Guest Stars Kyla Matthews as Ruby Gillis Lia Pappas-Kemps as Jane Andrews Jacob Ursomarzo as Moody Spurgeon Miranda McKeon as Josie Pye Jacob Horsley as Charlie Sloane Glenna Walters as Tillie Boulter Christian Martyn as Billy Andrews Kyle Meagher as Paul #1 Daimen Landori-Hoffman as Paul #2 Ella Jonas Farlinger as Prissy Andrews Brian Tree as Minister Janet Porter as Mrs. Andrews Stephen Tracey as Mr. Phillips