Lewis: My ankle will never be the same because of you.
Jonathan: What? I just saved your life.

(to Jonathan) Let's go have a drink and get drunk. Sixteen gin and tonics.

Ray

Jonathan: Why didn't you write a second novel?
Jonathan's client: Because I was afraid to.

I suck at everything.

George, you're being way too hard on yourself. It's not good for your immune system.

Jonathan: What's your secret?
Kidnapper: Never go to bed angry. Pass this on to you.
Jonathan: Come on that's your secret? Never go to bed angry?!

Kidnapper: Do you have any rich friends?
Jonathan: Yes, I have one, but I really don't think I should involve my friends.

Jonathan: Oh my God! What is that?
Ray: I've got long foreskin. Not everybody is Jewish ya know.

Can you please look at my penis and tell me I'm an adult male.

I think I may have the smallest penis in the world.

Jonathan: George, why are you having an affair with your ex-wife?
George: Because I've never fallen out of loved with her.

The meat packing district really has become Los Angeles.

Bored to Death Quotes

(to Jonathan) I hope your heart is broken many times because it means you would have loved many times.

Dimitri

Men face reality. Women don't. That why men need to drink.

George