Supernatural Which moment(/memory) was the most heartbreaking [for Dean]?

Pick one:
Seeing Sam celebrate Thanksgiving with his 'girlfriends' family.
The night Sam left for Stanford.
little!Dean comforting his momma! (Mary ;))
Sam having a dog, and enjoying life when he ran away.
is the choice you want missing? go ahead and add it!
 Dean-girlx posted over a year ago
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