[Jack tries to teach Will how to be a good date]
I'm an expert. I go on literally thousands of dates a year.
That doesn't make you an expert, that makes you an escort.
S2 E15Advise and Resent
I know you're mad at me about what happened with Josh, but when you get down to it, aren't you mad at yourself for taking advice from someone who was half in the bag at the time?
So, really, I shouldn't be listening to you now.
Aw, honey...probably not.
S2 E16Hey La, Hey La, My Ex-Boyfriend's Back
[Jack is trying to talk Will into reuniting with his ex-boyfriend]
Look, if what's holding you back is your attraction to me, let me assure you: [points to self] It will never happen. Let that free you to pursue other, lesser men.
Oh, Jack...there are no lesser men than you.
When you and I broke up it was for different reasons. I wanted to raise the kids Jewish, you wanted to sleep with men...
I really do enjoy that.
S2 E17The Hospital Show
[An extremely young nurse enters to take Grace's blood.]
Isn't-- isn't there someone else who is a little more... experienced? Someone who didn't drive in... on a Big Wheel?
NPNurse Pittman
Oh, I don't drive. I keep taking the test over and over again, but I'm all, "This is hard!"
[Jack runs by.]
Gay ferrets to the waiting area. Gay ferrets to the waiting area.
S2 E18Sweet (and Sour) Charity
Give me one good reason that a man can't go out in a nice pillbox hat. [puts on hat and looks at himself in the mirror] Hello, reason. Oh, my God, there are actually pills in here!
[Jack and Karen walk into a homeless shelter]
Lord, look at these people. Why anyone would choose to be homeless is beyond me!
No one chooses to be homeless. It's because they did something bad.
S2 E19An Affair to Forget
[Will and Jack are planning Rob's bachelor party]
You know why we're blocked? It's because heterosexual marriage is just wrong! If God had intended a man and a woman to be together, he would have given them both penises!
I believe I heard Pope RuPaul II say that.
[Ellen has just found out that Rob and Grace once slept together]
RRob
Honey, it meant nothing! You know I don't like bony girls. It was like having sex with a cricket.
Oh, yeah? Well, I was fake chirping!
S2 E20Girls, Interrupted
VVal
My ex-husband wanted me to get a boob job, so I got rid of him. Well, that and the fact that he was sleeping with his dental hygienist.
Why is it always the hygienist? What is it? Is it the white uniforms, the latex gloves..?
VVal
I think it's because they're whores.
[Jack's latest intended conquest is an "ex-gay"]
They're trying to make gay people straight! Good Lord, don't they know what that'll do to the Fall line?
S2 E21There But for the Grace of Grace
Sorry, fruit, you're out of the loop.
So, the salad's done, the risotto is cooking. Let's talk wine. Karen, you have any preference?
Honey, I'd suck the alcohol out of a deodorant stick; so you're asking the wrong gal, okay?
S2 E22My Best Friend's Tush
Honey, love you like a cold sore!
These quotes come from Wikiquote's Will & Grace pages and are available under the Creative Commons Attribution-ShareAlike License.