In the last decade alone, the world has changed in seismic ways as marriage equality has been ruled on by the supreme court, social justice issues such as #metoo and BlackLivesMatter have arisen, and issues of immigration and deportation have come to the forefront of politics across the globe. Thus, there is a need for an updated text that shares strategies for combining canonical and young adult literature that reflects the changes society has – and continues to - experience. The purpose of our collection is to offer secondary (6-12) teachers engaging ideas and approaches for pairing young adult and canonical novels to provide unique examinations of topics that teaching either text in isolation could not afford. Our collection does not center canonical texts and most chapters show how both texts complement each other rather than the young adult text being only an extension of the canonical. Within each volume, the chapters are organized chronologically according to the publication date of the canonical text. The pairings offered in this collection allow for comparisons in some cases, for extensions in others, and for critique in all. Volume 2 covers The Canterbury Tales (1392) through Fallen Angels (1988).