Jen and Pyper were once close friends when they were young children. As time went on, Pyper began to realize that she had feelings for other women, particularly Jen. While they were in elementary school, Jen came out to Pyper as lesbian, further cementing her feelings toward her. Pyper was overjoyed to learn she wasn't alone in feeling the way she did about other girls, but their shared affection did not last long.
Pyper's father was a pastor at a prominent Christian church and forced a strong ideal of homophobia onto his daughter. She was initially physically dragged away from Jen before her family's negative views toward LGBTQ people fully took hold. She was regularly preached to that being a lesbian was soulfully wrong and became fearful of following her true identity out of fear of damnation.
By the time high school came about and the comic's story began, Pyper had devolved from Jen's close friend to a self-righteous bully, regularly chastising her and Max for their LGBTQ identities and their falsely-presumed relationship with each other. However, Pyper was internally hurting more from their interactions than her targets were, feeling increasingly resentful toward their ability to be open about their sexuality while she was forced to repress her own.
This resentment ultimately caused her aura to become dark and corrupted, attracting one of Devoid's minions to feed off her self-hatred and despair. While Max was first trying on the chest binder Jen bought him for his birthday, the leak in the seal to Devoid's prison caused an earthquake that sent Pyper toppling onto Jen. She attempted to be disgusted by her insinuations when Max noticed the beetle-like spirit on her back. However, since it was too small for those without his powers to see, she assumed he was messing with her and told him and Jen off, calling them degenerates.
She ran into the two later that evening at the Bubble Tea House and resumed her chastising, when Jen retorted one of her insults by calling Pyper a mistake. Pyper was extremely angered by this and her aura reached severe saturation of negativity. Max spotted the beetle again and chased it out of the restaurant with Jen in pursuit of her friend. Still angered by Jen's earlier comment, Pyper stormed away from her own friends and chased them outside. After her tainted light triggered an enraged emotional meltdown, the spirit consumed her light and rendered her unconscious while Max fought the monster. Meanwhile, Jen attempted to save her as well, but the two were stuck to a lamp post together by the spirit's webbing.
When the monster was defeated and Pyper regained consciousness, Max confronted her about the obvious internal issues she was stockpiling and started to admit to earlier. Pyper broke down crying, fully admitting that she hated how her family and their beliefs viewed her identity as sinful and that she was jealous of them the entire time. Max and Jen did their best to console her until she regained a calmer emotional state, with Jen going with Pyper to make sure she got home safely after the ordeal.
The next day at lunch, Pyper's friends began picking on Max for his new haircut and accused him and Jen of doing "unspeakable things" after dashing out of the Bubble Tea House, only for Pyper to stop them by stating that the two weren't worth their time. Before returning to the others, Pyper and Jen shared a concerned glance, leaving Max somewhat confused about how things stood between them. Jen's sole response before changing the subject was not to worry about it.
A few days later, Max spots Jen heading into an alley by the school and tries to get her attention. When he follows her around the corner, he finds her with Pyper, holding hands as their auras turn pink (indicative of their emotional states). The two girls grow flustered and pull off each other as Jen flusteredly attempts to explain. Pyper chimes in by declaring she wants to officially join Team Magical Boy to prove her father wrong for blaming the phenomena caused by the monsters on sinners, and likewise wrong about who she is. After the group discusses plans to close one of the opened gates imprisoning Devoid, Max confronts Jen about her involvement with Pyper. Jen confirms that Pyper has been taking their advice to heart and coming to accept herself for who she is.
Later that day at lunch, as the team concocts their official plan to close the gates, Pyper's friends chastise her for hanging out with the "degenerates," making a point to ask what her father would think. When they call her a hypocrite for joining in their opposition of the group before, Pyper admits to being in a bad place back then and formally asks Max and Jen to forgive her. When her friends snap that she's dead to them and storm off, Jen tries to comfort her.
During their raid on the gate in the woods, Pyper is the first to discover one of the spirits and blasts it with bug spray, followed immediately by Jen bashing it with a baseball bat and asking if she's okay, complimenting Pyper on her clever weapon choice. The monster is revealed to still be alive and Pyper startledly leaps behind Jen.
The ship sailed in response to the two once having mutual feelings for each other and the significantly improved standing of their relationship since Pyper's initial arc. However, it began to form in readers' minds a bit before these developments as a result of a couple earlier instances of shiptease, primarily the earthquake and Pyper's clearly flustered reaction to the incident.
While the status of their relationship is not explicitly confirmed, their interaction in the alley leaves little room for doubt that they are at least exploring their feelings for one another.
On the official poll for which ship should receive its own wallpaper, the ship was the most popular containing either Jen or Pyper, as well as the third most popular ship overall.
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