| 100% | DEAR | 4 | Starting word in a letter to someone you love |
| 52% | DEAR | 4 | First word in a letter to Santa |
| 42% | ONCEUPONATIME | 13 | Words you would use to start a fairy tale?: 4 wds. |
| 42% | SENT | 4 | Posted a letter to someone |
| 42% | DEAR | 4 | First word in a letter, often |
| 42% | LIST | 4 | Enclosure in a letter to Santa |
| 41% | KEY | 3 | What you turn in the ignition switch to start a car |
| 41% | LETMEGUESS | 10 | Words from someone with a good idea of what you’re about to say |
| 40% | AMOR | 4 | Word in a Spanish love song |
| 40% | AMO | 3 | Word in a Latin love poem |
| 40% | AMO | 3 | Word in a Spanish love poem |
| 40% | DEAR | 4 | Common word to start a letter with |
| 40% | PERHAPS | 7 | Repeated word in a Doris Day song with the lyrics "If you can't make your mind up / We'll never get started" |
| 39% | ISENT | 5 | "___ a Letter to My Love" (Simone Signoret film) |
| 38% | ILLGETIT | 8 | Words in response to a doorbell |
| 38% | DEAR | 4 | Word that a letter might start with |
| 38% | AMOR | 4 | Word in many a Spanish love song |
| 38% | KISS | 4 | "X," in a love letter |
| 38% | OOO | 3 | Hugs, in a love letter |
| 38% | KISS | 4 | X, in a love letter |
| 38% | BRO | 3 | A term used to call someone you probably hear in a frat |
| 37% | HARDEST | 7 | "Sorry Seems to Be the ___ Word," a hit by Elton John, that was covered by Blue in "One Love" |
| 37% | YEAH | 4 | Repeated word in "She Loves You" |
| 37% | DEARANN | 7 | Start of a letter to Landers |
| 37% | AFFIX | 5 | Add-on to the start or end of a word stem (as in 17-, 25-, 35-, 49- and 57-Across) |
| 37% | NUTSHELL | 8 | In a __ means to be explained in few words |
| 37% | XOO | 3 | Kiss and hugs, in a love letter |
| 37% | BEQUEATH | 8 | Leave something to someone in a will |
| 37% | ANAGRAM | 7 | Transposing letters to make a new word |
| 37% | DEAREST | 7 | Start of a love letter |