SHEPHERD

Penelope Text: "Keeping Blair home while you do horrible things. Serena Plan!"
Serena: "Dan! I hope you don't read Gossip Girl right now while I'm standing here..."
Dan: "She was just Spotted at the Empire? Man."
Serena: "She's probably just reiterating that she and Chuck are broke up for good. PS, this is what my unconvincing lie face looks like. Serena Plan!"

Then something marblemouthed that I bet is a very funny line, but even after listening to it six times still sounds like, "Come on, let's galoonytunesy alimony while we wait."

EMPIRE

Bart: "Hey, I just happened to pick up your engagement ring that you got killed for. I was there buying Lily a present to celebrate our annulment."
Lily: "Hey guys! I'm here to complicate everything."
Chuck: "Cool, I will just Gollum about this engagement ring for a while."
Minion: "And I will take a picture of you doing that. Serena Plan!"

WALDORF

Eleanor: "Despite my best efforts, and those of this show for the past two years, you have turned out pretty awesome at the last second."
Blair: "We are headed for a reckoning!"
Eleanor: "You think you're Jane Austen again, huh?"
Blair: "I'm growing out of drama, for real. It's a legit question, though. I like Dan for so many reasons, like he doesn't hit me or sell me for things. And then I also like Chuck, who hasn't done those things either. It's a morass! A reckoning, I say again, is nigh!"
Eleanor: "Which kind of love is better? Perfect In-Your-Head Love, or Mindless Self-Destructive Passion Love? Dawson or Pacey? Angel or Spike?"
Blair: "If only they were a single entity, or I made better choices. If only I'd never seen The Philadelphia Story."

Eleanor: "You are a Powerful Woman. You forgot it, but we didn't. How would you like to be my CEO at Waldorf Designs?"
Blair: "Wait, for real? Because I believe in fashion, you know that I do."
Eleanor: "Then I'm retiring, and you can just hire a great designer as your first job."