| Maximally upsetting news ultimately set dad off |
The Times Cryptic |
16 Aug 2025 |
| Describing total mess essentially, good person is most sorry |
The Telegraph Toughie |
05 Jun 2025 |
| Most down in the dumps |
Commuter |
02 Jun 2025 |
| Most low diamonds singer keeps with spades out at last |
The Telegraph Toughie |
23 May 2025 |
| Most tragic |
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| Mopiest |
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| Most tragic part of Mossad destruction (7) |
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| Most miserable, unhappiest |
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| Most unhappy dad's set to change (7) |
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| Most doleful |
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| Most upsetting (7) |
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| Dead drunk in South Street and in the worst of spirits (7) |
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| Most sorrowful |
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| Dad's set out to be most unhappy (7) |
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| Most blue |
LA Times Daily |
30 Jul 2023 |
| Dad sets out to be bluest |
The Telegraph Cryptic |
02 Mar 2023 |
| Most pathetic |
Wall Street Journal |
27 Oct 2022 |
| Most forlorn |
Universal |
25 Jan 2022 |
| Maximally low |
The Washington Post Sunday |
12 Dec 2021 |
| Farthest down? |
New York Times |
31 Oct 2021 |
| To say more in French is, after a touch of Spanish, most regrettable |
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| Most regrettable |
The Washington Post Sunday |
18 Apr 2021 |
| Unhappiest |
The Telegraph Quick |
15 Oct 2019 |
| Most melancholy |
Newsday |
08 Feb 2019 |
| Singular art including most blue |
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| Most unfortunate |
Newsday |
02 Dec 2018 |
| Most morose |
Newsday |
15 Apr 2018 |
| Most blue films, in the end, set dad off |
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| Most mournful |
The Washington Post |
05 Dec 2017 |
| Most mournful |
LA Times Daily |
05 Dec 2017 |
| As low as can be |
Newsday |
21 Oct 2017 |
| Most blue West End seats not left first |
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| Most unhappy when daughters break new seats |
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| Most mournful |
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| Most downcast |
The Washington Post |
07 Jul 2016 |
| Superlatively sorrowful |
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| Most morose |
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| Least happy |
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| Most pathetic |
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| Furthest down in the dumps |
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| Most blue |
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| Most pitiful |
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| Most mournful |
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| Most woeful |
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| Bummed to the max |
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| "The ___ are these, 'It might have been'" (Whittier) |
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| Most down |
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| "... the ___ are these: 'It might have been!'": Whittier |
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| Most forlorn |
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| Least cheerful |
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| Lower than the rest |
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| Most unhappy |
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| Most long-faced |
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| Most pathetic |
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| Least happy |
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| Least light-hearted |
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| Most deplorable |
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| Most downcast |
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| Most dolorous |
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| Most morose |
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| Word for "It might have been!" |
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| Most miserable |
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| Most pathetic. |
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| Most deplorable. |
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