#80: Dating Over 50 is Actually The Best Time

11m
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

Listen and follow along

Transcript

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 pick-ins, 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 Ready for Love podcast.

Thanks for tuning into the conversation today.

If you haven't already, it would mean so much to me if 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.

Before we get into the conversation today, I want to talk about what you might have just noticed.

Yes, the Ready for Love podcast.

So here's the deal.

I started the Hillary Silver podcast because I really just truly genuinely wanted to share my transformational philosophy and my methods and my approach that's in the Ready for Love program with all women, not just single women who are looking for love.

But after 80 episodes and 18 months of doing both things, it honestly just got to be too much for me.

When in reality, they are not two separate things.

Getting everything that you want in your love life or any other part of your life always starts with you.

And after getting a lot of great feedback on our Summer of Love series, it just feels like the right thing to do.

So whether you're single and looking for love or you're coupled and in a relationship and are looking for more, the underlying messages in all of my episodes will always be about your relationship with you.

This is a space for bold insights, paradigm shifts, and the straight-up truth about what it really takes to attract and keep love, feel fulfilled, and live your very own best life.

Okay, so let's talk about dating over 50.

Really, it's more like 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 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.

And 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 shapeshifting.

You're not looking to 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 readyforloveinc.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 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 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 field 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.

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 the 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, 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 readyforloveinc.com forward slash masterclass.

And if you've already done that, by the way, you can apply for a free love breakthrough call with my team at readyforloveinc.com forward slash apply.

I'll see you next time.