They have set up Raina to be a really good romantic foil for both boys: She's just like Chuck, but Nate has figured out a lot of shit that neither of them have really figured out yet, because neither of them has ever punched their dad in the face. I never really thought about it, but in the context of being homeless and constantly punching his dad in the face and getting prostituted to literally every guest star that comes across the show, Nate has more actual perspective on life than anybody. Even Dan!
It is at this point that Raina takes a shower at the boys' apartment, puts on Nate's robe, agrees to play Black Ops with him, pulls out a joint from the robe, and decides to get high in the middle of the day instead of her meeting with Ivanka. This is Nate's idea of the perfect selling point, which for Nate it would be: "You know who gets really, really good weed? Chuck!"
"To old friends and new beginnings," we enjamb, as Lily and Russell drink a few bottles of wine and they talk about how Chuck did her so wrong. Apparently, Serena's not the only Rhodes Woman with a thing for bars, since apparently her mother once screwed Russell Thorpe on the one at the Peninsula Hotel. Lily gets him to move the subject to whether or not she would ever cheat on Rufus, and Lily admits that they have a sham marriage and that she is his beard and that he's been sleeping with Scott Weiland this entire time, I mean she doesn't say this but it's in the air, and that she's only sticking with her fifth husband because of the PR they're dealing with right now, what with her daughter constantly ruining parties and scaring off potential buyers and her son getting punched by her all the time and raping all those people every day.
But what's really going on with all this, beyond mind games for mind games's sake, is that Chuck is stealing documents off Russell's computer using the Captain's info from last week, which gives this whole scene a fun little urgency; around the time Russell's sort of asking her to divorce Rufus and marry him, she gets the all-clear from Charles and runs off again. You can never be too sure you've fooled Russell, but it looks pretty promising at this point.