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Answer:
SADDER
Possible Questions:
More melancholy
More doleful
Less happy
More down
Wiser, perhaps
Wiser partner?
Not so sunny
More depressing
More melancholic
More blue
Less upbeat
Not as impressive
Not as fortunate
More downcast
More deplorable
More crushed
Lower in spirits
Further down in the dumps
Even more pathetic
Deeper blue?
Bluer
"___ but wiser"