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1.
A word that simultaneously expresses both joy and condolence for the fortunes of another, "congratusorry" should be directed towards an individual when they suffer disappointing results from a situation that typically concludes with a positive outcome. A question mark after congratusorry isn't entirely necessary, but can prove helpful in ambiguous situations. (Also see "seizing defeat from the jaws of victory".)
Jim: My wife just had a baby.
Bob: That's wonderful...
Jim: It wasn't mine.
Bob: Oh... congratusorry?
by Le_Sigh June 18, 2007