Among the numerous letter-writing manuals which were printed in eighteenth-century Britain, a few were authored by such famous novelists as Samuel Richardson or Daniel Defoe. The present volume is a first-time edition of an autograph manual devised by William Gilpin, commonly known as one of the theoreticians of the picturesque, which he intended either for individual use in the schools he was teaching or for publication. The manual was exclusively devised for boys and men. Although its primary purpose was to provide models of letters on various occasions (at school, in apprenticeship, in debts, in mourning), its content is also partly fictional, since several groups of letters provide short stories about the lives of young soldiers writing home, reformed rakes making a fortune in India or fathers trying to correct their sons’ misdemeanours. The whole tone is highly moral, since the manual was also conceived as a work of edification. As such, it is an excellent counterpart to the correspondence which William Gilpin exchanged with his grandson, William Writes to William: The Correspondence of William Gilpin (1724–1804) and his Grandson William (1789–1811) (Cambridge Scholars Publishing, 2014). The manual is presented with an introduction, notes, index and appendix of a list of eighteenth-century letter-writing manuals, focusing on the issues of sources, society and epistolary writing.