Ellen… The mother he never had
Ellen Harvelle scared the living daylights out of Dean, and with good reason. She defends her daughter fiercely, even to the point of killing someone. Dean, nor anyone else, is an exception.
Still, Dean will never forget Ellen. Her badass attitude and strong-willed demeanor will stay with him forever. There are many memories he has with that woman. The most powerful, however, is of one he has from before the night she and Jo died. It was just after the picture was taken.
Everyone was asleep (except for Cas, who had gone out for a good-old-fashioned flight), leaving just Ellen and Dean alone in front of the fire, sipping whiskey and pondering the battle that lies ahead, "I've never actually been a soldier," Ellen comments.
Dean looks at Ellen, "What?"
"I've never fought in a war. My husband was the one who did the hunting. He had training from Vietnam," Ellen explains before she takes another swig of her drink, "He taught me everything I know,"
Dean shrugs, "Could've fooled me." Then he swallows more of his whiskey.
Ellen smiles, letting out a small laugh. "You flatter me, Dean. At least tomorrow, I get a chance to see what my husband went through all those years ago."
"You'll do fine, Ellen," Dean replies. "You're the toughest chick I know."
Ellen laughs again, "And you are the smoothest dick, I know." Her eyes twinkle mischievously. She stands up in front of the fireplace, "Now," she says confidently. "I have a toast to make."
Dean laughs at her a little, knowing she is more than a little tipsy.
She holds up her glass, "To the return of the old days. To the fall of Satan. To the survival of the human race. And—" she holds her glass up higher—"to family. May my daughter and the two sons I wish I had live the long, healthy, happy, possibly normal lives they deserve."
Dean hesitates for a moment. Her little speech, though produced while drunk, touches him a little. It makes his heart—hot with the rush of whiskey—warm with a little tenderness toward Ellen. He smiles up at her, his eyes softening a little as he raises his glass, "Cheers."
Then they both swallow the last of their whiskey. As he was sleeping that night, little toast from Ellen clings to Dean's mind, embedding itself into his consciousness.
A few weeks after they died, Dean remembered that moment with Ellen. It made him tear up as that memory always will. It is the best memory he has of his surrogate mother.
And he'd rather have that one drunken memory, than of a million other minor, sober memories. Because it is in that fuzzy, drunken memory that he remembers Ellen Harvelle's face the most.