The Hilary Silver Podcast - Why Can’t I Find Men At My Level?

Episode Date: August 15, 2025

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

If you're a smart, successful, high-achieving women, but you keep attracting, dating, or ending up with men who are just not at your level, this conversation is for you. I see this all the time. Women who have their lives together, crushing it in their careers, making great money, and yet they're dating men who are unemployed, financially unstable, emotionally unavailable, or just who have issues. It's not because there aren't amazing men out there. It's because something deeper is going on.

something inside of you that's keeping you stuck in these patterns. So today I'm going to give you seven brutally honest reasons why successful women date down and more importantly, how to stop. Hi, it's Hillary. Welcome to the Hillary Silver podcast. Thanks for tuning into the conversation. If you're new here, I'm Hillary Silver, former clinical therapist turned master coach. I've been counseling and coaching high performers for 25 years. I'm also the founder of Ready for Love, a company completely dedicated to helping high achieving single women get the love and the life they want by focusing on the relationship that matters most, the one they have with themselves. We are in the midst of an eight-week series I'm calling The Summer of Love. Whether you're single or coupled,

I assure you that there will be something for everyone in these episodes because getting anything you want always starts with you. Dating down is a term that I created. And you use, you with my clients who have amazing careers, they've lived in accomplished life, and are stable, ambitious, and financially independent. Yet, the men that they attract and often end up with don't share that same level of success. They find themselves dating men who are struggling, who are financially or emotionally unstable, underemployed, or unemployed, don't have the savings and retirement that you do. All the way to men who have problems that you are really good at fixing, like addiction issues or problems with their ex, that kind of stuff. Men who are

projects instead of partners. And ladies, projects are for landscaping your backyard. Projects are for work. They are not for your love life. Okay? So ultimately, this means there is an imbalance to the mental, emotional, and financial contribution to the relationship. And you, the woman, end up doing everything, paying for things, being what I call the same. stabilizer for someone who needs stability. And it's exhausting and depleting. So let's dive into the seven real reasons behind this pattern, which, believe it or not, are rooted in your own subconscious beliefs and unresolved issues. Let's face it, if you keep attracting and choosing partners who bring you down, you are the common denominator here, right? If there's a

pattern, then you are the common denominator. There is something inside of you drawing you to that dynamic. And until you are willing to have a look at what's going on, your pattern will only continue to repeat. So let's get into it. Reason number one, deep down, you don't feel good enough for the good guys. In your rational mind, intellectually, you know you're amazing and deserving and you're a great catch. But deep in your subconscious, where things don't always make sense, there's that little voice whispering, that kind of man won't like you. Or you see him out and your initial reaction is, what kind of woman would I have to be to get that kind of man? So when a high-quality, confident, successful man shows up, the kind of man that you say you want

to be with, you shrink. You second-guess yourself. You get awkward. You self-sabotage. You put him on a pedestal and see yourself as less than. Whether you realize it or not, that energy pushes him away. I know that if I saw you walking down the pier at a boat marina, I'd I'd think, ooh, that woman's getting into the yacht at the end of the dock just because of how you look and how you move and how you carry yourself. But when you get to the end of the dock, you look at the yacht and instead turn and get into the little dingy, the little fishing boat next door. Internally, there is a part of you that doesn't feel worthy or deserving to be in the yacht. You internally feel less than or inferior because deep down, part of you feels like you just don't deserve the yacht. even though you look like you belong on it, you don't feel it inside. One woman once told me,

I'll get on the yacht, but then once I'm on, I go hang out with all the wait staff. That's the kind of self-concept we're talking about. So if you don't feel like you deserve to be with that caliber of man, even if you are his equal, you won't allow it to happen. You will sabotage it. He will walk up to you and you clam up or you get awkward or you get insecure or you get nervous, or you push him away, or you say things that aren't true for you. You turn into somebody that you're not. You're just not yourself. You're trying to be somebody better than you are because you think that's who you need to be or that who you are isn't enough. Internally, you shy away from those men because of how it triggers you and makes you feel not enough.

