Sam Winchester and Dean Winchester Oh my pudding shirt

I personally think sometime after Sam left for Stanford. Sam Winchester and Dean Winchester Oh my pudding shirt Sam is surprised to hear that Dean goes on solo hunts, so that’s something he hasn’t done when Sam was around. Solo hunts mean Dean would need his own vehicle, so John probably gave him the Impala and got himself that GMC truck he was driving. Dean was looking out for him pretty much and made sure Sam was always fine. He only went back to hunting because Dean came for help to find John and then his fiance got murdered by yellow eyes. Once that happened he became self-destructive with the demon blood and thinking it was the right way even though it really wasn’t. Dean on the other hand was always somewhat self-destructive in his early to late teen years. With flashbacks, we see he was a womanizer even as he got older he stayed the same.

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