Honestly, I'd never considered this before you mentioned it. I think, maybe, because Christopher was barely around, almost an afterthought. But yeah, this really makes sense! Like, they never seem to know what to do when a guy "stays" because Christopher never stayed. A level of self-sabotage just kicks in right around that time. And they both always have this longing for "the one that got away," to the point that they delude themselves into thinking certain guys—cough, Dean, cough—are this guy, when really they should be saying good riddance instead.
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Honestly, I'd never considered this before you mentioned it. I think, maybe, because Christopher was barely around, almost an afterthought. But yeah, this really makes sense! Like, they never seem to know what to do when a guy "stays" because Christopher never stayed. A level of self-sabotage just kicks in right around that time. And they both always have this longing for "the one that got away," to the point that they delude themselves into thinking certain guys—cough, Dean, cough—are this guy, when really they should be saying good riddance instead.