Conrad Hilton to Don Draper in Wee Small Hours (Season 3, Episode 9):

You’re like a son. In fact, sometimes you’re more than a son to me because you didn’t have what they had and you understand.

Betty Draper to Don Draper in The Gypsy and the Hobo (Season 3, Episode 11):

I knew you were poor, I knew you were ashamed of it. I see how you are with money, you don’t understand it.

I love this show.