[12] As the youngest of at least ten surviving children[6] (including an oldest brother, Oliver, who had enlisted in the Massachusetts militia and died sometime in August of 1776),[6] Bryant was often treated with "affectionate indulgence"[8] by her older siblings, who also instilled in her a love for poetry that would stay with her throughout her life.

[14] During this time, she formed intimate relationships with several of her fellow teachers,[15] including most notably Lydia Richards, with whom Bryant exchanged a number of poems containing somewhat erotic imagery.

[18] Their community, including their relatives, accepted them as a married couple after many years of consistency and courage from both Charity and Sylvia.

Drake discussed their relationship in her diaries: Tuesday- 3 [July]—31 years since I left my mother’s house and commenced serving in company with Dear Miss B.

Sin mars all earthly bliss, and no common sinner have I been, but God has spared my life, given me every thing I would enjoy and now I have a space, if I improve it, to exercise true penitence.

I would tell you how, in their youthful days, they took each other as companions for life, and how this union, no less sacred to them than the tie of marriage, has subsisted, in uninterrupted harmony, for more than forty years.

Charity wrote many poems throughout her lifetime, which she later ordered to be burned after her passing, but the few that remain are mostly written to Sylvia, expressing love and the need to protect her always.

[31] Bryant and Drake are buried together under a shared headstone at Weybridge Hill Cemetery, Addison County, Vermont.