Hey Liz, just saw the Cat's Cradle solitary Dean edit you reblogged, read your tags and mm for me I always just assumed it was bc she was kind to him. Made him want to be someone he couldn't be? you know? I'm sure he adored her but I think part and parcel of it was kindness and the fact that we (ppl) fall for the ones we feel we can't keep. What do you think?
had to go digging, but here is the post, and here are the relevant tags:
#i feel like not enough is made of those solitary years #we know that sam was at school and we can fill in the blanks #but how much was dean hunting alone #how often did he and john work together #and how often was it just a phone call here or there #how did he turn into the guy #who knew a girl for like three weeks and decided he was in love #that's insanity
I think your assumption about Cassie is a perfectly solid headcanon. We know basically zero about that relationship, other than that: she was a spitfire, they had great sex, and it was really short before he spilled the extremely closely guarded family secret and she--pretty reasonably, in my opinion--kicked him out. Of course, that it turned out that ghosts and shit were real must have been quite the mindfuck, once the Route 666 episode rolled around.
My headcanon is that she probably was kind to him, but probably more that... she just talked to him. She looked at him, and saw someone worth keeping around, even if only for a few weeks. How much Dean must have deeply appreciated her, and needed that, for him to tell The Secret and crack himself open like that. (Sam, after all, was getting ready to marry Jessica, and never spilled a word; bought a house with Amelia, and not a thing. That’s how big the Secret is.) Also note that Dean throughout the early seasons counsels that you never, ever talk to a ‘civilian’ about the life--you don’t just bring someone into that, not when they don’t matter. So--Cassie must have really, really mattered. Moreover, Dean must have really, really needed something that mattered.
As part of this headcanon, I suspect he thought it was a big mistake, once all was said and done. A great girl, an amazing one, one that he maybe could have seen himself really tying himself to--but, no. In the end, that never works. (See: Lisa.) Their lives were too different and he was never really going to make it work with her, was he. He offers up a tiny bit of hope, but she’s more realistic, and he can’t have thought leaving her was anything but a goodbye. This is really underlined by the way Sam says, at the end of the episode, You meet someone like her, doesn't it makes you wonder if it's worth it? Putting everything else on hold, doing what we do?--and Dean only smiles at Sam, and doesn’t seem sad or even particularly wistful. She’s a memory to be treasured, maybe. Someone who will live on, vibrant and gorgeous and smart and having her own real life, and thinking about her wouldn’t cause him any pain. That’s something, for Dean.