Actually, I think part of Dean really does want that life —he just doesn't know how to live it, and if he did know how, he wouldn't want to have it without Sam in the picture somewhere.
I don't think Lisa ever meant for Dean to stay forever and ever and be her true love, or whatever. I think she saw a friend who was in pain and wanted to help him, in whatever way she could.
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Actually, I think part of Dean really does want that life —he just doesn't know how to live it, and if he did know how, he wouldn't want to have it without Sam in the picture somewhere.
I don't think Lisa ever meant for Dean to stay forever and ever and be her true love, or whatever. I think she saw a friend who was in pain and wanted to help him, in whatever way she could.