The Hilary Silver Podcast - #104: The 3 Stages of Relationships—And Where You're Secretly Struggling

Episode Date: February 20, 2026

You can be brilliant in every area of your life and still feel lost in love if you do not know which stage of relationships keeps tripping you up. Hilary breaks relationships into three defining stages and asks a direct question at each one: do you trust yourself here? From choosing the right partner, to staying grounded in the early months, to sustaining a healthy long-term bond, she challenges the idea that love problems come down to luck. If you cannot trust your judgment, your authenticity, or your ability to handle intimacy, the same patterns will follow you into every relationship. She walks through the most common blind spots women have at each stage: ignoring red flags, performing when you really like him, over-functioning or shutting down once things get serious. Most women were never taught the actual skills required to build lasting partnership, yet they assume desire alone is enough. The deeper invitation of this episode is honest self-assessment. Where are you unsteady? Where are you unskilled? And where are you hoping the right man will compensate for something you have not yet strengthened in yourself? Episode Highlights: How to know if your picker is broken The difference between standards and fear Why the early dating stage exposes your deepest insecurities The hidden skills required for long-term partnership How lack of self-trust fuels repeated relationship patterns Episode Breakdown: 00:00 Understanding Relationship Challenges 05:55 The Picking Stage: Trusting Your Choices 12:08 Navigating Early Relationship Stages 16:55 Building a Lasting Relationship: Skills and Confidence ✨ 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. ✨ Ready to stop repeating the same patterns and finally create the love you deserve?  🎯 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 Self-Centered Bundle: Built to Support the Real You Three intentional programs that work better together, plus The Daily Journal. Find it here!

I know because you're listening to me that you're smart and more than capable in so many areas of your life. And if at the same time your love life is disappointing, unfulfilling, or non-existent, today's episode will help you see where you're stuck, whether you're in a relationship or looking for love. I'm walking you through an exercise that will help you get clear at what stage of relationships you're having the most trouble so that you can see clearly what's been holding you back and to know exactly what to do to finally create the loving, fulfilling relationship you desire. And make sure to stay till the very end because I'm giving you the ultimate solution for all women to get exactly what they want in their loving relationships. Hi, it's Hillary. Welcome to the Ready for Love podcast.

Okay, so this exercise I'm about to walk you through is a very very, very good. over simplified breakdown of three stages of relationships, just to make it easy for us to see what is the hardest part for you, where your obvious obstacles are, and where your blind spots are too. This is about awareness and is not to make you feel bad or to create a problem where there isn't one. It's just simply a way to consider all the many things that are going on and happening as you are in the process of getting into the kind of loving, supportive relationships. that you want with a kind of partner that you want. Yes, there are lots of other things to consider besides what we're going to go over today. But this is going to help so much in seeing the obvious

troubles and obstacles as well as revealing the blind spots, as I said, because blind spots are very dangerous. This is when you are thinking that you're good at something when you're actually not. And that means that you're just going to keep doing it, but it's not really having the effect that you're hoping that it will, and it could even be causing trouble. And that's when women really get in their own way and don't even realize that they are actually their own biggest obstacle. And by the way, that is one of the biggest benefits

of having a coach for any area of your life, someone who actually cares enough about you that they will point out the things that either no one else can see or who are just not willing to tell you. Feeling better is temporary, but being better and doing better is actually what creates real permanent change.

