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There are 19 clues with the answer 'GLOOMYGUS'
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CLUE
1.
Dour sort
2.
Guy who's always frowning and moping: 2 wds.
3.
Glass-half-empty kind of guy
4.
Debbie Downer's partner?
5.
*Morose fellow
6.
Mr. Worrywart?
7.
Habitually sullen sort
8.
Worrywart
9.
Sourpuss
10.
Pessimistic person
11.
Pessimist
12.
Optimist's opposite
13.
Doomsayer
14.
Morose fellow (2 wds.)
15.
*Glass-half-empty sort (... letters 7-5)
16.
Glass-half-empty sort (...letters 7-5)
17.
Member of the blue man group?
18.
One with an Eeyore-like outlook
19.
Glass-half-empty kind of guy (6,3)