The first generation of young people following the Revolution were full of hope and anxious to stretch their wings through education and adventure. We know the Dering family's activities because the father Sylvester who saved his letters also wrote of family affairs to his son Nicoll who also saved his letters. These are stories of nine young people (all of whom are related, save one) told through their letters. Abraham Tuthill aspired to be a portrait painter; Frances Dering and Frances Sage would forge a deep bond; Sisters Catherine and Frances Huntington shared a school in New York; Charles Thomas Dering invested in the Union, a whaling ship; Mary L'Hommedieu suffered financially as a child; Margaret Dering married a man who was disowned by his father for seeking a career as a preacher; Eliza Gardiner found comfort in a kind man.