Finding love in 2025 is complicated. Dating apps have rewritten the rules, traditions don’t always fit, and so many people are left wondering: am I doing this right?In this episode of The HelloPrenup Podcast, Julia sits down with NYC-based matchmaker Anna Morgenstern and her husband Zachary Speiss for a heartfelt conversation about love, culture, marriage, and the very real challenges of dating in today’s world.Anna has spent years helping others navigate the ups and downs of finding love in New York City, but here she shares her own story. From swiping on dating apps to meeting her husband, to blending their immigrant backgrounds and perspectives on marriage, Anna gets candid about what it takes to turn a match into a true partnership.And in one of the most powerful parts of their story, Anna and her husband open up about their decision to create a prenup—and how that process actually strengthened their relationship. They explain how sitting down to draft an agreement forced them to have vulnerable, necessary conversations about money, values, and long-term expectations—conversations they may never have had otherwise. What could have felt intimidating instead became an exercise in trust, transparency, and building a foundation for their future together.Throughout the episode, Anna also shares the biggest mistakes she sees singles making in today’s dating scene, the red flags and patterns that keep people stuck, and the subtle mindset shifts that can transform the way you approach love. Her husband offers the other side of the story, showing what it really looks like to grow together in a marriage that honors both individuality and partnership.This episode is part love story, part expert advice, and part cultural narrative. It’s about what it means to build a marriage in a modern world—and why the toughest conversations often bring you closer.It doesn't matter if you’re single and swiping, preparing for marriage, or already deep into your partnership...this is a reminder that love doesn’t follow a script. It’s written through the choices you make, the honesty you share, and the courage to ask the hard questions together.Follow Anna at @annamorgenstern on Instagram and her website annamorgenstern.comWhether you're single, engaged, married, or divorced, the HelloPrenup Podcast is committed to presenting you the best-in-class thought leaders in the love, wedding, marriage, and life planning space. Connect with HelloPrenup: Website Instagram TikTok YouTube

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