So as we go through these, just really reflect on what I'm saying and be honest with yourself. Maybe you're just having trouble in one of these stages, and maybe it's a little bit of all three. So here we go. The first stage is the picking. How confident are you that you can trust your picker? Do you have crystal clear criteria for your ideal man? That is, do you know your requirements, your must-haves and your deal breakers? And this is more than just a list on paper. It's actually recognizing it in real life when he's standing

right in front of you. Things don't always look and feel like what is written on paper. It's kind of like when the GPS is telling you to turn right, but as you're driving, there is no place to turn right. It's kind of like that. Lists don't always translate to real life presence or behavior. And these criteria cannot just be that you want to have the same lifestyle, that you like the same things. It's so much more than that. It's values-based criteria that actually really matters. Also part of the picking, do you see the red and the yellow flags and walk away? Or do you ignore them and minimize them and rationalize them? Sometimes people see the red flags and they go, I'm in. Jump right into the arms of a man who is a walking red flag. Do you tell yourself, nobody's perfect. Maybe I'm just being.

too picky, I'll just give him a chance. So you end up giving him the benefit of the doubt while you doubt yourself. So can you trust your intuition and trust your gut that if something seems off, you actually listen and don't bypass the warning indicator signs despite what he looks like on paper or if he checks some of your boxes but not all of them. Do you refuse to settle for less than what you want, no matter how much you want a relationship, or do you negotiate with yourself, lower your standards, and make excuses for why he's good enough? So here are three things that I see all the time. First, women who ignore red flags because they like the idea of the relationship rather than seeing it for what it is, or they like the idea of him rather than seeing him

for all of who he is. They want so badly for this to be the one, because you know, because on paper things seem great or there's chemistry or they just don't want to start all over again and they can finally just not have to date anymore. I also see women who settle because they're afraid that they won't find anyone better and think maybe this is just as good as it gets. I see women who doubt themselves. They think maybe I'm just too critical. Maybe I'm being too picky. Maybe I should just give him more time. Second, I see women push men away too soon. They're scouting out and creating red flags where maybe there aren't any because you're on the lookout. You've been there, you've done that, and you are not doing it again, so you're hyper vigilant. You think that

you can prevent disappointment or disaster by scoping out all the potential problems early on. So the first sign of something, you're out. You cut and run. Or finally, you're not even picking at all. For two reasons. The first, you're letting him do all the picking, and you're just passively going along with whoever shows interest in you, meaning you're interested in him only because of his interest in you. Take that in. That means that you end up taking what you're getting rather than getting what you want. Or the second reason you're not picking at all is because you've just opted out completely. You're taking a break from dating in relationships or you're just giving up on it all together, trying to accept that maybe just love is impossible for you, that you can have all the other

things in life, like work and friends and a great lifestyle, but the love thing, it's just not the part of the plan for you. And so you convince yourself that you're just too busy or you're too content on your own, you just don't need a man. That's a lot. I know. It's a lot to consider, and it's a lot to take in. And I suggest you actually go back and re-listen or re-watch that just so you can absorb it all. Those are all picker problems. and if you can't trust yourself to choose the right man for you, you're going to keep ending up with the wrong men or no men at all. So again, I ask, how confident are you that you can trust your picker? If you're not entirely like a hell yeah, I can trust myself, then you have some work to do.

Okay, so the next stage is the early tender stages in those first six months or so, sometimes longer, but this is when it's exciting and scary and sexy and anxiety provoking all at the same time. We all know this feeling. It's intense and fun and titillating, but it can also bring out the crazy in all of us. So how confident are you in these early stages that you can just show up easy, breezy, comfortable in your own skin? You are completely authentic being your true full self. You're not guarded with a wall up in protection mode. you're not waiting for the other shoe to drop. You're also not pleasing or accommodating and overgiving or bending trying to be whatever

you think he wants you to be. So you're remaining true to yourself the entire time. You're also not anxious and overthinking every text. You're not performing and contorting yourself and sharing only your best parts of yourself. And as you are your real relaxed self, you can easily navigate the texting and the messaging and the messaging and the flirting and the pacing, and as things start to become real, you can keep the attention of the really quality men that you're excited about just by being your real self and quickly exit when it's the wrong guy without feeling bad about it or second-guessing yourself at all.

