| 100% | SORRYIASKED | 11 | "Shouldn't have brought that up" |
| 59% | OOPS | 4 | "I shouldn't have done that" |
| 59% | BADANSWER | 9 | "You shouldn't have said that!" |
| 59% | TSKTSK | 6 | "You shouldn't have done that" |
| 59% | TSK | 3 | "You shouldn't have done that!" |
| 59% | OOPS | 4 | "I shouldn't have done that!" |
| 58% | TSK | 3 | ''You shouldn't have done that!'' |
| 57% | MYBAD | 5 | "I shouldn't have done that": 2 wds. |
| 56% | OOPS | 4 | "Guess I shouldn't have done that" |
| 53% | NOTCOOL | 7 | "You really shouldn't have done that, bruh" (2 wds.) |
| 52% | MEANDMYBIGMOUTH | 15 | "Oh, no! I shouldn't have told you that!" |
| 51% | BADMOVE | 7 | "Shouldn't have done that!" |
| 51% | OOPS | 4 | "Shouldn't have dropped that" |
| 51% | REMORSE | 7 | "Shouldn't have bought that" feeling |
| 49% | PREVENTABLE | 11 | Like something that really shouldn't have happened |
| 48% | ARAL | 4 | Sea that has split up |
| 48% | ZIPPING | 7 | Doing up a coat that doesn't have buttons |
| 48% | RETIREES | 8 | Those who have given up their working lives |
| 47% | REAR | 4 | Bring up ... or something that might be brought up |
| 47% | SITARS | 6 | Instruments that have up to 21 strings |
| 47% | CABOOSE | 7 | Train car that brings up the rear |
| 47% | YOYOS | 5 | Toys that have their ups and downs |
| 47% | NRA | 3 | Org. that has people up in arms? |
| 47% | SCIMITAR | 8 | Mark brings up fellow having one weapon |
| 47% | OTIS | 4 | Name that has its ups and downs |
| 47% | OTIS | 4 | Company that has its ups and downs |
| 46% | PSALM | 5 | Song that can have up to 176 verses |
| 45% | RAISING | 7 | Bringing up, as a child that sounds like a dried fruit |
| 45% | JELLICLES | 9 | T S Eliot's cats that meet up at a ball |
| 45% | SUCTION | 7 | Power that a vacuum has to lift objects up |