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In this episode, Rabbi Greenwald and Rabbi Yudkowsky tackle a question every parent faces: how do we raise children who know how to be good friends? They discuss how to model and empower children to share and get along with each other, and examine the role of character in interpersonal relationships and obligations. The conversation also addresses boundaries—what to do when a child feels used, overlooked, or bullied. It offers practical guidance for dealing with children's feelings, communicating with other parents or the schools, and creating a safe environment. It also discusses how to help a child deal with conflicts and stand up for himself. A thoughtful, practical discussion about raising children who can give generously—without losing themselves. ----------------------- Check out Rabbi Greenwald new book: https://www.artscroll.com/Books/9781422645352.html

In this conversation, Rabbi Yudkowsky and Rabbi Greenwald delve into the subject of friendship, for ourselves and for our children. Rabbi Greenwald outlines three fundamental elements of friendship - the role they play in our lives and the core of true friendships. It also addresses the pain of rejected friendships, especially in children, and how parents can guide their children in building meaningful relationships. Next the conversation touches on the different types of friendships, their benefits, and what sets enduring friendships apart from more transient relationships. It concludes with noting how nurturing and investing in friendships enhances individual and collective well-being. ----------------------- Check out Rabbi Greenwald new book: https://www.artscroll.com/Books/9781422645352.html

Rabbi Yudkowsky and Rabbi Greenwald explore one of the most complex and emotionally charged challenges of parenting: trust. This is episode two of a three-part series focused on what it truly means to trust our children. The rabbis unpack some common fears that if unacknowledged or ignored can block our ability to trust. They distinguish between external compliance vs internal motivation -- obedience driven by pressure or fear and growth that emerges from choice, ownership, and self-direction. They challenge the assumption that constant intervention leads to better outcomes, examining the subversive impact of control on a child’s confidence, agency, and long-term development. The conversation extends into the religious and spiritual realm, considering the difference between cultivating authentic connection to mitzvot and values as opposed to outward conformity. They describe how trusting our children is an outgrowth of trusting ourselves and having the courage to give our children space to struggle, learn, and grow. Ultimately, this episode reframes trust as an act of faith in the process of growth and in our children’s potential. And it explains how meaningful connection—both in parenting and in Avodas Hashem—cannot be forced, only nurtured. ----------------------- Check out Rabbi Greenwald new book: https://www.artscroll.com/Books/9781422645352.html

Building Trust in the Home: Practical Insights for Parenting What does it really mean to build trust with our children, and what quietly erodes it over time? In this episode, Rabbi Yudkowsky and Rabbi Greenwald explore trust not as a technique, but as a way of being in the home. They touch on the subtle messages parents send through consistency, communication, and everyday interactions, and how those messages shape a child’s inner world. The conversation raises difficult and honest questions about control, guidance, and what happens when children struggle or push back. Along the way, the rabbis challenge common assumptions about parenting and invite listeners to reconsider what truly helps children grow into confident, grounded adults. This episode offers perspective, reflection, and a deeper way of thinking about trust, without easy answers or quick fixes. Timestamps 0:00 Introduction and Welcome 0:05 Creating a Trustworthy Environment 1:04 The Marshmallow Experiment 2:12 Nature vs. Nurture in Trust Development 3:31 Teaching Delayed Gratification 4:34 Parental Influence on Trust 5:42 The Role of Consistency and Honesty 8:49 Challenges in Parenting and Trust 15:43 The Importance of Struggles and Challenges 21:12 Guiding Children Through Mistakes 24:27 The Power of Gentle Guidance 25:47 A Fathers Persistent Influence 27:18 Creating a Trusting Environment 28:15 The Impact of Corporal Punishment 31:38 Understanding and Addressing Rebellion 34:35 Building Trust with Teenagers 43:45 Summary and Key Takeaways on Trust and Parenting