Or do you get anxious? Do you start spiraling? Do you lose yourself trying to make him like you? This is honestly where things go sideways for so. many women. It's easy to be confident when you don't like him, right? Who cares? And it's the men you don't like who end up pursuing you. Take this in. The men that you don't like end up pursuing you. It's not so easy when you do like him and when you get excited about him and you want him to like you. It's not so comfortable when things go beyond the first date and things start to get real

when you're invested in this working out, when you catch feelings and you want him to like you. When you get this part wrong, this is where the pattern happens of only the men that you're not interested in pursue you, but the men that you are interested in don't. It's super frustrating and disheartening. And it's when you get a few weeks in or a few months in and it fades, it fizzles, or he just outright ghosts. So here's what happens for most women in this stage. They start performing. They bend themselves into a pretzel trying to be the woman they think he wants. They bite their tongue.

They go with the flow. They hide their needs because they don't want to scare him off. They overanalyze everything. They crowdsource opinions from their friends and their therapist and their dad. They Google. What does it mean when he? Trying to decode his behavior. They get attached too quickly.

They start imagining a future together after one good date. Or they go in the opposite direction and they shut down and they put up their walls and they protect themselves so that he can't. get close. And either way, the women are just not being themselves. They're operating from fear, from insecurity, from a desperate need to be chosen, and men can feel it. So, again, that was a lot. How confident are you on a scale of 1 to 10 in those early stages? There's a lot going on there. If you're not 100% confident, then you definitely have more work to do. And finally, The last stage. How confident are you that you have what it takes to create an adult, healthy, mature, loving relationship and make it last for the long term? You feel both worthy of this kind of

love, which means you know how to receive it, and you feel capable of it, having the tools, the skills, the knowledge, the awareness to actually do it. Do you know how to be vulnerable? Do you know how to communicate your needs, how to navigate conflict, how to fully express yourself, how to maintain intimacy and passion over time, how to navigate issues around power and control, how to trust someone and really let him in? Do you know how to stay true to yourself while you're also in a partnership with someone else? Or are you afraid of messing it up again? Or ending up in another relationship just like those in your past, repeating patterns of dysfunction, and disappointment. Here's what I hear from women all the time. I'd like to think I could do this.

I'm reasonable. I'm loving. I make a great partner. Of course I can do this. Or I want this, so yes, I'm ready for it. But I want to push on this a little bit because this is where most women have big blind spots. For most of us, the reality is we learned what we don't want from our parents. Maybe your model really sucked. And even if you were lucky enough to have parents with a great relationship, I guarantee you, they were not teaching you how they were doing it. They weren't saying see kids, did you see how he just handled this conflict and mom apologized and dad? Did this? No, that's not happening, even in the best houses with the best model of relationships. And we don't learn this anywhere in school or therapy or religious institutions along the way. And likely you've

just not been successful at it in the past or you wouldn't be watching this video or listening to this episode. Even if you have had a long-term relationship in the past, it doesn't necessarily mean you can do this confidently because if you show up in your next relationship the same way that you were in the last one, you're going to get more of the same. You were part of that dynamic that didn't work before. You can't show up in the same way in your next relationship and expect to have a different experience. And having long-term friendships is not the same. Do not be fooled. So here's the thing. Wanting love and having the skills and the know-how to do love are not the same thing. Here's what I know to be true. You cannot fully thrive in your life

if one area is growing and the others are quietly being neglected. Eventually the imbalance catches up to you. That's why I created three programs to support women in the areas that matter most. Self-devoted helps you reconnect to your body, your health, and and your self-care. Self-satisfied helps you create relationships that feel secure, fulfilling, and aligned. And self-made helps you shift your money mindset so wealth not only feels possible, it feels inevitable. These programs are not random. They are intentional, and when they are done together, the impact is powerful. When you choose the full bundle, I include the daily journal. This is a practice I use myself, and it's the tool that helps you apply what you're learning

every single day, so change becomes real, not theoretical. If you're ready to invest in yourself in a way that actually supports your whole life, go to Readyforloveink.com forward slash courses. You can explore the programs and the bundle at Readyforloveink.com forward slash courses. One of the ways I've been upgrading my life lately isn't through big changes. It's been through small ones that actually add up. I started noticing the places where I'd gotten complacent, especially with bras and underwear. Wearing things that looked worn out, didn't fit that well, or just didn't make me feel great.

