Group dancing! Blair agrees to go to Debutante Ball with Nate as friends, rekindling his feelings. Nate"s suspicions that she"s seeing somebody force Chuck to pull Carter Baizen (the Not-So-Sexy Hobbit) into their love triangle, but it backfires when Blair is impressed with Nate"s caveman behavior, and they end up getting back together right in front of Chuck"s eyes. Thus burned by both his girlfriends, Chuck leaves town for parts unknown. Come back, Chuck! XOXO!
The Ball conflicts with Alison"s art opening, but both Humphrey kids eventually end up going anyway. Jenny"s horrific whining and inability to finesse the situation breaks her mom"s heart, and makes her look like a total jerk. Meanwhile, the whole Dan/Serena situation is all very complicated with a lot of moving parts, and everything is louder than everything else: Serena doesn"t even want to go to the Ball, which mother Lily supports, but then grandmother Cece shows up and starts throwing around the fake cancer of manipulation. When Cece delivers a truly awesome, bitchy speech to Dan about his innate inability to fit into the UES, and tries to buy him off, Dan tries to get Serena to see how hardcore her grandmother really is. This goes poorly; Serena is escorted by Carter the Hobbit. Once Rufus learns this exact same shit is the reason Lily left him long ago, he gives Dan a Humphrey Men speech that"s actually worthwhile, and they unite to resist Cece. Lily then gives Dan an awesome speech of her own about how cool he and Serena have turned out to be, separately and together, and everybody melts; even cold Grandma Cece. Who, it turns out, has secret cancer after all. Lily watches Dan and Serena"s romance bloom, and Rufus calls her about the long-ago bribing, and they both get misty.
Final score: Blair"s back with Nate, Chuck has vanished, Serena and Dan have Lily"s blessing, Alison is the first person to notice that Jenny is becoming a psycho killer, and Lily and Rufus realize that their ill-starred love might have a few stars left in it after all. On the 19th, Dan and Serena finally do it, and Harold Waldorf bears tidings of gay joy, and a cute little present named Roman.