In this episode, we explore the deeply personal journey of dating after loss with relationship expert Whitney Kobrin, who shares her own transformative story of finding love again after her husband's unexpected passing. Whitney opens up about navigating the complexities of honoring her late husband's memory while embracing new love, offering raw insights into the delicate balance between grief and growth. From the practical challenges of estate planning to the emotional hurdles of reentering the dating world, this conversation provides invaluable guidance for those facing similar crossroads. The episode delves into the often-unspoken aspects of dating after loss, including when to have difficult conversations with a new partner, how to handle others' judgments, and the importance of building resilience before stepping back into the dating pool. Whitney shares how her personal experience shaped her career transition from corporate HR to becoming a dating coach and matchmaker, bringing a unique perspective to helping others find love after loss. Through intimate stories and professional insights, this episode offers a beacon of hope for those wondering if and when they're ready to open their hearts again, while providing practical tools for navigating modern dating landscapes with authenticity and self-trust.