- - Least happy
- - Least light-hearted
- - Least cheerful
- - Most unhappy dad's set to change
- - dad sets out to be most unfortunate
- - not the happiest of dads set out
- - Most unhappy, couple of dukes in awful seats
- - Most sorrowful
- - maximally low
- - Count up Es in street — most distressing!
- - To say more in French is, after a touch of Spanish, most regrettable
- - Most doleful
- - Maximally melancholy
- - Most depressing
- - Unhappiest
- - Most unfortunate
- - Most mournful
- - As low as can be
- - Superlatively sorrowful
- - Furthest down in the dumps
- - Most pitiful
- - Most woeful
- - Bummed to the max
- - "The ...... are these, 'It might have been'" (Whittier)
- - Most forlorn
- - Lower than the rest
- - Most unhappy
- - Most long-faced
- - Most deplorable
- - Most dolorous
- - Word for "It might have been!"
- - Most pathetic
- - Most miserable
- - Most downcast
- - Most blue?
- - Most melancholy
- - Most down
- - Most morose
- - Most depressed
- - Farthest down
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