Uncomfortable Things I Had to Do to Marry Well

I had to go through the worst relationship and breakup of my life to realise the cost of continuing choosing the same type of dynamic. Men who were emotionally unavailable and avoidant, who didn't see me, didn't make me feel safe, didn't treat me with care, didn't show genuine curiosity about me as a person, who raised my anxiety, made me question myself. I learned to trust my feelings and judgments the first time and be ruthless about it.

I had to cut all undefined interactions with men and quit dating for a while. I had to be truly alone, which shocked my anxious attachment system. This was to reset my nervous system and avoid dating for dopamine or escapism. I had to fill my life up on my own and show myself consistently what good, stable love really felt like.

I had to accept I might be single forever and feel genuinely ok about it. If you can't walk away and have a life you love without a partner, you cannot effectively set boundaries and standards. Boundaries and standards only work if you can enforce consequences.

I had to face my own internalised misogyny and misconceptions of love. I had to go to therapy and recognise a man's value should be assessed in relation to me (ie just because a man is successful and attractive doesn't mean he is worthy of my investment - it has to be about the value he actively ADDS to my life) and most importantly, I did not need men's approval.

I had to learn to centre myself and my needs and step into the role of the chooser. A date isn't my audition. A date is me observing, assessing a potential match who can meet me where I am and build a life I want with me on my timeline. I had to realise that expressions of interests and consistent investments are two separate things. I had to see people for who they were and make decisions accordingly, not what I wanted to see.

I had to admit to myself that I wanted love and a serious romantic partner and that my anxious attachment style was part of the deal. While I was in therapy working on it, I could not pretend it did not exist. I had to incorporate my anxious attachment needs into my non-negotiables. It meant I unapologetically looked for a man who wanted closeness and was communicative and consistent. I did not make excuses for bad or lack of communication - I observed and decided accordingly whether to invest or not.

I had to overwrite the "cool girl" programming and stop justifying myself and my dating standards to anyone, especially men who could not meet them. I had to stop making lack of interest and intention about my self worth. I presented myself as well as I could to reflect self respect and where I am in life, but a man's perception of my value and how he treats me is on him. When it matches mine, we can proceed. If not I simply move along. I believed what he showed me the first time. I did not waste time arguing, explaining, fixating.

I had to have conversations about serious topics early on such as life goals, intention to marry, and finances. I would not move in unless we were engaged or at least had a clear plan with a timeline for proposal and marriage. I also had to make sure for any evaluation I had of him, I could recall specific substantial examples to back it up and it had to be demonstrated over time instead of getting swept up by a one off grand (yet empty) gesture or any superficial factor.

I had to communicate my needs clearly once and then make an assessment based on what a man did, not seeing what he did or did not do then justifying his behaviour hoping he would change. If I had said clearly what I wanted and it was not met, repeating it would have only taught him that my standards were negotiable. This required me to be genuinely willing to walk away at any point.

I had to cut contact fully, ruthlessly when something ended and treat the ex as dead. No closure conversation needed, no friendship, no checking. I do not feel bad for these men. When I'm out, I'm out. I had to understand my attention and presence has value and I do not spend them mindlessly.

I had to recognise that being respected by a man matters more than being liked by him. I had been conditioned to soften, smooth over, laugh things off, because being liked felt safer and momentarily more rewarding than standing up for myself and calling him out. But the truth is, the more I cared about being liked by a man, the less he respected me. If I let small disrespects slide to keep the peace, I was teaching him that he could get away with it and he would with more. Disrespect that goes unchallenged does not stay small. It becomes bad treatment and resentment, and eventually abuse.

I had to recognise that 1) any urge to use "games" or act defensively (ie delaying text messages on purpose) came from a place of hurt and self protection, and 2) a man who is interested, intentional and emotionally healthy won't make me feel like I need to do it. I myself had to be ready to date and hold my frame, ie acting like how I would expect an interested, ready for marriage individual to act, and being stable and consistent at that. Then I could observe him and see whether he could meet me there. Men will self select themselves out quickly.

I had to stop trauma-dumping and oversharing or talking about myself negatively especially early on. It is my responsibility to put my best foot forward, protect myself, and communicate intentionally to connect, not to process one sided through another person. I had to avoid handing the map to my rawest places to a stranger who has not shown me if he could handle them or how he would handle them (ie he could use it to show me exactly what I wanted to see vs who he really is.) I had to understand when to share what, at which level of detail or depth, and for what purpose.

I had to stop asking "why did he do that" and start asking "what am I going to do about it". I would never know why and it wouldn't change what he already showed me about his interest and intention. I learned that I do not need to understand a man's psychology to make a decision about him. I only need to know how he behaves and how it makes me feel, and act accordingly.

I had to stop relying on men to do the right things for me. The reality is most people don't have your best interest in mind, they have theirs. If you let someone waste your time, they will do it. When a man strings you along or breadcrumbs you or confuses you in any way, the simple reality most of the times is he does it because he can. It's on you to say it is unacceptable and do the right things for you - cut your losses. And do it ruthlessly.

I had to take men seriously the first time they told me something about themselves that did not work for me. If a man tells you early on that he is "bad at texting," that he is "not really a relationship person right now," that he has commitment issues, he is offloading the guilt of knowing he is wasting your time, he is managing your expectations. He is telling you who he is so that, when he behaves this way later, you cannot say he didn't warn you. A man who is serious about you wants you to see him in the best light. He does not volunteer things that would make you walk away. So when he does, run.

