| 100% | DEMI | 4 | ___ Lovato, singer of "Give Your Heart A Break" |
| 85% | DEMI | 4 | "Give Your Heart a Break" singer Lovato |
| 81% | DEMI | 4 | Singer Lovato who sang "Give Your Heart a Break" |
| 65% | DEMI | 4 | Lovato with the hit "Give Your Heart a Break" |
| 59% | LOVATO | 6 | Demi with the 2012 hit "Give Your Heart a Break" |
| 49% | JOHNMAYER | 9 | Singer of Your Body Is a Wonderland |
| 47% | MIND | 4 | Give a piece of your ___ (berate) |
| 45% | LUKECOMBS | 9 | Singer of the 2019 country hit "Beer Never Broke My Heart": 2 wds. |
| 45% | TITHE | 5 | Give 1/10 of your money to a church |
| 45% | JLO | 3 | Singer of a "This Land Is Your Land" medley at the Biden inauguration, familiarly |
| 44% | ROB | 3 | "This Is How a Heart Breaks" singer ___ Thomas |
| 44% | TEDDYTOEDDY | 11 | Toy bear given by a fan of singer Arnold? |
| 42% | GRACE | 5 | "___ of My Heart," movie in which Ileana Douglas plays a singer-songwriter |
| 42% | TONI | 4 | ___ Braxton, singer of "Un-Break My Heart" |
| 42% | HANDYMAN | 8 | Guy to see "if your broken heart needs repair," in a song |
| 41% | TONI | 4 | Singer Braxton of "Un-Break My Heart" |
| 39% | NOD | 3 | Give your head a shake |
| 39% | WREN | 4 | Singer of a complex song |
| 39% | UNTO | 4 | "___ a broken heart": Dickinson |
| 38% | SIA | 3 | Singer of the hit "Elastic Heart" |
| 38% | BEAT | 4 | Your heart has a rhythmic one |
| 38% | MONODIST | 8 | Singer of a single melodic line |
| 38% | HEAL | 4 | Mend a broken heart? |
| 38% | RAT | 3 | Singer, of a sort |
| 38% | DIRTYRAT | 8 | Singer, of a sort |
| 38% | THEXFACTOR | 10 | Singer Demi Lovato was a judge in the second and third season of this music-based reality show: 3 wds. |
| 38% | SIA | 3 | Singer of "Elastic Heart" and "The Greatest" |
| 38% | ERNIE | 5 | Singer of a famous bath time song |
| 38% | ADELE | 5 | "Cry Your Heart Out" singer |
| 38% | UNTO | 4 | "___ a broken heart" (Emily Dickinson poem) |