The great medieval thinker Peter Abelard is renowned for his uncompromising and radical approach to ethics and theology, a towering public figure in twelfth-century schools and monasticism. The Repentant Abelard argues, however, that later in his life, Abelard's thoughts turned again towards his own family, and it explores the works he wrote at this time for his former wife Heloise and son Astralabe. These include six laments (Planctus) for Heloise written in the voices of Old Testament figures, works of extraordinary poetry, resonant with love, sorrow, and despair. For his son he wrote a long poem of didactic advice (Carmen ad Astralabium) in which he summarized decades of his controversial ethical and theological ideas. This book offers a new Latin edition of these texts complete with first-time full English translation and comprehensive notes. The works are introduced by thematic, stylistic, and reception studies which reveal how powerful and unique these texts are within Medieval Latin literature. As such, they stand as truly personal gifts from Abelard to his family.