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All answers having "Hurtful" as clue:

3 Character Answers:

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BAD



4 Character Answers:

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MEAN



5 Character Answers:

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PUMPS



7 Character Answers:

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ABUSIVE

CUTTING

MALEFIC



9 Character Answers:

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INJURIOUS



10 Character Answers:

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PERNICIOUS



11 Character Answers:

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DELETERIOUS

DELITERIOUS