| piteous(sad, painful, distressing, sorry, mournful) |
| pitiable(adjective, sad, unhappy, unpleasant, woe) |
| pitiful(adjective, sad, unhappy, unpleasant, woe) |
| plaintive(sad, painful, distressing, sorry, mournful) |
| poor(adjective, sad, unhappy, unpleasant, woe) |
| poor dear(adjective, sad, unhappy, unpleasant, woe) |
| poor fellow(adjective, sad, unhappy, unpleasant, woe) |
| punk(adjective, sad, unhappy, unpleasant, woe) |
| rueful(sad, painful, distressing, sorry, mournful) |
| screwed-up(adjective, sad, unhappy, unpleasant, woe) |
| sick |
| singing the blues(expression, sad, painful, distressing, sorry) |
| sinister(adjective, sad, unhappy, unpleasant, woe) |
| somber |
| sow(adjective, sad, unhappy, unpleasant, woe) |
| star-crossed(adjective, sad, unhappy, unpleasant, woe) |
| star crossed(adjective, sad, unhappy, unpleasant, woe) |
| sticky-fingered(adjective, sad, unhappy, unpleasant, woe) |
| tacky(adjective, sad, unhappy, unpleasant, woe) |
| tear-jerking(sad, painful, distressing, sorry, mournful) |