Chuck's never seen a black person of authority on this show before, so he naturally assumes Raina Thorpe is a secretary or flagstone-polisher (or scarf-stealing, cancer-faking psychiatrist) when he goes to meet her father. (Complete with leadup to one of those distractingly embarrassing "only-on-Gossip Girl" moments where Raina makes a grammar mistake in the middle of hectoring Chuck about precision in speech. I mean, at least it's not Blair this time, but can we get this staff a Garner's, please?)
Anyway, it's sort of flirty and mostly weird and class-issues ("fetch me a coffee and the current issue of Pravda") and finally Raina's like, "He's not even in town yet, so stop bugging me. And I will tell you -- because I never lie, it's my one trait -- that Bass Ind. is totally getting sold in the next 24 hours. See you at the Thorpapalooza tonight, Chuckles." Between being caught out of the loop by a mere whatever-she-is and this latest news, Chuck's face goes from doing that thing to doing that thing hardcore.
Lily admits that she ambushed Family Brunch, but she and Rufus agree that two weeks of silence is more than long enough. And I'll admit, this episode is sort of annoying, because all the parents end up right and all the kids end up wrong, and that's totally unrealistic, not to mention a fucking retrograde bummer, but I did some thinking about it and I realized that it does sort of make sense how this plays out:
Lily, having been left in the lurch by her entire family last time for her sins, is attempting to make it up to everybody with a grand gesture -- very Humphrey of her -- but because she knows the value of propaganda better than S ever is, she knows she has to unveil it at the pinnacle and not before. If Chuck and Serena are going to love her again (and if Rufus and Eric are going to come back to her side), it's gotta be fucking big. So this whole episode, she's doing secret things to save Bass Ind. and get Ben out of jail, but she won't tell them this until it's done.
Which rankled me at first, because it seems like needless complication and lazy writing, and maybe it is, but there's also the entire mandate of this show, that says we arrange our personal propaganda to greatest effect even when we don't know we're doing it. And she's right about the grand gesture: Serena and Chuck would be twice as likely to come back to her if they got blindsided by her secret kindness.