| 100% | SMALL | 5 | Taylor ___, Vermont's first openly transgender legislator |
| 48% | STU | 3 | Rasmussen who was the first openly transgender mayor in the U.S. |
| 44% | ISIS | 4 | Actress and activist King who was the first openly transgender competitor on “America’s Next Top Model” |
| 44% | LAYSHIA | 7 | ___ Clarendon, first openly transgender W.N.B.A. player |
| 44% | TEC | 3 | Religious org. of Rev. Cameron Partridge, first openly transgender priest to preach at Washington's Natl. Cathedral (2014) |
| 43% | VICTORIASSECRET | 15 | Retailer that hired its first openly transgender model in 2019 |
| 40% | KIMPETRAS | 9 | First openly transgender woman to have a No. 1 song on the Billboard Hot 100 chart |
| 40% | LIA | 3 | ___ Thomas, first openly transgender athlete to win an NCAA Division I national championship (swimming) |
| 38% | INES | 4 | ___ Rau (first openly transgender Playboy Playmate) |
| 37% | BARNEYFRANK | 11 | First openly gay U.S. congressman |
| 36% | LEO | 3 | ___ Varadkar, Ireland's first openly gay Prime Minister |
| 36% | OWEN | 4 | ___ Hurcum, the world's first openly nonbinary mayor |
| 36% | DANICAROEM | 10 | America's first openly trans elected state official |
| 34% | MILK | 4 | Harvey who was California's first openly gay elected official |
| 34% | MILK | 4 | Harvey who was California's first openly gay public official |
| 33% | OURSONG | 7 | Taylor Swift's first #1 country hit, 2007 |
| 33% | LOVESTORY | 9 | Taylor Swift's first single from Fearless album |
| 33% | LOVER | 5 | Taylor Swift’s first album after leaving Big Machine Records |
| 29% | IGOR | 4 | ___ Benevenuto, first openly gay FIFA ref |
| 28% | ANA | 3 | ___ Brnabic, first openly gay Prime Minister of Serbia |
| 27% | STRATEGIC | 9 | First S in OSS, precursor of CIA |
| 27% | MTSNOW | 6 | Ski resort in S. Vermont |
| 26% | USCG | 4 | S O S first responders |
| 26% | SOVIET | 6 | The first S in USSR |
| 26% | RACHELMADDOW | 12 | First openly lesbian anchor to host a major prime-time news program |
| 26% | MLK | 3 | First president of the S.C.L.C. |
| 26% | OUR | 3 | "___ Song" (Taylor Swift's first #1 hit) |
| 25% | TROYAL | 6 | First name of Garth Brooks, an anagram of Taylor |
| 25% | HIRAM | 5 | Ulysses S. Grant's real first name |
| 25% | HIRAM | 5 | U. S. Grant's given first name |