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Modern dating can feel like a never-ending loop of “maybe this will work,” even when the red flags are waving right in front of you. In this episode of FiftyTwo, elite matchmaker and dating coach Anna Morgenstern joins the conversation to break down one of the biggest reasons people stay stuck in dating: ignoring boundaries and hoping the wrong person will change. With over a decade of experience helping high-achieving men and women across the U.S., Europe, and Israel find aligned, lasting relationships, Anna shares what actually works when it comes to dating with intention. From spotting red flags early to being selective about second and third dates, this episode is packed with practical guidance designed to save you time, energy, and emotional burnout. This episode unpacks a real-life dating scenario many listeners will recognize, being drawn to someone attractive and fun who is fundamentally misaligned on kids, commitment, or long-term goals. In this episode, you’ll learn: 1️⃣ Why being selective about second and third dates is key to long-term dating success 2️⃣ Why so many people convince themselves they can change someone’s mind about kids or commitment 3️⃣ How to hold firm boundaries without feeling mean, rigid, or “too picky” 4️⃣ The difference between values and boundaries, and why both matter deeply in dating 5️⃣ How to move on from someone attractive who isn’t aligned with your future 6️⃣ Why you should date soulmates, not bodymates, and how to tell the difference If you’re ready to stop settling, stop hoping, and start dating with clarity and confidence, this episode is for you. 🎧 Press play and date smarter. #FiftyTwo #DatingTips #RelationshipGoals #LifeCoaching #Attraction #LifeCoach #Explore #Commitment #DatingAdvice #Love #Matchmaker #matchmaking #DateWithIntention #Romance #SelfGrowth #DatingCoach #Communication #Dating #Success #SingleLife #GrowthMindset #DateNight #CoupleGoals #KnowYourWorth #TrueLove #ForYou #ForYourPage #Single #relationshiptips #Bossbabe #Date #TrustTheProcess