Love what Jess knows about Dean, and the lies Jess has caught him in a lot. I love the idea that Sam is so used to be spoiled by Dean, in these simple little ways like Dean always preparing food for him, that he expects it from everyone else as well.

Two pieces I'm not quite sure I understand, though:
According to Jared, he kisses just like Sam does, or more specifically Sam kisses just like he does.

I'm assuming Jared is a mutual friend - how does he know what Dean kisses like?

And I don't really understand the first piece of 5 things about Jess that remind Sam of Dean - sorry, I'm slow, but what's with all the t-shirts?

But yeah, loved these a lot. I like your Jess, she's fun and sweet and seems very suited to Sam, especially in her similarities to Dean.