Peter Parker/Spider-Man has had about a dozen love interests throughout his nearly 60-year-long existence, but two stand head and shoulders above the rest for iconic status: Mary Jane Watson and Gwen Stacy. MJ has been Peter's most consistent love interest, both on comic page and TV screens, while Peter's failure to save Gwen's life has haunted him since.
Both of these two special women in Peter Parker's life have numerous stories chronicling their relationship with the Web-Slinger, so let's narrow these tales down to the Top 5 of each.
10 Gwen: Amazing Spider-Man #47-49
Gwen may have been formally introduced in The Amazing Spider-Man #31, but it was only some 15 issues afterwards that her most familiar personality, the innocent, bubbly blonde infatuated with Peter Parker, emerged. On the surface, this 3-issue collection has some by-the-numbers superhero storytelling, featuring Spider-Man facing off with Kraven and The Vulture, but what makes this story stand out is that it's a critical junction in Spider-Man's love life.
Seeing MJ on-and-off but finally noticing Gwen the way she notices him, Peter's forced to choose between the two of them; in a decision that sets the status quo for the next seventy or so issues, he chooses Gwen.
9 MJ: "To Have & To Hold"
This Matt Fraction-penned one-shot, told in Sensational Spider-Man Annual #1, was one of the final stories focusing on Peter & MJ before the reviled One More Day retconned their marriage from history. But hey, at least they went out on a high note. With Peter on the run after Civil War, MJ is ambushed by a federal agent, offering her immunity if she rats out her husband, while Peter attempts to surreptitiously turn himself in to the NYPD, hoping to buy immunity for his wife.
From there, the story flips between past and present, offering some Rashomon-esque flourishes as readers see moments in Peter and MJ's relationship play out from their individual perspective. While the denouement of Peter declaring "You and me, now and forever" rings bittersweet given subsequent stories, "To Have And To Hold" still stacks up on its own merits.
8 Gwen: Spidey
The 12-issue Spidey series ran parallel to the main Spider-Man titles, telling the story of the Peter Parker of a parallel Earth who was still in High School, whereas the main Spider-Man of Earth-616 had long since graduated. Interwoven between stories of Peter's early adventures as Spider-Man is his burgeoning relationship with Gwen.
While the original Peter & Gwen may not have met until their college years, Gwen being the generally accepted choice for Peter's "first love" made her a natural inclusion in this rewrite. The two's attraction grows closer throughout the series, from Peter tutoring Gwen to the two bonding over shared interests such as Lord Of The Rings, culminating in the final issue, where they attend a homecoming dance together and share a kiss.
7 MJ: "The Wedding"
While they had been on-and-off for almost fifteen years by the time this story was published, The Wedding, published in The Amazing Spider-Man Annual #21, is what cemented Mary Jane as the one-and-only girl for Peter Parker.
After rejecting his proposal twice, MJ finally accepted in Amazing Spider-Man #292. despite doubts on both their ends, from Peter's lingering guilt over Gwen's death to MJ's hesitance about settling down, the wedding goes through without incident, and the newly-weds prepare to live happily ever after (and they do, for 18 years anyway).
6 Gwen: Spectacular Spider-Man
If Gwen's resurgence in popularity over the past decade can be traced back to one incarnation of Spider-Man, its the sadly short-lived cartoon Spectacular Spider-Man. After being ignored in past Spider-Man cartoons in favor of MJ and only receiving a minor supporting role in the final chapter of the Raimi trilogy, Spectacular's Gwen was put front-and-center as Peter's primary love interest.
Though introduced as mere friends, with Peter oblivious to Gwen's interest, he gradually begins to recognize his own feelings for her, and while the series' cancellation prevented them from ever officiating a relationship, its clear that moment would have come sooner or later.
5 MJ: "Parallel Lives"
Amazing Spider-Man #256 revealed that MJ had discovered Peter's secret identity long ago, but kept her knowledge a secret from everyone, Peter included. Gerry Conway's Parallel Lives revealed the exact circumstances of how MJ discovered Peter's secret, and shows how the couple were truly made for each other.
After an opening chronicling the pair's early years, switching focus from Peter to MJ before the two meet, the story reaches present day, where a battle with Doc Ock almost prompts the eternally guilty Peter to end his relationship with MJ, before she swiftly convinces him otherwise.
4 Gwen: "Spider-Man: House Of M"
Gwen's murder, especially his failure to prevent it, has haunted Peter every moment of his life since, so it's no surprise that, when the Scarlet Witch altered reality to give everyone their greatest desire, history is rewritten so that Peter saved her on that fateful night.
From there, the relationship continued to blossom, until eventually the two married and had a son together. Tragically, the restoration of the original reality necessitates that Peter must lose Gwen again, and having to say goodbye to his love and their son nearly breaks Peter.
3 MJ: "Confessions"
The Ultimate incarnations of Peter and MJ have many differences from their classic counterparts, but one thing that didn't change was their love for each other.
In Ultimate Spider-Man #13, "Confessions," one of the main status-quo switch-ups was introduced when Peter revealed his secret identity to MJ, making her the first person he (willingly) shared his secret with. From this story onward, MJ became not just his girlfriend but also his confidante, the only person in his life who he could talk to with complete honesty.
2 Gwen: Spider-Man Blue
Part of Jeph Loeb & Tim Sale's "Marvel Colors" anthology, featuring heroes reminiscing about lost loved ones, Spider-Man Blue retells the early days of Peter's relationship with Gwen. The series employs a framing device of Peter, many Valentine's Days after Gwen's last one, recording tapes recounting their relationship and describing his love for her, hoping she may hear them in whatever place she's in now.
Though repeatedly dogged by super-villains and trapped in a love triangle, Gwen ultimately wins Peter's affections, though their first kiss is a bittersweet moment since we know the tragedy that will follow.
1 MJ: Spider-Man Blue
Spider-Man Blue may fundamentally be a story of Peter and Gwen's romance, but as Peter himself puts it, "You can't really tell the story of how Gwen Stacy and I fell in love without talking about Mary Jane Watson."
The series recreates MJ's first meeting with Peter, as she competes with Gwen for his affections throughout the series. In the final issue, MJ appears in the story's present day; in a touching moment, after she discovers Peter making the tapes for Gwen, she only asks her husband to tell Gwen that she misses her too.