And so you go for the men who aren't at your level. They're not intimidating. I know it sounds crazy, And none of this is conscious, but it is real. I hear it every single day from smart women who are neurosurgeons and lawyers and executives who say they look 10 years younger than they are and they have all the great friends in a fabulous life. It's not at all what we would think is actually happening inside of her head within themselves, but it is. So reason number two, you don't value yourself enough.

If you don't inherently feel valuable just for who you are, then you'll try to create value by turning yourself into a commodity, by being someone he needs. Women have told me what value do I bring if I'm not doing something for him? Dating below your level gives you a role or a purpose, someone to help, fix, rescue, support, or save. Because deep down, you don't feel like just being yourself is enough. So instead, you make yourself indispensable. You earn your place in the relationship by what you do for him.

Women turn themselves into a therapist, a case manager, the business coach, the ATM, or the nurse. One of my clients gave her boyfriend at the time $80,000 to help him catch up on his child support. And when she no longer wanted to be with him, she felt like she had to stay with him until he paid her back. I could not make this up if I tried. Here's the thing. At first, it might feel fulfilling. You feel important. You feel needed. But over time, you don't feel loved for who you are. You feel used, taken for granted, unappreciated, taken advantage of. And that's because the entire relationship is built on what you can provide, what you can do for him, rather than just for who you are. It's transactional. And deep down, you've internalized the belief that love has to be earned through, service, sacrifice, and caretaking. It's a vicious trap. But the important thing here is to see that you're doing this to yourself. And remember that this is what we want. We want you to be the problem. We want your unhealthy patterns, whatever they are, to be of your own doing. Because then you can

commit to figuring it out and get a different result, right? Reason number three, you pick men who need you so they won't leave. This is a big one. And while it might sort of seem similar to the last, it's actually different. If you have a fear of abandonment, you may subconsciously pick men who rely on you, financially, emotionally, logistically, because you believe that if he needs you, he won't leave you. You're somehow protecting yourself against being abandoned. This is when I hear women end up taking care of his kids or having him live with her because he's in between jobs or hasn't settled into something stable for himself since a divorce. Maybe not having him even pitch in towards the mortgage. It's

tough to hear. But if there's any part of you that's afraid of being rejected because you're not good enough, then dating a man who depends on you feels like a guarantee that he'll stay. But here's the heartbreaking truth. These men still leave. And even when they don't, they drain you. They take advantage of your generosity, and they make you feel less loved, less lovable, not more. Because when someone stays out of need, rather than by choice, out of a place of love, it never truly feels safe or secure anyway. This too is a transactional relationship, and it's a setup for both of you to constantly be disappointed. He feels he's never good enough and can't measure up and constantly disappoints you. And he feels emasculated.

and you feel he just can't give you what you want and may even treat you poorly because of how he feels about himself. Either way, you're left empty-handed. Reason number four, you're afraid of being found out. Okay, this is a really sneaky subconscious one here. If way deep down, you feel like you're not good enough, then when you are with somebody who you think is less than you, it will never be discovered that you're the one who's not enough. It's not a conscious decision. It is completely, Unconscious. It feels safe because he can't reject you for not being good enough. Make sense? So subconsciously, you're dating at your own internal level. If you think that he'll somehow discover that you're not worthy or you're not good enough or that you're broken, you won't date somebody who has the power to hurt you by discovering that and leaving. So you will date somebody, quote unquote, beneath you because you will always be more than him. You'll always be the one with the upper hand. You'll always be more than him if he's less than you. And that means you never have to face the scary possibility that someone could truly

see your flaws and all of the things that make you not enough and then ultimately decide that you're not good enough for him. I know it's really tricky, but again, it is super subconscious and happening beneath the surface. Reason number five, you're actually afraid of getting what it that you want. You say that you want love and you think that you want a committed, healthy relationship with intimacy and passion and trust and deep connection emotionally. But deep down, it terrifies you because real intimacy means being vulnerable. It means being seen, letting someone in. And that is so much scarier than dating someone who's emotionally unavailable. Because if you never really have to let love in, you can't get hurt. This is why some women,

repeatedly choose men who aren't capable of deep connection. If he's emotionally unavailable, you never have to face your own fears of intimacy, rejection, or abandonment. So you intellectually think, I want this amazing love, I want the fairy tale, I want the romance, I want this amazing partnership, I want to be seen and witnessed and valued. I want my true equal. I want love in all the ways. I want to be seen and adored and cherished and valued. But, In order to have that, you have to let someone see all of you, and that actually scares the shit out of you. So when you pick men who aren't capable of adult, mature, healthy intimacy, then by default, you don't have to be vulnerable yourself. You're avoiding a situation where you're required to be transparent and visible and face potential hurt.

