Grace: If you were any gayer, you'd be Elton John's fanny pack.

Grace: Jack, this isn't going to be as hard as you think. On some level, your mother has to know your gay. I mean, she has met you, right?

Grace: Jada Pinkett.
Will: Mmm.
Grace: Hate her.
Will: Wow, that's kinda harsh. I mean, she's not very...
Grace: Will, you know the rules. Love or hate. No gray area, just like life.
Will: Hate her.
Grace: Good boy.

Grace: Just F.Y.I. The first three letters in "assistant" spell "ass," so please get off yours.

Grace: Karen, I'm not gonna marry someone just because I want a nice apartment.
Karen: Um... yes. That- that would be wrong.
Grace: It would be settling. I want to marry "the one."
Karen: And well you should, honey. How else are you gonna get to the two and the three?

Grace: Karen... I wanna ask you something, but it's really personal, and I'm afraid you're gonna be insensitive.
Karen: Oh, honey. That makes me feel bad. Try me!
Grace: Okay. Do you think it's weird that I've had more partners but less actual sex than Nathan?
Karen: No. No, honey! That just means that people like having sex with Nathan and they don't like having sex with you!
Grace: I can't believe I hesitated to ask you about that.
Karen: Oh, relax, honey. I didn't mean it like that, of course I didn't! Listen to me! I just meant that people don't like having sex with you, okay?

Grace: Look, I'm sorry I'm not as strong as you all. I wish that I were. But I'm not. Will, your lover of 7 years left you and you have to live everyday knowing that he's out there loving someone else. I couldn't do that. I would die. And Karen, your husband is in prison. The rock of your life, and you don't know when you're going to see him again. If I were you, I'd be a total wreck. And Jack, you're so resilient, you're a 32 year old actor/singer who gets involved in a million different relationships, and never gets invested in any of them. I wish that I could do that, but I can't. I'm not like any of you. I just handle things differently, so please, just let me go back to bed, and deal with things the only way I know how.

Grace: Oh, my God. I know this apartment. You'll never guess whose it is. You're gonna die.
Will: We're all gonna die, Grace. The important thing is what you do while you're here.

Grace: Please tell me that you didn't drink your lunch yet.
Karen: Honey, I just got done drinking breakfast. You gotta give the liver a little time to digest!

Grace: So I repeated the joke. When you discovered "Hold me closer, Tony Danza," you rode that till the wheels fell off.

Grace: Sumner, hi. If you're looking for your Aunt Karen, she's not here. She doesn't work on days that end with... "day."

Grace: Well, you've come on a good night. Jack's mother is going to be joining us, and she doesn't know Jack's gay.
Karen: How could she not know? What is she, headless?

Grace: You and I, we have to stay focused. You know how sharks are eating machines? We are shopping machines. That means all we do is shop and poop. Shop and poop. Got it? So, what are we going to do now?
Nathan: God, I hope it's shop.

Grace: You know what the funny part is? [laughs] There is no funny part! My life is so unfunny, Mr. Hutt, it's not even... funny. I mean, what am I doing taking on a mortgage? I mean, my life is already a mess. I'm still renting an apartment, I don't have a driver's license, I'm not married, I live with a gay guy...
Will: Grace...
Grace: I haven't had sex in five months! And I was in Bloomingdale's this morning waiting in line to buy wrinkle cream, and this Jennifer-Love-Michelle-Sarah-Felicity-looking thing... bumps into me and says, "Excuse me...Ma'am." [sobs.]

Grace: You know, I thought I knew everything about you. But you're a mystery. Wrapped in a riddle. Surrounded by enigma. Growing boobies.