#80: Dating Over 50 is Actually The Best Time

Wanting love and being ready for it aren’t the same thing. You might be on the apps, going on dates, even hiring a matchmaker—but if you keep finding yourself in the cycle of “hot and heavy” followed by fade and fizzle, the problem may be pacing. In this episode, Hilary unpacks the anxious dating behaviors that push love away and she lays out five concrete ways to date with emotional security rather than a sense of urgency. From keeping your schedule intact, to knowing when to hold back on texting or intimacy, Hilary shows you how to stop spiraling into fantasy and start building real connection—without losing yourself in the process. If you’ve ever skipped Pilates to wait for his call, or decided you were all-in by the third date, this conversation is your reset.    Episode Highlights: Wanting love vs. actually being ready for it — why they’re not the same The role of pacing and how falling too fast sabotages connection Matching his effort, not his potential, to avoid heartbreak   Episode Breakdown: 00:00 Are You Really Ready for Love? 03:27 The Pitfalls of Falling Too Fast 04:52 Five Ways Women Date with Confidence 05:03 Tip 1: Stay Focused on Your Own Life 06:05 Tip 2: Keep Early Dates Short and Intentional 07:08 Tip 3: Match His Effort, Not His Potential 07:51 Tip 4: Delay Physical Intimacy 09:15 Tip 5: Don't Build a Bond Over Text 10:08 Attracting Emotionally Available Men   Healthy, emotionally available men are attracted to confidence, patience, and balance—not eagerness or desperation. Date from security, and you’ll naturally filter out the wrong men while attracting the ones who are truly ready.   ✨ I’m Hilary Silver, LCSW, former psychotherapist turned master coach and founder of Ready for Love. I help high-achieving women show up in love as confidently as they do in their careers. 💡 Through this podcast, I share my WOMAN-centered, SELF-centered approach—time-tested methods that blend psychology, brain science, relationship skills, and no-BS dating advice. 🎙️ Since 2017, we’ve helped over 10,000 women with a 98% success rate, making Ready for Love the #1 program in the world for women who’ve tried everything else.   👉 Watch Hilary’s free masterclass: https://readyforloveinc.com/masterclass Or apply for a free breakthrough call with her team at https://readyforloveinc.com/apply

Most women I talk to over 40, 50, and 60 say the same thing: “I never thought I’d be here, dating at this stage of life.” And let’s be honest, midlife dating often gets a bad rap. But the truth? It can be the BEST time in your life to find real love… if you know how to approach it. In this episode, we talk about why dating now can be easier, more authentic, and more fulfilling than ever—and how shifting your perspective can change everything.   Episode Highlights: Why dating now can feel easier and more authentic than ever The freedom that comes from wanting—not needing—a partner How showing up as your true self changes who you attract Why self-acceptance is magnetic How trusting yourself shapes every choice you make in love   Episode Breakdown: 00:00 Dating Over 50: Why It’s the Best Time for Love   00:53 Meet Hilary  01:47 Midlife Dating Truths   02:07  Reason 1: Maturity & Clarity   03:44 Reason 2: Desire, Not Need   05:08 Reason 3: Authentic Self   07:06 Reason 4: Confidence & Magnetism   08:52 Reason 5: Self-Trust & Boundaries 10:28 Why It’s Never Too Late for Love     Dating now isn’t about chasing chemistry or proving your worth—it’s about finding a true, equal partnership that adds to your already beautiful life.   ✨ I’m Hilary Silver, LCSW, former psychotherapist turned master coach and founder of Ready for Love. I help high-achieving women show up in love as confidently as they do in their careers. 💡 Through this podcast, I share my WOMAN-centered, SELF-centered approach—time-tested methods that blend psychology, brain science, relationship skills, and no-BS dating advice. 🎙️ Since 2017, we’ve helped over 10,000 women with a 98% success rate, making Ready for Love the #1 program in the world for women who’ve tried everything else. 🎯 Watch my free masterclass to learn the proven 4-step Ready for Love Method: https://readyforloveinc.com/masterclass 💬 Apply for a free Love Breakthrough Call with my team: https://readyforloveinc.com/apply

