Blair thinks Cyrus may have discovered a loophole in her prenup; Georgina and Chuck embark on a scheme that has surprising results; a crisis brings William van der Woodsen (Billy Baldwin) back to the city.
Dan is honored when he learns Upright Citizen's Brigade is performing excerpts of his book; Blair tries to save her friendship with Serena; Ivy winds up on a collision course with the van der Woodsens.
Chuck wants to express his gratitude to Jack; Dan and Blair encounter unexpected obstacles as they try to consummate their new relationship; Ivy finds an ally; Nate seeks an investor.
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