but I kept wearing them anyway because, well, they were just there. And once I noticed that, I couldn't unsee it. So I started paying attention to the things I use every day that I have a clear preference for, and then I decided to replace the rest with the best. That's where the fit everybody collection from skims comes in. The t-shirt bras have underwear that supports without cutting in, and they make me look smooth and lifted in all my clothes. And the thongs are both invisible and comfortable, the kind I forget I'm wearing in the best

possible way. It's an easy upgrade, but it changes how my day starts. even if no one else sees it. And if someone else does, well, that's just part of being well-dressed. Shop the Skims Fits Everybody Collection at skims.com. That's sk-I-M-S dot com. After you place your order, let them know we sent you. Select podcast in the survey and choose Ready for Love in the drop-down. So all of this to say, it makes perfect sense if this is hard or scary for you. Of course, you're scared. Of course you doubt yourself. Of course you wonder if you're going to mess it again. Here's what usually happens. Women end up over functioning. They take care of everything.

They manage his emotions. They lose themselves trying to keep the relationship afloat. Or they shut down. They can't be vulnerable. They can't let him in. So they protect themselves because that's so, that intimacy is just so intense and makes it impossible to experience it. Or they sabotage it. They pick fights. They pick him apart and find faults. They pull away. They unconsciously push him away. because deep down, they don't believe they deserve to be loved and they are scared of it. So here's the question again. How confident are you that you feel fully equipped to have a healthy long-term relationship and make it last? If you're not 100% sure that you can do this, you have work to do.

So remember, this exercise isn't about making you feel bad. It's designed to help you see where you are having the most trouble so that you can get the support that you need. This is ultimately about being able to trust yourself to navigate each stage of a relationship, knowing what is best for you and doing it, even when you really like him, even when you're scared, and even when you really want it to work out. Most women don't trust themselves when it comes to love and relationships because they've never learned the skills and they've never been taught the skills. They've never practiced the tools. They've never seen themselves successfully navigate a long-term healthy relationship. So they're trying to do something

with their eyes blindfolded and their hands tied behind their back, something they don't know how to do, hoping they'll just figure it out as they go. And it's scary when you don't know what you're doing. And so much is at stake, your heart, your safety, your sanity, your well-being, sometimes even your livelihood when you start thinking about merging your lives together. But you can't build self-trust by winging it. You build trust by learning the skills, practicing them, and witnessing yourself doing it. And above all, by knowing you will always do what's best for you even when it's hard. That's when everything changes. When you trust yourself at every stage of the relationship, when you trust your picker,

trust yourself to just show up authentically all the time no matter what. And you trust yourself to build something real. You stop repeating these painful patterns. stop attracting the wrong men and you stop sabotaging the good ones and you start showing up with clarity and certainty, free and clear to just let love in. And that's when you finally attract the extraordinary partner that you've been waiting for and longing for. So the work isn't about finding him. Because even if Mr. Wonderful came knocking on your door right now, if you don't fully trust yourself at each stage, it's not going to work. It just won't. And it's not about being perfect either.

It's about stepping into the version of you who feels 100% worthy of the kind of love that you want and capable of making it happen. That is your relationship with you. It always starts with you. I do want to say, Ready for Love really is the absolute best in the world for helping women with all of this, the deep psychology and the relationship skills. So if this episode resonated with you, apply to speak with us at ReadyForlove.inc.com forward slash apply.

We'll have a deep conversation with you to assess exactly where you're struggling and give you a clear roadmap for what to do next. Or check out our online classes at readyforlovingt.com forward slash courses. Thanks for listening and see you next time. And if you are watching on YouTube, please leave some comments. Let me know what stage you're struggling with the most. I'd love to hear from you.