The Hilary Silver Podcast - #80: Dating Over 50 is Actually The Best Time

Episode Date: September 5, 2025

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.   🎯 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

Most women I talk to say something like, I never thought I'd be here, over 40 in dating, over 50 and dating, over 60 and dating. This is not where I thought my life would be. And let's be honest, when women talk about dating at midlife, it's usually with dread. You imagine balding men with ED, carrying pot bellies, bad habits, and baggage. It can feel like the dating pool is more like a puddle, slim pickings and diminishing returns. You know exactly what I'm talking about. But here's the truth. There are plenty of successful, healthy men who want the same things that you do. And dating as a high-achieving woman over 50 is actually the very best time

in your life to be dating if you know how to approach it. And that's what we are going to get into today. Hi, it's Hillary. Welcome to the Hillary Silver podcast. Thanks for tuning into the conversation today, if you haven't already, it would mean so much to me. If you'd take a minute to just click that five-star rating on your podcast app, leave a review and subscribe so you never miss one of my episodes. And if you're enjoying this podcast, please consider sharing it with a friend because if you like it, they will probably like it too. Okay, so let's talk about dating over 50. Really, it's more like dating midlife. And why it's just not still possible, but why it is actually the best time in your life to find real love.

Reason number one, you're not just older. Time has aged you in the best of ways. You have the benefit now of showing up in your love life with maturity. You're not naive, impulsive, and self-doubting. Instead, you've learned to trust yourself and be patient. You don't rush into things but take your time because you know it takes time to really fully know someone. You have clarity.

You know exactly who you are, all of your strengths and your flaws and your faults and your insecurities and your triggers and patterns. It's like standing in a 360-degree mirrored room. You see it all and you really know yourself. This self-awareness is the only way to understand the kind of partner that's best for you. You know what you really need and want and trust yourself to never settle ever again. So now you're not chasing chemistry, but instead looking for character. and you don't fall for charm, you expect compatibility and in more than just the surface level ways. And you're healed, healthy, and whole. Having resolved some of your core wounds and you've

accepted responsibility for your patterns and choices along the way, so you're not attracting or drawn to those who haven't done their work. And you're attracting men who are also healthy and whole. Because remember, like attracts like. So bottom line here, you're a grown-up. You're not just older, you're mature, you're seasoned, and you're wise. And that kind of wisdom and clarity is vital. So rather than seeing this as old people dating, see it as dating as the very best version of yourself, something the younger version of you had yet to become. And when two grown, whole people come together, it's magic. Reason number two, you don't need a man. You want a true equal partner to share your life with. So you're approaching your love life from a

place of desire. And it's an entirely different vibe. So let's be honest, in your 20s or 30s, you probably needed a partner for safety, for stability, for children, for financial support and interdependence, for validation of your deservability and enoughness. Not that that's what we want, but that's definitely where most of us were at that time in our lives. And also to fulfill the master plan of creating the life everyone expected you to live. I can't tell you how many times I've heard both men and women say, I got married because it was the next expected thing to do. But now, you've built your own life, you're independent, you've raised the kids, you've made your money, you've proven to yourself and anyone else that you are enough and you can do it all.

which means that now, if you choose to share your life with someone, it's not out of necessity, desperation, or societal or family expectation. It's simply and only from desire. And that shift is everything. When you let go of that outcome, you are that much more likely to actually get it because the energy behind everything that you do is bursting with self-worth, strength, and dignity. You know if it's not enough, it's a no. If it's not good enough, it's a no. You want love, but only the kind that adds value to your already beautiful life. And that's what makes you truly magnetic. Reason number three, you're done pretending and instead are just your true, authentic self. So in your younger years, dating was more of a performance and love was to be earned. You had to win him over and get him to see how amazing you are. you tried to be what he wanted. Maybe you downplayed your success or softened your opinions or held back your truth to keep the peace or just bent over backwards to get him to see you as the one and pick you and like you. You accommodated. You were agreeable. You were anything that you thought that you

needed to be to get him and keep him, which is all part of our conditioning as girls, by the way. But now that you know better, that does not work for you. Being that way doesn't lead to authentic real connection or satisfaction in a relationship, and it doesn't lead to real love and intimacy. So you're done abandoning yourself and shape-shifting. You're not looking to get picked anymore. You're doing the picking. And when you date just being your true, raw, unfiltered, unapologetic, authentic self,

you don't get into just any relationship. You get into the right one. and it's the kind of love you can only experience when you are fully expressed and seen for exactly who you are. So if you're listening to this and you're thinking, that's what I want, I want to feel like that when I'm dating, then watch my free masterclass. You'll learn the proven four-step Ready for Love method that I've been using with our clients since 2017 with women just like you. So go to readyforlove inc.com forward slash masterclass to watch it. So reason number four, You are at your very most radiant and sexy. At this age, yes, it's true. You've made peace with your

past. You have forgiven yourself all of your flaws and your faults. You've accepted your body. You love who you are. And even though we may have more wrinkles and our bodies aren't what they were, the complete acceptance of ourselves and being comfortable in our own skin, that is true confidence and it is sexy as hell. My favorite thing about getting older is, is not giving a fuck anymore about what anyone else thinks. And when you don't care what anyone else thinks, you are irresistible. You're not seeking acceptance or approval because you've given that to yourself. You're impervious to criticism or judgment because at the end of the day, the only opinion that matters about you is your own. And you look good because you wear what

you want to wear. And you look amazing because you want to look amazing. You wear what you want, for you not to get male attention or approval, and definitely not to be validated by some guy who may or may not text you later. And this is very important right now, when a woman no longer needs flattery to feel good about herself. And when she is whole and full, rather than starving for love, validation, or attention, she becomes immune to love bombing, immune to rejection, manipulation, or any other BS. That energy is your superpower. It becomes like a force-fueled around you, and that kind of energy is rare, radiant, alluring, and intoxicating.

And finally, reason number five, you trust yourself, and that changes everything. You are no longer wondering if you're good enough or worthy or deserving or lovable. You know you are, and you understand it has nothing to do with your achievements or your accomplishments either. You were born worthy, and nothing has changed no matter what you have been through in your life. So you are not hiding, you are not afraid of rejection or abandonment, and you are no longer trying to get someone to like you. And this changes everything about how you navigate your life, not just your love life and

dating, but how you operate in all areas of your life. You trust yourself to always do what is best for you no matter what. You'll never betray yourself or abandon yourself ever again, not for him and not for anyone. You've learned that you are the most important person in your life. life. Your needs, wants, opinions, and boundaries are to be respected and honored by you first and foremost. And you understand that you come first. After all these years of taking care of everyone and everything else and putting yourself last and taking crumbs and scraps has been your own doing. And you are done with that. This is high value energy. Your relationship with you and how you treat yourself is

everything, knowing that you come first and that you go first means that you trust your gut and listen to yourself. You don't settle, override your intuition, or silence yourself to keep the peace. And you don't fall for manipulation or gaslighting, but instead you listen to yourself and you know you will never, ever settle ever again. When you have self-trust like this, this foundational component of a relationship with you, you show up fearlessly. and open and ready to just let love in. So if you've been telling yourself the story that it's too late or too hard or not worth of trouble, I hope this episode gave you a lot to think about and energized you because the truth is dating in your midlife over 50-ish can be better than ever.

Thanks for being here and make sure to subscribe, share your thoughts with me, and share this episode with somebody who needs to hear it. And remember to watch the free masterclass at readyforloveink.com masterclass. And if you've already done that, by the way, you can apply for a free love breakthrough call with my team at readyforloveink.com forward slash apply. See you next time.