Jack: I think Angie is right-handed so you have to work her clockwise.
Liz: Wait, you've already thought about fighting her?
Jack: Every time I meet a new person I figure out how I'll fight them. You have a gimpy right knee, right?

You are a puzzle, Kenneth Ellen, and I'm going to solve you. Yes I am.

[on treating Liz differently] Well, I pay you a little less.

Boston is the greatest city in the world. Boston Tea Party, Boston Cream Pie, Boston Rob Mariano.

Liz: Well it was nice of you to let him keep his job.
Jack: The Italians have a saying, Lemon. Keep your friends close and your enemies closer. And although they've never won a war or mass-produced a decent car, in this area they are correct. In five years we'll all either be working for him... or dead by his hand.

Lemon, women your age are more likely to get mauled at the zoo than get married.

Jack

Jack: Oh, come on Lemon, what is this? A green card thing?
Liz: No.
Jack: Closet case?
Liz: I don't think so.
Jack: Slump buster?
Liz: No, he's not a ballplayer.
Jack: Bundy-esque serial killer?
Liz: That was my first thought, but no. This is actually happening, and I'm blowing it.

Jack: Lemon, I want to thank you. For showing me that I could have a pleasant evening with a woman my age.
Liz: I'm twelve years younger than you.
Jack: A woman your age then.

Liz: Before I go, could I at least find out what Frank's hat says.
Jack: "Constant Craving."
Liz: He could do better!

Jack: Alfredo. 2 p.m.
Liz: I'm not dressed for that.
Jack: You're dressed for Burger King. Should we make it Burger King?

Way to tell me something I already knew. What are you, The Huffington Post?

I have a betting system based on horse penis size.