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There are 29 clues with the answer 'ITSSAD'
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CLUE
1.
"What a disgrace"
2.
"What a shame..."
3.
"So tragic"
4.
"So unfortunate!"
5.
"How unfortunate"
6.
"Alas ..."
7.
"How tragic"
8.
"Alas . . ."
9.
"How unfortunate ..."
10.
"Such a shame"
11.
'What a shame'
12.
"What a shame"
13.
"What a shame!"
14.
"What a pity"
15.
"That's a shame"
16.
"Alas..."
17.
"So unfortunate . . ."
18.
"So unfortunate ..."
19.
Response to something that makes you go ☹: 2 wds.
20.
"What a shame..." equivalent spelled using only the letters in "staid": 2 wds.
21.
Warning when recommending a tearjerker
22.
"You hate to see that sort of thing"
23.
"How tragic": 2 wds.
24.
"How awful": 2 wds.
25.
"How regrettable..."
26.
"Here's bad news"
27.
"Such a shame . . ."
28.
Pitying statement
29.
"I feel so bad for them"