The Hilary Silver Podcast - 4 Dangerous Dating Blind Spots Revealed

Episode Date: August 29, 2025

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

I've personally worked with tens of thousands of women over the last 25 years, and I can tell you there's nothing more frustrating, confusing, or even dangerous than not being able to see yourself or a situation clearly. Blind spots are the things that you're doing or the ways that you're thinking that are actually working against you, but you can't see it. In fact, you might think that you're doing something good or helpful when really it's backfiring and keeping you stuck. And when you don't realize something's a problem and you just keep doing it over and over again, you're going to get the same outcome. Just digging yourself in deeper and deeper without even knowing it. So today I am sharing the four biggest blind spots that I see in high

achieving women who are dating and looking for love. And by the end, I promise you'll walk away with at least one powerful realization about why love has been elusive and how to finally get out of your your own way. 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, let's just get straight to it. The first blind spot that most high achievers have about love and relationships is ambivalence, which is when you want something and you kind of don't want it at the same time. So many of our Ready for Love clients say they want a partner to do life with, and they are out there dating and doing all the things.

But under the surface, there's another voice, one that says, what if I choose wrong again? What if I mess it up? What if I lose myself in the relationship again? What if I get hurt? I don't want to give up my freedom, my independence. in my autonomy. And so without realizing it, they're out there dating, but they're doing it with all this fear and doubt and anxiety and second guessing and questioning themselves, wanting it, but also not wanting it at the same time. That is classic ambivalence. And it's what I call

driving with one foot on the gas and one foot on the brake and wondering why you're not getting anywhere. And here's the thing most people don't know. You simply can't fake it, Going through all the motions on the surface, but having these deep down conversations with yourself actually blocks what it is that you want from coming into your life. It's a vibe and it's an energetic signal and it creates confusion in your field, which I know sounds woo, but it's true. And it sends mixed messages to every man that you meet. And it sends mixed messages out into the universe itself. I want this thing, but also maybe I don't. I'm ready for it, but I'm ready for it, but I'm I'm scared, so maybe never mind.

You say that you're open, but you're also guarded. You say you're ready, but you're terrified. If you're not ready for it, it will not come, period. This energy will block any good thing that you want from coming into your life. So it will just never happen. So while you're out there, trying your best and spending your time and your energy and all this effort and maybe even money on apps or matchmakers, instead of attracting what you want, want, you keep attracting more of what you fear and create more evidence that it can't happen for

you, which is attracting emotionally unavailable men or men who won't commit or men who aren't at your level or men who ghost or who seem great at first but then disappear. Can you see how this blind spot of ambivalence keeps you from getting what you want and it makes you your own biggest obstacle? And it's why we are having this conversation today so that you can just get out of your own way. And in order to get out of your own way, you must do the work on all the reasons that you keep putting your foot on the brakes and resisting and why you're afraid and all the what-ifs so that you can just be free and clear to let love in. Okay. So the second blind spot is dating from a place of lack, lack of worth, lack of confidence, and lack of self-trust. And instead,

you're dating with this insecurity and self-doubt and fear and scarcity. And this is one of the most deceptive blind spots for high-achieving women because you think of yourself as a smart, powerful, and confident woman. Because you are that at work, you point to all of your success and your accolades and your achievements and your accomplishments and maybe even the money in the bank, the letters behind your name, and you say, yes, see, I'm confident, look at all that I've done. So you've climbed the ladder and you have achieved this level of success that most women and anyone would envy.

And there is so much to be proud of. Yet, your track record with men does not reflect that of a woman at your level. In fact, the truth of your relationship experiences reveal anything but a woman who truly genuinely knows her worth and her value, doesn't it? So you have situational confidence, not true confidence. And so here's the thing you really have to hear today. Your worth has nothing to do with your accomplishments or anything that you've built for yourself externally in your life, your looks or anything else like that. Your true worth is inside of you. And it's been neglected all this time

while you've been busy chasing and proving your worth and enoughness in your external accomplishments. But if we take away all of these trophies on your man, mantle, what is left? Nothing but a little girl inside of you who so desperately wants to be seen and loved and known. This is the secret plight of the high achiever. It's a fact, a little known fact, but a fact nonetheless, that high achieving women often secretly struggle with low self-worth and low self-esteem. Because the truth is, if you really knew your worth and your value, you would not tolerate the things that you have. You wouldn't overfunction, people please, or feel anxiety around whether he likes you and picks you, and you wouldn't

