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During a time-hopping quest with Wolverine, Spider-Man fell deeply in love with Sara Bailey and almost proposed to her before everything fell apart.
Peter Parker’s love life has often been defined by grief and loss. His first love, Gwen Stacy, was killed by his nemesis during a battle. His other primary love interests, like Mary-Jane, Black Cat, Carlie Cooper, and others have gone through their own torments due to their connection to the Wall-Crawler. But one of the most surprising romances Spider-Man ever had was also one of the most serious, and it almost ended with the hero married.
In Astonishing Spider-Man & Wolverine (by Jason Aaron and Adam Kubert), Peter Parker met and fell in love with Sara Bailey, a kind and clever bank teller, as they fell through time — even preparing to propose to her before an encounter with the same forces that appear in Loki left him with sad memories and a broken heart.
Astonishing Spider-Man & Wolverine focuses on the two titular superheroes who, after a chance encounter with the Orb during a bank robbery, results in a set of Time Diamonds being activated and flinging them both through time. First landing in the Cretaceous Era shortly before the asteroid hits the Earth, Spider-Man spends months making sculptures of a mysterious woman he sees in his dreams. Notably, it isn’t Mary-Jane Watson, Gwen Stacy or any other notable figure from Parker’s life. He doesn’t even know her, but he knows she’s important to him. The two heroes are repeatedly shunted through the course of history, repeatedly facing off with the Orb and watched over by time-traveling brawlers known as Czar and Big Murder.
Across the course of their adventures — which are revealed to be the manipulations of Mojo to create a new show for his adoring public — Spider-Man’s dreams are revealed to be tied to an upcoming “love interest” Mojo has intended for the wall-crawler. This turns out to be Sara Bailey, a bank teller at the same bank where Spider-Man and Wolverine were dragged into the conflict. His dreams about Sara even helped save the world, as it gave an anchor for Spider-Man to share with a Phoenix-possessed Wolverine, bringing him back to Earth and keeping him from wiping out all of existence. The Minute Men arrived to capture the various time-travelers, but in the chaos missed the two heroes and Sara, who found themselves tumbling through time once more.
Spider-Man, Wolverine, and Sara find themselves transported into the 19th century with only one depowered time diamond. The three make do with this change, unsure if they’ll ever be able to return to their original timeline. Together, they spend over three years adjusting to their new home. Logan finds a place with a local Native American tribe, while Peter and Sara fall in love. In those years, Peter adjusts to running an apothecary and becoming an “outlaw rustler,” defeating rogues with old west variants of his classic Spider-Man equipment. Meanwhile, Sara opens up a bank, with Peter hypothesizing that she’ll one day become a major business mogul herself. Peter reveals he kept the last time diamond — seemingly depowered from their adventure — and that he intends to give it to Sara as an engagement ring.
Spider-Man genuinely loves her, and wants to spend the rest of his life with her, regardless of what era they’re in. But when he shows Logan the ring, it finally serves as a beacon to the Time Variance Authority, who arrive on the scene to send all three back to their proper place in time. While Spider-Man and Wolverine were allowed to retain their memory of the adventure, however, Sara was restored to her proper place in the timeline and lost all recollection of their adventure — leaving a heartbroken Spider-Man to leave the scene. For such a bizarre and often madcap story, it’s a surprisingly somber finale for Astoniashing Spider-Man and Wolverine — with Peter losing out on the chance to be with a woman he seemed to genuinely love just as much as any of his mainline love interests.
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