story-wise. It’s a shame this couple was never given more time to blossom and develop.

Silk

Two Heroes Bitten By The Same Spider Can’t Keep Their Hands Off Each Other

Out of all of Peter’s relationships, this one, hands down, has to be Spider-Man’s most sexually-charged romance. Peter Parker and Cindy Moon bond over the fact they were both unknowingly bitten by the same radioactive spider. Their shared Spider-Sense is strong enough that whenever the two are in close proximity to each other, they get a sudden urge to pounce on one another. To say that the spider pheromones make superhero team-ups with each other difficult would be an understatement. It’s one of the reasons why Silk opts to venture out on her solo adventures, but the fact that she’s in a position to successfully carry her own series speaks to the popularity she gains from offering Peter his most unique romantic dynamic.

Kitty Pryde

The Ultimate Partner For Spider-Man

This pairing was exclusive to the Ultimate Universe, but it’s one that many readers view as Spider-Man’s best love story in the comics, one that might warrant his entry into the X-Men. During this time, Kitty and Peter are frequently featured alongside Iceman and MJ, respectively, but when both parties break up, Kitty and Peter decide to act on a long-time crush. The two not only become romantic partners, but superhero partners. Kitty even goes out of her way to create a brand-new secret identity for herself, to make it less obvious that Peter and Spider-Man are the same whenever she is seen in public with him. The pairing is what happens when two witty, often snarky, and charming personalities naturally come together.

Carlie Cooper

Arguably Spider-Man’s Most Underrated Romance

Becoming romantically involved with Peter not long after the One More Day fiasco, it’s easy for fans to forget and maybe even dislike Carlie Cooper when there was so much controversy surrounding Spider-Man right before she was even introduced. Carlie easily could have been overshadowed by that controversy, and in many ways maybe she was. However, those who do remember Carlie remember the NYPD forensic scientists fondly. She dates Peter not long after debuting but breaks up with him after learning he’s Spider-Man, understanding the danger that comes with it (which, for a normal citizen, is pretty smart). The two remain good friends afterward, and she manages to be a helpful ally in his superhero pursuits as well. Sadly, as most love interests of Spider-Man tend to end up, his run with Carlie Cooper ends in tragedy when she’s captured by the Green Goblin, who injects her with Goblin Formula, turning her into the creature known as Monster.

Black Cat

The Femme Fatale Of The Marvel Universe

The femme fatale who plays both foil and occasional lover to the protagonist continues to be an enduring trope in the comic book industry. Many pinpoint how DC utilized Catwoman as a reason for this, but those same people can’t overlook the impact of Marvel’s Black Cat (who, surprisingly, was not even inspired by Catwoman). While not every reader will point to Black Cat as their favorite Spidey romance, it’s hard to argue against Black Cat at least being Spider-Man’s most fun relationship. It’s as entertaining as it is complex to see Spider-Man smitten with someone he has to apprehend as a cat burglar, and vice versa. Black Cat’s resurgence as a redeemed hero has offered her continued longevity, but her love affair with Spider-Man remains as captivating as ever.

Gwen Stacy

Spidey’s Doomed Love Is Rightfully Mourned

There once was a time when Gwen Stacy was portrayed as Spider-Man’s one true love. While that wasn’t quite the case, that doesn’t change the fact that both her life and death left an immense impact on Peter’s life. The more time passes since Gwen’s death, the harder it gets not to mention Gwen when talking about anything Spider-Man-related. Even as recently as 2022’s Amazing Spider-Man #10, writers try to find new ways to incorporate Gwen into new storylines, be it literal or indirect mentions. Every decision that Spider-Man makes is largely influenced by what happened in “The Night Gwen Stacy Died.” It’s not just because she was someone who died tragically on his watch, but because he loved her so much that he refuses to forget how hard it hurt for him to lose her.

Mary-Jane Watson

Pete’s Most Famous Lover, And With Good Reason

From the moment that Mary-Jane Watson first utters her iconic line, “Face it Tiger, you just hit the jackpot!” upon her introduction in Amazing Spider-Man #43, readers were certain that Peter really hit the jackpot. When Gwen Stacy died, MJ had big shoes to fill given how prominent and beloved Gwen was at the time, but miraculously, MJ’s presence and impact on Peter’s life has been just as endearing to the public as Gwen Stacy was, if not more. There’s a reason why there remains such a venomous outcry from fans begging for MJ and Peter to get back together. In nearly 60 years of existing, MJ remains an exciting, multi-faceted presence in Spider-Man’s life as their romance always consistently sizzled off the page.