I am proposing to undertake research supporting a moral case for play in Jewish day schools. With lower school families concerned about the academic viability of Jewish day schools and with upper school students weighed down by college admissions pressures, anxiety and depression (the subject for a recent New York Times Magazine cover article), a turn toward play could help students at Jewish day schools feel re-engaged, reinvigorated and lighter on their feet. As Stuart Brown writes, “The opposite of play is not work; it is depression.” Students at the school where I work undertook a self-administered questionnaire of character strengths through the viacharacter.org website, and they scored high in character strengths of gratitude, love, teamwork and humor and low in spirituality, self-regulation, humility and honesty. The field-based research I am proposing would enable me to assess and compare the extent to which Jewish day schools suppress or nurture a sense of play at all ages. My research design will draw from the successful field-based research methodologies I used in research first for my dissertation and then later in research for my book about moral moral education. This proposed study will include shadowing, interviewing school personnel and students, artifact analysis and participant observation. I will use my findings to make a unique call for fellow educators to cultivate and promote playfulness for moral good, affirming our students’ character strengths while reducing anxiety and depression in students in all age groups.