Blind spots can quietly wreck your dating life long before you realize they’re there. And for high-achieving women, they’re sneaky. You can be doing all the “right” things on paper and still keep ending up with the wrong men—or no men at all. Hilary’s breaking down the four biggest ones she sees over and over again. Are you sending mixed signals without realizing it? Mistaking career confidence for genuine self-worth? Letting yourself be chosen instead of actually choosing? Or telling yourself you’re “working on it” when nothing has actually changed? Each blind spot comes with a hard truth and a way forward. And once you see them, you can’t unsee them—which is exactly how you stop getting in your own way.   Episode Highlights: Why mixed signals can repel the kind of partner you actually want The difference between situational confidence and genuine self-worth How “being chosen” keeps you stuck in relationships that don’t fit The myth that dating is a numbers game (and what really works) Why self-awareness is the fastest way to change your love life   Episode Breakdown: 00:00 How Blind Spots Block Love 01:04 Hilary Silver and Ready for Love 01:36 Blind Spot #1: Ambivalence in Dating 04:15 Blind Spot #2: Low Self-Worth in High Achievers 07:04 Blind Spot #3: Waiting to Be Chosen 09:23 Blind Spot #4: Hoping Love Just Happens 12:22 How to Attract the Love You Want   Ready to stop being your own biggest obstacle?  Apply for a call with Hilary’s team to see if Ready for Love is the right fit for you: hillarysilver.com/apply

He disappears. No explanation, no closure, just gone. And you’re left questioning everything: Did I do something wrong? Was any of it even real? In this episode, Hilary calls out the emotional whiplash of ghosting and gives you three power moves to shift out of helplessness and back into your worth. And no,  it’s not about getting answers from him, it’s about giving closure to yourself. If you’ve ever been left on read and spiraled into doubt, this conversation is your emotional reset.   Episode Highlights: Why ghosting feels like betrayal, even if it wasn’t serious The trap of psychoanalyzing him (and how it keeps you stuck) Three power moves to stop the spiral and reclaim your self-worth How to make peace with the ending, without needing his permission   Episode Breakdown: 00:00 The Pain of Being Ghosted 02:53 Why Trying to Understand Him Keeps You Stuck 05:11 Power Move #1: Take Inventory Without Self-Blame 06:17 Power Move #2: Detach Your Worth From His Behavior 09:02 Power Move #3: Redefine the Experience and Reclaim Closure 11:20 How to Heal and What Comes Next   Being ghosted doesn’t mean you’re not worthy. It means he couldn’t meet you where you are. And thank God he’s gone before you invested any more of yourself. 💻 Watch Hilary’s free masterclass:  https://hilarysilver.com/masterclass/ 💖 Apply for a breakthrough call: http://hilarysilver.com/apply

You’ve got your life together: thriving career, financial independence, emotional intelligence, and yet your love life? A hot mess of emotionally unavailable, underemployed, or unstable men. What gives? In this episode, Hilary calls it like it is: this pattern isn’t about the men. It’s about you. More specifically, your subconscious beliefs, unresolved self-worth issues, and fear of real intimacy. Hilary breaks down 7 brutally honest reasons smart, successful women keep dating down—and how to stop. From choosing men who need you so they won’t leave, to settling for “projects” instead of partners, she gets to the root of why high-achieving women sabotage their own love lives.   Episode Highlights: Why you freeze (or flee) when a high-quality man actually shows up How caretaking can be a way of earning love when you don’t believe you’re enough The hidden fears that drive you to choose men who feel “safe” but drain you Why identity work, not another dating strategy, is the real key to change   Episode Breakdown: 00:00 Why Smart Women Keep Dating Down 01:25 What “Dating Down” Really Means 03:10 Reason #1: Feeling Not Good Enough 05:06 Reason #2: Tying Your Worth to Being Needed 07:03 Reason #3: Fear of Abandonment 10:15 Reason #5: Fear of Real Intimacy 14:29 Reason #7: Dating from Loneliness 16:03 How to Break the Pattern for Good   Hilary doesn’t just name the problem, she offers the way out. Because when you stop outsourcing your worth, everything shifts. Want the kind of love that matches the rest of your success? Start by becoming the version of you who actually believes she deserves it. 🔗 Learn more about Hilary’s Ready for Love program: http://hilarysilver.com/apply

