Death Takes A Holiday

 
Dean doesn’t remember Tessa when they first cross paths. She even asks, “Don’t you remember me?” Apparently, that’s not the first time Dean has heard that.


 

“Honestly, if I had a nickel for every time I heard a girl say that…”
 

On The Head of A Pin 


Dean is in a VERY bad place, but his isn’t so far gone that his sense of humor has left him. After Castiel and Uriel demand his torturing skills with Alastair, Dean has had enough with Uriel’s presence and wants to talk to Castiel alone. Uriel agrees to leave, to see if there are new orders, but Dean can’t let him go without giving the final word. 


“Well, get some donuts while you’re out.”
 

It’s A Terrible Life 


Dean's memory is wiped, so he doesn't realize he's knocking down his brother when Sam tells him he feels like he was destined to do something else.  Still, for all of us worker bees out there, this coming from a big ego middle level manager, it's harsh.



“I think most people who work in a cubicle feel that same way.” 


 

The Monster At The End of This Book


The fact that Dean was taking the publisher’s fan girl moments so well is funny enough. So when she asks him how often he cries like that, Dean comes up with something way better than telling her that he does. 

 

“Well, right now I'm crying on the inside.”
 

It just doesn’t get any weirder than this.



 

“I'm sitting in a laundromat reading about myself sitting in a laundromat reading about myself. My head hurts.”