Nate: Aren't you curious what it says?
Chuck: I think I can guess. You're a disappointment of a son; I'd die of embarrassment if I hadn't already; why do you wear so much purple?
Blair: Dear Son, I know I've always been hard on you—
Blair: —but my goal was always to prepare you for this day. To help you go from being a boy to a man.
Chuck: An Italian au pere took care of that.
Blair: Chuck, please. Sadly, there is nothing like the passing of a father to aid in this rite of passage for his son. Ultimately I do feel that I did my job and you are prepared for this next chapter of your...