Everyone’s suddenly an expert on attachment styles. Anxious, avoidant, disorganized—it’s all over your feed, and maybe even your therapist’s office. But here’s the truth: if you’re trying to use attachment theory to decode every date and relationship, it’s keeping you stuck. In this episode, Hilary is  breaking down why obsessing over your (and his) attachment style is doing more harm than good, and what actually matters when you’re looking for real love. If you’re a smart, self-aware woman who’s done the work but still isn’t seeing results in your love life, this might be why. Because knowing better doesn’t automatically mean doing better. And the answer isn’t more information—it’s radical self-trust, embodied confidence, and knowing how to assess how a relationship feels instead of overthinking why someone acts the way they do.   Episode Highlights: Why therapy, books, and expert advice often lead to “knowing better but not doing better” The trap of over-intellectualizing your love life What to look for in a relationship that actually matters How long-term love evolves, and why labels won’t help you grow it   Episode Breakdown: 00:00 Why Attachment Styles Are Keeping You Single 02:21 Information Doesn’t Equal Transformation 04:46 The Problem with Overthinking and Intellectualizing Love 06:06 The Danger of Labeling Your Partner (or Yourself) 08:02 What a Healthy Relationship Actually Looks Like 09:16 Stop Fixating on Him, Focus on You   If you're ready to stop psychoanalyzing every text and start showing up as the woman who knows what she wants and how to get it—this episode is for you. 🎧 Watch the free masterclass: https://hilarysilver.com/masterclass/ 📞 Apply for a call with our team: https://hilarysilver.com/apply/ 🔗 Ready for More Membership Waitlist → https://hilarysilver.com/waitlist/

You’ve got the career, the confidence, the killer heels… so why are all the men you're meeting either emotionally unavailable, totally underwhelming, or gone after two dates? Here’s the hard truth: It’s not about them. It’s about you. Not because you’re broken or “too much”, but because there’s a disconnect between the woman you look like on the outside and the one you’re being on the inside. And good men? They can feel that.   Episode Highlights: The subconscious beliefs sabotaging your love life (yep, even if you’re “putting yourself out there”) Why men aren’t intimidated by your success, they’re turned off by your walls The hidden ways your self-talk is killing your vibe And what it really takes to attract a healthy, high-caliber man   Episode Breakdown: 00:00 Why You’re Not Meeting Good Men 03:04 The Myth of the Secret Place Men Are Hiding 04:17 Reason #1: Limiting Beliefs Are Repelling Love 05:31 Reason #2: Fear of Intimacy and Vulnerability 08:01 Reason #3: Looking High-Value on the Outside, Not Inside 10:08 You Must Become the Woman Who Can Receive Love 11:44 Real-Life Stories: When Good Men Start Appearing 12:26 Stop Searching. Start Showing Up Differently   There’s no underground speakeasy of good men you haven’t been invited to. They’re all around, you just can’t see them until you become the woman who’s ready to meet them. Door #3 is waiting. But first, you’ve got to stop playing defense and start playing real. 💥 Apply for a breakthrough call: https://hilarysilver.com/apply

