In this interview, the Rosh Yeshiva, Rabbi Yonatan Dorfman, interviews Doctor Yaakov Freedman about matters surround grief and depression, common rabbinical problems, and the line between obsession and frumkeit. Dr. Jacob L. Freedman is a board-certified psychiatrist practicing in both Massachusetts and Israel, with a private practice in Jerusalem. He completed his medical training at the University of Massachusetts Medical School and Harvard’s Longwood Psychiatry Residency, where he was Chief Resident. Dr. Freedman has worked in diverse settings, including emergency psychiatry, inpatient care, and outpatient psychotherapy, and has been involved in medical education and leadership roles, such as Assistant Professor at Tufts University and medical director at Bayit Cham in Israel. Additionally, he is a healthcare consultant, public speaker, and researcher, with interests in medicine, ethics, and Jewish thought, as well as having worked with many notable rabbanim throughout his career. Chapters: 0:00 - Intro 1:35 Guilt & Depression 9:35 How Can We Fix It? 21:31 Mistakes that Rabbanim make 24:42 What About Pulpit Rabbanim? 27:56 The Pulpit Rabbi Toolkit 29:46 Problems With Parents and Dating 36:53 Obsessive vs Genuine Connection 47:20 ADHD All rights reserved by Yeshivas Yedid HaMelech Yedidhamelech.org [email protected]