They send Jenny into PRADA so she can go through all of Lily's drawers and steal her pills, like back in the day when she was a drug pusher. It's so dumb because she's like, "What exactly am I looking for?" And they're like, "A bottle of pills, you halfwit. It looks like a bottle with pills in it. You are the worst motherfucking drug pusher." So while that goes down, I would like to perform a monologue. "She's totally failing me on purpose, because I didn't join those stupid Mathletes! She was so queer, she was like, I'm a pusher, Cady. I'm a pusher. What does that even mean? Like a drug pusher? Probably. She said she works three jobs, I bet she sells drugs on the side... To pay for her pathetic divorce." Blair is on fire with the total mach five drama of how Holland is "obviously" poisoning Lily, so she can have Rufus all to herself. "So Shakespearean!"
This is where the dumb writing really shows up, because Nate is just handed these ideas of jokes that are not actual jokes, like, "Wouldn't it be funny if Nate said something like this," but they never actually filled in the blanks. Or maybe it's the acting. Either way, I hate this shit. He compares it to Fatal Attraction and shivers about the idea of dead bunnies. And they think about telling Lily about all this, but Chuck radically is not having that: "Jenny tried to sell your mislabeled meds, which somehow came from the woman who said she slept with your husband?" It's a mouthful.
So they discuss what is going to happen for awhile, which is that they will blackmail Holland at this benefit, and everybody leaves to go get dressed for the thing. And once again, Nate gestures toward an idea of something funny without actually having anything funny to say, by way of explaining how often they do these massive sting operations: "Last year Georgina pretended to be this rich Canadian to get Poppy, but things got all messed up when she turned her back on Jesus!" Which would have been so funny, if they'd actually written the joke instead of just pointing at the general location of what's funny and asking us to do the work ourselves. You could just throw a random Dorota in there and some fucking waffles and fatwas and really go to town.