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If one is to engage with the primordial forces of darkness, one must expect a little social awkwardness
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Personally I think Rumple simply considers Milah & Killian to be true love, as it sort of lessens the blow of her choosing to run off with a pirate if it’s TL. I dont consider anyone to be TL until I see it confirmed either by TLK or A&E tell us they are TL (neither of which has happened for Milah & Killian, all A&E have said is they loved each other, so yeah.)
I agree that Rumple saw them as True Love (and said he didn’t reliase the power of True Love before). And seeing them is where he got the idea that True Love could be used in the curse. All he had to find was the epitome of TL and we get that with Snowing. Hook himself called Milah his first love, but he obviously loved her so much he was willing to spend hundreds of years trying to find a way to avenge her. That sounds like true love to me. If Charming is to believed TL is hard to come by and worth fighting for. Killian has fought for Emma, he didn’t really *have* to fight for Milah, but that’s not to say he didn’t love her any less. He’s a very passionate pirate. When he falls, he falls hard!
If one is to engage with the primordial forces of darkness, one must expect a little social awkwardness