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Answer:
SADDEST
Possible questions:
Most pathetic
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Most mournful
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Most morose
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Most blue
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Most miserable
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Most downcast
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Most down
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Word for "It might have been!"
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Superlatively sorrowful
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Most woeful
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Most forlorn
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Most dolorous
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Most deplorable
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Lower than the rest
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Least happy
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Furthest down in the dumps
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Bummed to the max
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