"One-on-One 101" confronts longstanding and often hidden roadblocks to successfully getting through to students. Modern education must address how to positively inspire students on a One-on-One level, as the system pivots towards emerging methods, such as "flipped" and blended learning, homeschooling, independent study schools, and One-on-One academies. Traditional classroom models must also cultivate positive One-on-One dynamics as well, as they are at the heart of the teacher-student bond. We are in dire need of a complete field manual for how to habitually create a transcendent One-on-One relationship between a teacher and student.