Oh. My. God. I love this. You have broken me into tiny pieces. Because as much as I am a Sam/Dean OTP'er, I can see what Sam had with Jess, that he loved her greatly and she loved him back and the loss of that breaks my heart and makes me cry. This is wonderful and heartfelt and rings incredibly true, based on what we saw of them together and how he's held on to her for so long. Awesomesauce.