| 100% | ANYDAY | 6 | Regardless of the date |
| 69% | ATANYCOST | 9 | Regardless of the consequences |
| 69% | ATALLCOSTS | 10 | Regardless of the results |
| 69% | ATANYCOST | 9 | Regardless of the price |
| 69% | ATALLCOSTS | 10 | Regardless of the repercussions |
| 69% | WINORLOSE | 9 | Regardless of the outcome |
| 69% | COMEWHATMAY | 11 | Regardless of the consequences |
| 67% | ALTHO | 5 | Regardless of the fact that, briefly |
| 63% | RAINORSHINE | 11 | “This event is happening regardless of the weather” |
| 62% | CIRCA | 5 | Around the date of |
| 61% | NERD | 4 | User of the dating site www.matchgeeks.com, perhaps |
| 61% | EARLY | 5 | Ahead of the due date |
| 58% | ASIA | 4 | It's west of the International Date Line |
| 58% | ATTU | 4 | Westernmost land east of the International Date Line |
| 58% | MEN | 3 | Majority of the contestants on "The Dating Game" |
| 57% | FOURTH | 6 | The United States independence date, __ of July |
| 57% | RENEW | 5 | Extend the due date of |
| 56% | WINORLOSE | 9 | *"Regardless of the outcome ..." |
| 55% | CARD | 4 | Check the birth date of, say |
| 55% | OBS | 3 | Out of date, in the OED |
| 55% | DDAY | 4 | Common name of the pivotal WWII date June 6, 1944: Hyph. |
| 55% | SAINT | 5 | With 51-Across, early adopter of the A.D. dating method |
| 55% | AROD | 4 | Nickname of the former Yankee who once dated J.Lo: Hyph. |
| 54% | OAKAPPLE | 8 | __ Day, date celebrates the Restoration of 1660 |
| 54% | SUPERBOWL | 9 | Feb. 7, 2010, the date of this event's number 55-Across |
| 54% | AROD | 4 | Nickname of the retired Yankees player who's dating J.Lo: Hyph. |
| 53% | MAYISEEYOUAGAIN | 15 | Question at the end of a pleasant date |
| 53% | IDES | 4 | Middle date of the Roman months |
| 53% | LOSE | 4 | "Win or ___ ..." ("Regardless of the outcome ...") |
| 53% | KILLERS | 7 | "___ of the Flower Moon," film starring Leonardo DiCaprio whose release date is in 2023 |