Roger Sterling: I bet daily friendship with that bottle attracts more people to advertising than any salary you can dream of.
Don Draper: It's the way I got in.
Roger Sterling: So enjoy it.
Don Draper: I'm doin' my best here.
Roger Sterling: No, you're not. You don't know how to drink. Your whole generation, you drink for the wrong reasons. My generation, we drink because it's good, because it feels better than unbuttoning your collar, because we deserve it. We drink because it's what men do.
Don Draper: What about shaky hands, I see a lot of that with you boys?
Roger Sterling: No joke. Your kind with your gloomy thoughts and your worries, you're all busy licking some imaginary wound.
Don Draper: Not all imaginary.
Roger Sterling: Yeah, boo hoo.
Don Draper: Maybe I'm not as comfortable being powerless as you are.

Bert Cooper: [to Pete] The Japanese have a saying: a man is whatever room he is in, and right now Donald Draper is in this room.

Don Draper/Dick Whitman: [holding out Meditations in an Emergency] Did you read it?
Anna Draper: I did. It reminded me of New York. And it made me worry about you.
Don Draper/Dick Whitman: What about the cards? Should I be worried?
Anna Draper: It's all here. You're definitely in a strange place. But here's the Sun.
Don Draper/Dick Whitman: [points to Judgement card] : That can't be good.
Anna Draper: It is.
Don Draper/Dick Whitman: It's the end of the world.
Anna Draper: It's the resurrection. Do you want to know what this means, or not?
Don Draper/Dick Whitman: No, I don't. I can smell the ocean.
Anna Draper: [points to the World card] This is the one.
Don Draper/Dick Whitman: Who's she?
Anna Draper: Shes the soul of the world. She's in a very important spot here. This is you; what you are bringing to the reading. She says you are part of the world. Air, water, every living thing is connected to you.
Don Draper/Dick Whitman: It's a nice thought.
Anna Draper: It is.
Don Draper/Dick Whitman: What does it mean?
Anna Draper: It means the only thing keeping you from being happy is the belief that you are alone.
Don Draper/Dick Whitman: What if it's true?
Anna Draper: Then you can change.
Don Draper/Dick Whitman: People don't change.
Anna Draper: I think she stands for wisdom. Once you live, you learn things.

Betty Draper: Where have you been? You disappeared.
Don Draper: I had to have some time to think about things.
Betty: Must be nice. Needing time and just taking it, all on your own terms, not wondering what anybody thinks. Me, the children.
Don: Bets, I'd do anything I could to undo what happened.
Betty: What happened?
Don: I was not respectful to you.
Betty: Well, now I know I'm not crazy, that helps.
Don: I can't walk away from this, I want to be with you, I want to be together again.
Betty: [shakes head] I don't know. Honestly, things haven't been that different without you.

Roger Sterling: What you did is totally unacceptable.
Pete Campbell: I realize that.
Roger Sterling: I want you to be very clear about this: You were fired. I wanted you out. Cooper wanted you out. And you would be...if it weren't for this man. [motions to Don] He thought you deserved another chance. That's right. He fought for you.
Pete Campbell: I don't know what to say.
Roger Sterling: Say nothing. You are here because of Don Draper's largess.
Pete Campbell: Thank you. Thank you so much.
Roger Sterling: Now, I know that your generation went to college instead of serving, so I'll illuminate you. This man is your commanding officer. You live and die in his shadow. Understood?
Pete Campbell: [nods vigorously] I won't let you down, Don.
Roger Sterling: Jesus! Campbell...don't ever say that.

Bert Cooper: I don't want to have to walk down here every time we lose an account. This is an advertising agency. I'll wear out the carpet.

Betty Draper: [To her psychiatrist] I don't know why I'm here. I mean, I do, I'm nervous, I guess. Anxious. I don't sleep that well. And my hands. They're fine now, it's like when you have a problem with your car and you go to a mechanic and it's not doing it anymore. Not that you're a mechanic. I guess a lot of people must come here worried about the bomb. Is that true? It's a common nightmare, people say. I read it in a magazine. My mother always told me that it wasn't polite to talk about yourself. She passed away recently. I guess I already said that.

Bobbie Barrett: [to Peggy] You're never gonna get that corner office until you start treating Don as an equal. And no one will tell you this, but you can't be a man. Don't even try. Be a woman. Powerful business when done correctly. Do you understand what I'm saying, dear?

Anabelle: You were the one.
[[w:Roger Sterling|: You weren't.

Anna Draper: I started thinking of everything I was sure was true, and how flimsy it all might be.
Don Draper: You don't have to see a UFO to know that. But it's not a great way to think about things.
Anna Draper: I know everything about you and I still love you.

Allison: Good time? Bad time?
Don Draper: Yes.

Doctor: So, Mr. Draper, you haven't had a physical in quite some time.
Don Draper: Yeah. I eat a lot of apples.

Betty Draper: [to her daughter] You don't kiss boys. Boys kiss you.

Betty Draper: There's a difference between wanting and having.

Betty Draper: What would you do if you were me? Would you love you?
Don Draper: I was surprised you ever loved me.