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Just for fun I thought I would ask this question. Dean's death in the finale got me thinking, and although it was one of the saddest moments of the 3 season's it wasn't the saddest moment for me. That would have been Sam killing Madison in season 2, that made me cry and I am not ashamed to admit it .

I think All hell Breaks Loose (end of part 1, beginning of part 2) when Dean was holding Sam and screaming for him before he died/while dying PLUS after when he was crying and talking to Sams dead body right before he went and made the deal was one of the saddest moments

And John dying 

I agree with feliciaaa.

For me the saddest moment was in the episode 'Home' from season one when Mary appeared and talked to Sam and Dean.

Now I am going to go with a non traditional answer and say this seasons episode that marked the episode that had the return on the Trickster and before the Sam "learned" his lesson of no matter how hard Sam tried he could never save Dean.  Another one from this past season is when it seems like the ex girlfriends son is not Dean's.  I still am hoping we might find out it realy is his.  As being a person whos first dad pased away when I was young kinda hit home in knowing I am the only link to that part of my family tree.

  

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AKalel:

Another one from this past season is when it seems like the ex girlfriends son is not Dean's.  I still am hoping we might find out it realy is his.    

I'll be honest, I came to this series rather late so am not up with all the early episodes but I thought this was sad too. In that melancholy sad way. Dean realized that thanks to their "job" he'll likely never have a normal family life with kids and the whole white picket fence.

AKalel:

Now I am going to go with a non traditional answer and say this seasons episode that marked the episode that had the return on the Trickster and before the Sam "learned" his lesson of no matter how hard Sam tried he could never save Dean.  Another one from this past season is when it seems like the ex girlfriends son is not Dean's.  I still am hoping we might find out it realy is his.  As being a person whos first dad pased away when I was young kinda hit home in knowing I am the only link to that part of my family tree.

 

 

i think we may never know if Ben really is Dean son 

Saddest moment, Bela's apparent demise.  If permenant, it will cut down on the whining on the net.

 On the upside, she did end up in Hell about the same time as Dean so it is possible they will team up raise some Hell. 

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WHO:

Saddest moment, Bela's apparent demise.  If permenant, it will cut down on the whining on the net.

 On the upside, she did end up in Hell about the same time as Dean so it is possible they will team up raise some Hell.

I was going to say the saddest moment for me was when Bela was introduced... her "apparent demise" actually brought a Grinch-like twitch to the corner of my mouth, around the same time the audible little snicker emerged.

That would be a kicker, eh? Dean having to team up with Bela to get out of Hell... I can see Dean double-crossing her at the last second and leaving her to rot/burn there, though.

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"Something, something, something, Dark Side... something, something, something, complete!"

 her "apparent demise" actually brought a Grinch-like twitch to the corner of my mouth, around the same time the audible little snicker emerged.

That would be a kicker, eh? Dean having to team up with Bela to get out of Hell... I can see Dean double-crossing her at the last second and leaving her to rot/burn there, though.

LOL That was my exact reaction. Glad to know I'm not alone. As long as he leaves her in hell when he leaves I'd be okay with that. And I guess not having her to *** about would be a loss for some people.

WHO:

Saddest moment, Bela's apparent demise.  If permenant, it will cut down on the whining on the net.

 On the upside, she did end up in Hell about the same time as Dean so it is possible they will team up raise some Hell. 

 

nah not Bela, did she ever REALLY help them? I mean she tried to get out of her Dean by stealing their best weapon and trying to shoot and kill Sam and Dean before her deal was up.

If anyone teaming up in hell maybe it would be Dean and Ruby, she's more helpful (former witch + demon, is better imo) not to mention she hot out of hell once before AND she was trying to 'help' them already (though she may have a secret evil motive we dont know yet) 

feliciaaa:

WHO:

Saddest moment, Bela's apparent demise.  If permenant, it will cut down on the whining on the net.

 On the upside, she did end up in Hell about the same time as Dean so it is possible they will team up raise some Hell. 

 

nah not Bela, did she ever REALLY help them? I mean she tried to get out of her Dean by stealing their best weapon and trying to shoot and kill Sam and Dean before her deal was up.

If anyone teaming up in hell maybe it would be Dean and Ruby, she's more helpful (former witch + demon, is better imo) not to mention she hot out of hell once before AND she was trying to 'help' them already (though she may have a secret evil motive we dont know yet) 

This is off-topic I suppose but IMHO I think the first couple of episodes of Season 4 will feature Dean & Ruby trying to hatch a plan to escape from hell so I agree with you there WHO.

Now back to the topic at hand, the saddest moment for me would be the end of "All Hell Breaks Loose: Part I" as someone else already mentioned. 

 

Definately when Sam had to shoot Madisan.

 

I love this show! I actually cry a lot while I'm watching it. It's a running joke in my family.

My saddest moments ha already been mentioned.

Sam shooting Madison (didn't know her all that long but they could have been such a great couple)

Absolutely the Season 1 finale where Sammy dies in Dean's arms and the beginning of Season 2 where Dean's talking to Sammy's body and then he starts asking what he's supposed to do now that Sammy's gone.

Dean screaming for Sammy at the end of Season 2 finale when he's in Hell.