| Wretched | Pitiable | Dejected |
| Woeful | Pessimistic | Dark |
| Woebegone | Pathetic | Cruel |
| Wistful | Painful | Crestfallen |
| Weighty | Oppressive | Cheerless |
| Upsetting | Nasty | Bleak |
| Upset | Moving | Bitter |
| Unhappy | Mournful | Bad |
| Unfortunate | Morose | Appalling |
| Unbearable | Morbid | Aggrieved |
| Troubled | Moody | Forlorn |
| Tragic | Miserable | Dreary |
| Tough | Melancholy | Downhearted |
| Tearful | Melancholic | Downcast |
| Taxing | Lugubrious | Down |
| Sorry | Low-spirited | Dolorous |
| Sorrowful | Low | Doleful |
| Sore | Leaden | Disturbing |
| Sombre | Lamentable | Distressing |
| Somber | Lachrymose | Distressed |
| Sluggish | Joyless | Dispiriting |
| Shabby | Inconsolable | Dispirited |
| Severe | Heartsick | Dismal |
| Serious | Heartrending | Disheartening |
| Sensitive | Heartbroken | Disheartened |
| Rough | Heartbreaking | Disconsolate |
| Regrettable | Grim | Disastrous |
| Profound | Grievous | Dire |
| Poor | Grieved | Difficult |
| Ponderous | Grave | Despondent |
| Poignant | Glum | Desolate |
| Plaintive | Gloomy | Depressing |
| Pitiful | Funereal | Depressed |
