I finally get some time to go back over your PILOT comments and love to keep the conversation going.
“I struggled to like Sam until about season 7, and it began with the Pilot. If he supposedly loved Jessica, why didn’t he tell her who he truly was? I know John had a “rule” about that, but since when did Sam obey ANY of John’s rules? Dean told Cassie who he was, and he was religiously obedient to John and his rules. Dean loved Cassie, even though he’d only known her for a short time. When you love someone, you tell them the truth about who you are — especially if you have a dark or dangerous past. Sam was supposedly going to propose to Jessica — BAH! I’ve often wondered if Sam initially left with Dean for his OWN reasons. He’d been having visions of Jessica burning up on the ceiling for days before she died. Maybe he wanted to find John to get answers to that, and not really to save John. I don’t know – I just found Sam selfish and unlikable for the first several seasons. Jared’s acting was clunky at times, which didn’t help. Jensen was already SO velvety smooth, that it just made Jared’s inexperience more apparent. And sorry, but it was kinda sleazy for Jessica to come into the room like that. If you hear a burglar breaking into your house, or you hear your boyfriend talking to another man in the middle of the night, by all means, enter the room wearing next to nothing. Classy. Enough of that.”
I’m not saying Sam wasn’t still very much a selfish child at times in the early seasons!! And rebellious as all hell. YES! But I can sympathize with it in many ways. Of course you are supposed to tell the person you love the truth….but in Sam’s specific case I simply think he was partially embarrassed by his strange and dangerous past and didn’t want to drive a new love interest away with it and partially he probably wanted to protect Jessica from possible danger. Was that smart? NO. Was that the right thing to do? NO. But Sam at that point was under the impression that his dad had thrown him out instead of being proud that his son got into a GREAT school on his own smarts AND he was probably under the impression that his brother wasn’t standing up for him to help him convince John. As we find out over time the Winchester Family also completely SUCKS at communicating emotional truths, so to me all this leads to the understandable as circumstance why Sam was looking for a “clean slate”. Obviously that action proofed foolish pretty quickly and deadly for Jessica…..and I do think that Sam carries that failure with him for a long long time.
I do find your point about Sam going with Dean to get answers from John about his visions VERY intriguing! I could totally see that as an additional motivator!!
True that Dean was honest with Cassie!! And I always applaud him for that, however, he obviously also lacked communication skill in that confession because we find out that Cassie thought he was nuts or lying to get rid of her and he didn’t seemed to have followed up and tried to smooth the situation over or keep a relationship going. You KNOW I love Dean, but he is not exactly emotionally mature at the beginning of the show either. Telling a girl he spends a few months with the truth about who he really is when he knew very well that he wouldn’t stay with her was in a way not much of an emotional risk. And after all even after reconnecting with her SHE is the one realistic about their impossible future….and he obviously doesn’t try to show her differently.
All I’m saying is that both brothers have their issues with relation ships and lack the ability to navigate the necessary emotional give and take successfully.
But it’s exactly THAT which makes them such interesting and relatable characters to me. So I forgive them.