| 100% | DATES | 5 | "50 First ___" (Sandler/Barrymore romcom) |
| 84% | DATES | 5 | "50 First ___" (Drew Barrymore romcom) |
| 78% | DATES | 5 | " 50 First ___" (Adam Sandler movie) |
| 78% | DATES | 5 | "50 First ___," 2004 romantic comedy film starring Adam Sandler and Drew Barrymore |
| 65% | DREW | 4 | ___ Barrymore and Adam Sandler, "50 First Dates" actors who have starred in multiple rom-coms together |
| 63% | DREW | 4 | "50 First Dates" actress Barrymore |
| 63% | DREW | 4 | "50 First Dates" star, Barrymore |
| 63% | DREW | 4 | "50 First Dates" actress ___ Barrymore |
| 63% | DATES | 5 | "50 First ___" (Drew Barrymore movie) |
| 62% | DATES | 5 | "50 First ___" (Drew Barrymore rom-com) |
| 56% | MEETCUTE | 8 | First encounter in a romcom |
| 55% | DREW | 4 | Actress ___ Barrymore from "50 First Dates" |
| 55% | ADAM | 4 | Actor Sandler of "50 First Dates" |
| 53% | MEETCUTE | 8 | Romcom first encounter |
| 51% | DEL | 3 | First of 50: Abbr. |
| 49% | MEETCUTE | 8 | First encounter in a romcom (Hyph.) |
| 48% | ADLAI | 5 | First name in 50's politics |
| 48% | DESI | 4 | First name in 50's TV |
| 48% | PAT | 3 | First Family member, 50 years ago |
| 47% | SANDLER | 7 | Actor Adam known for Happy Gilmore, 50 First Dates |
| 47% | SANDLER | 7 | Adam, star of 50 First Dates and The Waterboy |
| 46% | FIRST | 5 | "50 ___ Dates," 2004 rom-com starring Adam Sandler and Drew Barrymore that was shot in Hawaii |
| 46% | BARRYMORE | 9 | Drew, actress who went on 50 First Dates in 2004 |
| 46% | BARRYMORE | 9 | She starred in 50 First Dates and Charlie's Angels |
| 46% | SNL | 3 | First show to win 50 Emmys, in brief |
| 45% | THEGNIDDEWSINGER | 16 | 1998 Adam Sandler/Drew Barrymore rom-com |
| 43% | SAGUAROS | 8 | They first bloom when 50-75 years old |
| 42% | MUSIC | 5 | & 2D 2007 romcom starring Hugh Grant and Drew Barrymore |
| 42% | SIGEP | 5 | First college frat to charter a chapter in all 50 states |