| Answer | Crossword Clue |
|---|---|
| SILLYME | "I should've known better" |
| DUH | "I should've known that!" |
| AIMEE | "I Should've Known" singer Mann |
| DOT | "I should've known, .. ..." (Aimee Mann) |
| DUH | "I should've seen that!" |
| DUH | "I should've thought of that!" |
| BRR | "I should've brought a sweater" |
| BRR | "I should've worn a coat!" |