care so much what other people think about you all the time. You also wouldn't stay too long with the wrong men and try to make it work. You wouldn't settle for anything less than you deserve or desire in a partner or in a relationship. You wouldn't stay too long with the wrong men and try to make it work. And you wouldn't be confused about whether he's good for you. You would just know. So until you address the deep lack inside of yourself, your not enoughness, quality love and relationships will always remain out of reach. The third blind spot I see is high achieving women waiting to be picked instead of doing the picking or waiting to be chosen instead of doing the choosing. This one is incredibly common, but almost no one talks about

it. So you meet someone who seems nice, and because he shows interest, you think, maybe this could be something. Maybe he checks some of your boxes, or maybe there's chemistry, or maybe he's just a man who pursues you when so many others have flaked. You are interested only because of his interest in you. So whatever the reason, you let his attention dictate your attraction, you let his pursuit determine the path forward, and you get flattered, way too easily. I might add. So you go with the flow and see where it goes. Maybe even knowing the whole time that he's not your guy, but going along anyway, because nothing else is coming along. Maybe you think this is as good as it gets. Better hang on in case what I really want just doesn't happen. But here's

the problem. You're not choosing. You're just responding. And when you're in your worth, you don't wait to be picked. You get clear about who you are and what you really want and you select accordingly. This isn't about chasing men or being the pursuer. It's about showing up with discernment. Having a clear sense of what you need and want in a partner and not wasting time entertaining anyone who doesn't align with that. Because when you just go along, you take what you're getting rather than getting what you want. It's important to know why you picked wrong in the past and how to change your attraction pattern if that's what's needed. And you also need to understand what makes a good partner for you. Understanding your ideal man criteria, which is what I call it,

is more than a list on paper. It's actually trusting yourself to know it when you see it in person when he's actually standing there right in front of you. Otherwise, you end up settling, bargaining, compromising, or negotiating with yourself, or just continuing to go along with anyone who pursues you. Again, being interested in him only because of his interest in you. This is not the way to a truly great relationship at all. And finally, this is the blind spot that wastes the most time because it tricks you into thinking you're doing something when you're really just spinning your wheels and calling it progress.

It's thinking love will just magically happen, thinking that you're working on your love life because you're thinking about it and trying and dating. But you're actually not really making any real progress or taking any real action. It's hoping, praying, wishing, dreaming, waiting for the right guy to just come along. It's talking about it with your girlfriends. It's thinking that putting yourself out there to find love is enough to actually find love.

It's dating a lot and going on more dates and thinking it's a numbers game. I've literally heard people say it's just a numbers game. It's continuing to get out there and focusing on which app you're on and your profile and your pictures. and the men and the events and the coffee dates. It's walking into any room and scanning to see if maybe your guy could possibly be here. It's believing that you just need to find the right guy and you'll be good to go. Or alternatively, it's taking time off from dating when you just need to take a break and you need a breather. But while you're taking a break, you're not doing anything to work on yourself while you're taking

this time out and sitting on the bench. In this case, you're sitting there and time just passes. you buy. And then when you decide that you are ready to try again, you get out there and nothing has changed because you haven't done anything to work on yourself. So women will get out there and immediately experience the same exact issues as before. So here's the truth. Thinking about dating in relationships is not working on it. Learning about feminine energy or memorizing what some influencer says to text him to get another date is not working on it. And actually going to therapy is not working on it. And just getting out there and dating and dating and dating is not

working on it. Meanwhile, you're going about it all wrong and it only reinforces the belief that maybe love isn't for you or that all the good ones are taken or that you just have to settle for a life without love. Listen to me right now. Do not give up until you have actually worked on it. Dating while you are completely unaware of yourself is a setup for exhaustion. and disappointment. Nothing changes unless you change. Remember our old friend Einstein said, doing the same thing over and over again, but expecting different results is insanity. That's that famous quote by him. I just call it denial. Refusing to look at what is going on and avoiding the real issues or just trying so hard to figure it out, but looking in all the wrong

places is denial. If your outer results keep repeating, it's not what's happening. It's not what's out there. It's about something in here. It's something you're not seeing. And that is the best news I can give you. If you are somehow the problem and you are willing to look in the mirror, then you are very, very quickly the solution. We are all always our own biggest obstacles. We are all always our own problem. And personally, I want to be the problem. Because if I'm the problem, then I can get to be the solution. I can do the work. I can shift, evolve, learn, grow, learn a skill, change my mindset, whatever it is that I need to do. But if I commit to it, I can change it and then I always end up getting what I want. So I hope having this conversation today and revealing these

four blind spots helped you see what needs to change for you to start having better results in your love life. If you're ready to take the next step and to see if and how we are a fit to help you. Specifically, apply for a call with my team. Just go to Hilarysilver.com forward slash apply. Thanks for being here and please share this with anyone who needs to hear this and I'll see you next time.