And here's the truth about this. You may be picking men who are emotionally unavailable, but you, are also emotionally unavailable, avoiding emotional intimacy and connection. But it looks like he's the problem. And all of your friends and family and social media and even your therapist will tell you he is the problem. So I'm really glad we're here today having this honest conversation. Reason number six, you want to feel safe and in control. Dating down can make you feel powerful and in control. If you're with someone who needs you, you feel that you hold all the cards, but really, it's an illusion of control. You deep down think that dating someone who's not at your level means you can just relax because you think you won't be judged or you can't get controlled

by him if your hand is on the button. So it could be that you have a pattern of shrinking yourself, losing your autonomy, giving in, allowing someone else's needs or opinions or wishes or their agenda to eclipse your own. And by being with someone, not at your level, you subconsciously aim to prevent this from happening. Or it could be that you only feel like you can be your true self with a man who isn't your equal, because he won't judge you or reject you. And if he does, it just doesn't matter as much when you don't admire or respect this person, when you don't have high regard for them. You've got nothing to lose when you really don't care so much, right? Whereas a man at your level will trigger all of your not enoughness, and you don't feel like

you can just be your true self. If you have a belief that you have to be perfect to be loved, then picking a man who is clearly not perfect means, ah, I can relax, and I don't have to be perfect either. But here's what actually happens. You end up wasting years on the wrong men, feeling unseen, unfulfilled, and even living with your own truth, that you're lukewarm. You're just half in and half out emotionally. You're not all in because you know deep inside he's just not your person. You know he's not your guy and that you're settling. Finally, the last super subconscious reason that you end up with men who are not at your level, you're lonely. You're starved for love and attention. You've been in a love desert, deprived and parched. Deep down, you have low self-esteem. And so you're easily flattered that this may. You've been in a love desert, deprived and parched. Deep down, you have low self-esteem. And so you're easily flattered that this may, who's handsome or you have chemistry with or who complements you or gives you just the right amount

of whatever it is that you're needing has you sucked in. This is when you become not just a magnet for love bombers, but a target, a sitting duck. You are blood in the water for the sharks. This state of being is a vibe. So you end up taking what you're getting rather than getting what you want. You're not actually doing the picking at all. He is. And he picks. He picks, you so you go along with it. You're only interested in him because of his interest in you. And of course he's interested in you. You're amazing. Even if you don't fully acknowledge this deep in your soul. And at first, all this attention makes you feel so good. But then it doesn't. And once you're in and you do care about him and or he's come to rely on you, it can be very hard to leave. So the bottom

line. Our relationships are a mirror and like attracts light. And the universe does not give us what we want. It gives us who we are. So if you are dating men who are not at your level, it is a reflection of something deeper inside of you that this is how you feel about yourself deep inside, despite all your outward success. You are the problem here, and that is the best news I can give you. Because if you are the problem, that also means you are the solution. The only way to stop all of this stuff, all these patterns, is to work on this relationship with yourself, to change what you think and believe about yourself, to relate to yourself in a whole new way at the deepest subconscious level so you can show up with a new energy

and vibe and then make better choices for yourself. Identity work is the gateway to everything that you want. it always starts with you. This is what we do in the Ready for Love program. We are the leading longest running and most successful and sought after programs in the world for high achieving women who are ready to change their patterns for good, who are committed to doing the work, investing in themselves, and finally getting the love they deserve. I'll put the links in the description so you can check it out. And if you like this video, please give it a thumbs up and share your thoughts with me. Thanks for being here. I'll see you next time.

Thank you.