CHEZ WALDORF

Parents: "Blair, where will you give birth to your child?"
Blair: "Lenox Hill, where I was born. As was my mother. And her mother before her. And so on."
Parents: "And for school?"
Blair, verbatim: "I've already sent a copy of the sonogram, along with an application, to Constance/St. Jude's."
(Everybody pretends that Constance Billard wasn't an absolute disaster for every single person that ever went there.)

Sophie: "While a New York education may be adequate for a non-royal, Grimaldis always attend boarding school in Switzerland. Furthermore, the child must be born in our wing at the Princess Grace Hospital Center in Monaco."
Eleanor: "I still don't understand that you are royalty and that our grandchild is going to be the ruler of an entire country one day."
Sophie: "It does seem to be a stumbling block for you guys."

BARNES OFFICE

Barnes: "Mr. Bass! I was just on my way out to do some Yom Kippur stuff. As a convert, the high holy days are really important to me, which I guess is why I'm only working a half day."
Chuck: "I really need some guidance. And by guidance, I mean a hand job."
Barnes: "Come right in. For a trained psychologist I sure am easily manipulated."
Chuck, verbatim: "Now, would you like me seated, or... Prone?"
Barnes, after a lot of this: "You are totally trying to fuck a psychologist in her office? That is maybe the most bizarre cry for help I've ever heard."

Chuck: "[An oddly anti-Semitic comment that makes you think about how this is a show about WASPs written largely by Jews, and honestly that should have gotten weird before now anyway.]"
Confused Gentile Privilege: "I am outraged on behalf of somebody else anyway!"