Ben and Serena have a whole Aaron Rose conversation that on the outside is about how dumb and clichéd Valentine's Day is, but on the inside is about the gaping black hole of need that informs Serena's relationships. "The wolves won't come for you until I have entirely consumed your soul, Ben!" In pursuit of this obvious endpoint, Serena asks Ben about his job prospects and then before he can say "cater waiter," she fills in the blanks with all kinds of shit that makes him feel bad. "Hedge fund manager? Airline pilot? Astronaut? Prime Minister of England?" Ben's like, "All of those, actually. It's been a good day." Serena's so happy for him, because he really needed a win.
So since she was just at the brunch with Raina, and now she's meeting Raina at Ralph Lauren, one might wonder why Serena was just alone talking to Ben on the street for that entire scene. It's a fruitless question, but I will tell you: They left PRADA together, and Raina hailed them a cab, but Serena wandered off into the middle of the street, somehow tangled in her tights. Raina, she's very forthright and efficient as we know, so she took one look at that mess and called out, "I'll just meet you there!" And Serena, muffled, was all, "Who said that!? Why's it so dark inside my tights?" Carter Baizen gently took her by the hand and led her to Ralph Lauren, and by the time she could see again he was gone, a sexy wee shadow.
The Archibalds -- to whom Chuck refers, deliciously, as the collective "Archibalds" -- show up with bad scary tidings: Apparently Russell's agreement to this ridiculous secret party was a sham, and in fact he's still interested not only in cutting Chuck out of Bass Ind., but still chopping it up into bits and setting the bits on fire and trampling the bits. Chuck makes up a new, nonsensical aphorism -- some shit about how the Captain would rather "grind an ax across his knuckles" than help him, which is not a saying -- and then these three (the disgraced financier, the billionaire roué, the beautifully empty rentboy) decide that they've deduced something or other: This is still about Bart.
Raina, she's very honest, and she explains that she was only fucking Chuck because it was fun and that she knew he was after her aid with the company, but then it changed into true love. "I want to find an amazing dress," Raina says in the middle of Ralph Lauren, "And totally take his breath away." Because she is from Chicago, Raina has never been shopping before, so Serena helps her out with that.