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Question meme via
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On the one hand this was hard to pick because every moment Rey and Kylo are on screen together is my favourite shippy moment, but on the other hand there's one really obvious answer which is the moment that first set me seriously shipping them: the aftermath of the throne room fight scene in The Last Jedi, when Kylo asks Rey to join him in ruling the galaxy.
I cannot even TELL you guys how hard this scene hit me when I first saw it in the cinema. The Reylo vibes had been creeping up all movie, through a sequence of psychic bond moments that started out hostile and gradually became more and more intimate. That sense of togetherness, of mutual understanding, culminated in a breathtaking battle scene during which they fought almost like the two of them were one person, swapping weapons and watching each other's backs and at one point Rey even using Kylo's body as a springboard for her next attack. It seemed like an absolutely foregone conclusion that they were on the same side now, on the same page, ready to join forces for good.
And then, instead ... that. Not only are they not on the same page, they're not even reading the same book. Kylo's idea of the narrative he's living in is so wildly different from Rey's that there's no conceivable space for compromise: just like that, they're enemies again. But they both so desperately, desperately want not to be. They beg and plead (and in Kylo's case, viciously manipulate) with all their might, each hoping against hope that they can convince the other to abandon their convictions and change course.
IDK, man, I'm just so weak for unfulfilled yearning and the beautiful, self-destructive fuckedup-ness of simultaneously loving someone while actively wanting to destroy everything they stand for. The canonical soulbond by itself might have piqued my interest for a short while, but it's this scene in all its messy glory that tipped me over into Forever OTP territory.