Ever feel like you're on date #200, with the same guy? In this episode, Hilary breaks down emotional unavailability for what it actually is: a lack of real intimacy. If you're attracting men who can't go deep, there's a reason. And it may have more to do with you than you think. For high-functioning women especially, this is a sneaky blind spot. You might be warm, flirty, and fun—but still totally guarded. You might talk about your emotions, but not feel them in real time. And that performative intimacy? It’s what keeps real connection out of reach.   Episode Highlights: Why emotional unavailability isn’t just a “man” problem The two biggest reasons people avoid true intimacy The subtle difference between being expressive and actually being emotionally available How to finally break the pattern by turning inward   Episode Breakdown: 00:00 Why “200 First Dates” Is a Red Flag 01:51 What Emotional Availability Actually Means 02:45 Fear of Vulnerability and Rejection 04:19 Emotional Expression Is a Learnable Skill 06:06 Why Surface-Level Connection Isn’t Enough 08:04 How to Break the Pattern for Good   If you’re done settling for surface-level connections—or being the one who always “catches feelings” first—this is the episode for you. 💥 Ready to stop the cycle for good? Watch Hilary’s free masterclass for high-achieving women who want real, lasting love → http://hilarysilver.com/masterclass 🔗 Ready for More Membership Waitlist → https://hilarysilver.com/waitlist/

You saw the red flags. You felt the gut punch. And still, you stayed. If you’ve ever looked back on a relationship and thought, “How did I miss that?”, this episode is for you. Hilary breaks down why smart, high-achieving women override their instincts—not because they’re clueless, but because they want love so badly they talk themselves out of what they already know. The chemistry was strong. The checklist looked good. And he did have potential. So you minimized, rationalized, and convinced yourself it wasn’t that bad… until it was.   Episode Highlights: What happens when logic wins out over emotion (and why that’s not always a good thing) The quiet ways high-functioning women betray themselves in love How “I see the good in people” becomes a self-sabotaging mantra Why your discomfort is more trustworthy than you think The link between intuition and emotional fluency How to stop brushing off the ick and start paying attention to it   Episode Breakdown: 00:00 Recognizing Relationship Red Flags 02:29 Reason 1: Desire for the Ideal Relationship 04:15 Reason 2: Disconnection from Emotions 06:05 Reason 3: Seeing Only the Good in People 08:09 Understanding and Trusting Yourself 09:23 Finding the Sweet Spot in Relationships   Whether you're single and hopeful or already in a relationship, this conversation will challenge how you listen to your instincts, manage discomfort, and define what “being a good person” actually means. Ready to stop turning the wrong man into the right one? Start by learning how to trust yourself again. Watch Hilary’s free masterclass for high-achieving women who are done ignoring red flags and ready to choose differently.  👇 Get it Now! 🔗 Free Masterclass for Single Women → http://hilarysilver.com/masterclass 🔗 Ready for More Membership Waitlist → https://hilarysilver.com/waitlist/  

If you’ve been told to "just be more feminine" to attract a high-quality man—this episode is your permission slip to roll your eyes and delete that advice forever. In this episode, Hilary unpacks the real meaning of feminine energy for strong, high-functioning women who are tired of being told to play small. She’s calling BS on the idea that you need to be more “demure,” wear more pink, or act helpless so a man can feel useful. (Spoiler: You don’t.)   Episode Highlights: Why the “let him take the lead” narrative is secretly sabotaging your love life What feminine energy actually looks like when you’re powerful, grounded, and self-sourced The childhood beliefs that locked you into over-functioning and under-receiving One 30-second shift to move from drive into flow (no crystals required) Episode Breakdown: 00:00 Feminine Energy Myths 01:37 Misconception #1:You need to Let Men Help You 02:15 Misconception #2:You Need to be Demure 03:31 The Deeper Truth About Feminine Energy 05:20 Becoming Magnetic in Love 06:36 Queens Don’t Chase   Ready to stop playing damsel and start sitting on your damn throne?  👇 GET STARTED: 🔗 Free Masterclass for Single Women → http://www.hilarysilver.com/masterclass 🔗 Ready for More Membership Waitlist → https://hilarysilver.com/waitlist/ 🎥 Watch Next: The Over 40 Glow Up → https://youtu.be/9tcA0E1uFAE