| 100% | MORAN | 5 | Bugs whose rival gunned down 7 members of his gang in 1929's Saint Valentine's Day Massacre |
| 23% | ROSE | 4 | One of twelve in a Valentine’s Day bouquet |
| 22% | KEN | 3 | He reunited with his fictional ex on Valentine's Day in 2011 |
| 22% | JASONROBARDS | 12 | Actor who played 15-Across in the 1967 film "The St. Valentine's Day Massacre": 2 wds. |
| 22% | BRIGAND | 7 | Member of a gang that robs people in forests |
| 22% | HEELS | 5 | "Head over ___," phrase for a way of falling in love this Valentine's Day |
| 22% | MICHAELBOLTON | 13 | Singer whose "Big, Sexy Valentine's Day Special" premiered on Netflix in 2017 (2 wds.) |
| 21% | RYAN | 4 | Actress Meg of "Sleepless in Seattle," who got married to Dennis Quaid on Valentine's Day |
| 21% | ILUVU | 5 | Start of the song title in the 25 Across clue, but imagine it on Valentine's Day candy |
| 20% | ALCAPONE | 8 | St. Valentine's Day Massacre organizer |
| 20% | ABBA | 4 | Band whose members received one of Sweden's highest civilian honors in May |
| 20% | PINKLADY | 8 | Rosy apple; member of the girl gang in Grease |
| 20% | DURER | 5 | Albrecht —, German Renaissance painter and theorist whose engravings include 1514's Saint Jerome in His Study |
| 20% | HASH | 4 | Something you can buy at any time of day in Frank's Diner down on the corner |
| 20% | ROSAS | 5 | Valentine's Day flowers, in Spain |
| 20% | ADDAMS | 6 | Surname of a family whose members can be found in nine rows in this puzzle ... and whose names contain circled letters that, reading down, spell a word describing them |
| 19% | CUPID | 5 | Symbol of Valentine's Day |
| 19% | HEART | 5 | Symbol of Valentine's Day |
| 19% | BURNINGDESIRE | 13 | Lana Del Rey's song from her third EP, "Paradise" whose music video was released on Valentine's Day in 2013: 2 wds. |
| 19% | NERVO | 5 | Jimmy —, member of the Crazy Gang whose comedy partner was Teddy Knox |
| 19% | CHARLIEHUSTLE | 13 | Nickname of 15-Across in his playing days: 2 wds. |
| 19% | POSSES | 6 | Rival rap groups in the early days of hip-hop |
| 19% | MOM | 3 | Family member whose special day is in May |
| 19% | ADA | 3 | Org. whose members look down in the mouth? |
| 19% | FEBRUARY | 8 | Valentine's Day is celebrated in this month |
| 19% | TROMP | 5 | Noted percussion competition whose Repertoire Days were at Rochester's Eastman School of Music in November 2019 |
| 19% | RED | 3 | Signature color of Valentine's Day |
| 19% | DRAGOBETE | 9 | Romanian equivalent of Valentine's Day |
| 19% | BUD | 3 | & 9A Member of comedy team the Crazy Gang whose partner was Chesney Allen |
| 19% | FLANAGAN | 8 | Bud —, member of comedy team the Crazy Gang whose partner was Chesney Allen |