I had to stop rewarding and engaging with low effort or unwanted behaviours. A text of any nature after 10pm got a reply the next day at a respectable hour, if at all. A long absence and a sudden reappearance got nothing. I did not waste energy explaining to a man why his behaviour was a problem, because explaining is labour and a reward - it tells him I am still engaged, still emotionally invested, still trying to fix something with him. I let my behaviour communicate everything I needed to communicate. The invested men adjusted, repaired appropriately. Others removed themselves, which was also the right outcome.

I had to be the one who set the pace of the relationship and avoid just going along with his. If I was not ready to have sex, I had to be an adult about it and avoid situations that could lead to it - late dates, alcohol, going back to his place. The point is not to have sex and then try not to get attached. Getting attached after sex is healthy. It is how the human body is designed. It is about making a conscious choice about who to get attached to. It's a matter of long term wellbeing especially with anxious attachment. That meant only letting it happen when I felt fully ready, with a man who had already shown me he was invested and bonded too, not just attracted. The right man will respect it.

I had to let go of the fantasy that a man will save me and trust that I know what's best for me and can make good decisions for myself. Instead of getting fixated on a man's job title, wealth, appearance, I had to lead with my strengths and core values and evaluate men by the same things. It sets the foundation to build a relationship with real substance and compatibility, where you can hold your own. Anything else (wealth, lifestyle etc) is the byproduct on top. You can disagree, set boundaries without fearing his reaction, and walk away without losing yourself. A relationship where you are relying on a man's mercy for your real security is not a partnership. It is a position.

I had to accept that if I was asking myself whether a man was interested in me, the answer was already no. An adult man who is interested in you does not let you wonder. He texts you, plans the next date before the current one ends, introduces you to his friends, brings you into his life. The whole question of "is he interested" only comes up when his behaviour is ambiguous, and ambiguous behaviour is the answer. There is nothing interesting or mysterious about hot and cold behaviours. It's simple - they are designed to stop the relationship from ever progressing passing all the cost and labour to you.

I had to accept that the power dynamic in a relationship with a significantly older man as a young woman in my early 20s would be structurally skewed against me, and no amount of maturity on my part could fix that. He has the career, the money, the social position, the systematic advantages. As a young woman, you don't. That gap is not romantic. It is a power imbalance that will shape every decision in the relationship — whose career gets to be prioritised, where you live, whose timeline you follow. And there is not much you can do about it. To bridge the gap, it is always you who has to adjust to fit him — accelerating your life, performing maturity you do not have, pretending to be ready for things you are not, suppressing the parts of yourself that do not match where he is. You cannot be true to yourself in that relationship, because being true to yourself would mean naming the imbalance. And you would be too attached to risk doing anything to lose him. Instead you shrink and become a shell of yourself, increasingly dependent on him. It's the breeding ground for abuse.

I had to recognise that a significantly older man is not interested in me because I was "mature for my age" or because I was "intelligent." He is interested in a significantly younger woman because they are young, attractive, boost his ego, and are inexperienced enough to overlook things a woman his age would not. Telling you you are wise beyond your years does the job because young women, especially those with troubled childhoods and attachment issues, are starved for approval, and he knows it. If you were as smart as he says you are, you would already see through him. He is counting on you not seeing through him.

I had to stop looking for the parental figure I never had in a romantic partner. You're not going to find it there, especially with significantly older men, when you feel intensely drawn to him because of the age gap specifically. It's a sign you have healing to do. He might be as old as a parent but he is not your father. He does not have caring responsibilities for you. He does not love you "just because." He is not safe. You cannot rely on this man to do the right things all the time. The wound has to be healed somewhere else, not by a man who benefits from you being unhealed.

I had to let go of the idea that I was the exception and start operating like the rule. In an age gap dynamic, he has more complex psychological patterns, defences, manipulation tactics. As a young woman, you are not equipped to handle them. You do not have the financial independence to leave easily if it goes wrong. You do not yet have the boundaries and standards that come from going through life on your own building your own security. This is also how you get gaslit and made to feel crazy because you simply have not seen any better to compare it to. You might even hide the relationship from friends and family because of the stigma, which leaves you more isolated, which makes the gaslighting work even better. He knows all of this. The asymmetry is the point.

I had to face that the relationship is set up to fail. The early months will be smooth, that is the part where the gap feels exciting and the differences feel like depth. But in five or ten years, you will not be the same person. He will be set in his ways, and you will be growing rapidly through the years that change a woman most. The two outcomes are: he will stunt your growth and damage you in the process, or you will outgrow him and want to leave a relationship you never should have been in to begin with. Either way, you will spend your twenties, the most transformative years of your life, paying the cost of a decision you made before you knew what you were choosing. And the damage does not end when the relationship does. A bad relationship with a significantly older problematic man can wound you for years afterwards and leave you with a distorted view of what love, intimacy, and partnership are supposed to feel like. Those years are not refundable, and neither are the ones spent recovering from them. No matter what you think he can provide you, he will always take more and the cost is not worth it.

I had to accept that as someone with an anxious attachment I could not keep jumping from one dating situation to another, finding the next relationship to regulate me only to be left even more damaged and anxious again. I had to break the cycle and take time to really tend to myself first. I had to accept that it'll be really uneasy at first when I had no one to attach to, nothing to obsess over, but once I let myself sit with these feelings, they would pass and I'd eventually realise I was fine. I could meet my own needs. I could be ok on my own. And that's the ground for me to set up boundaries and standards because I knew I could walk away, back to myself, and I'd still be fine.

I had to be upfront about my need for closeness and emotional availability instead of trying to play it cool. When you have an anxious attachment, the instinct is to hide it - act unbothered, send delayed replies, pretend you do not care as much as you do - because you have learned that showing your needs makes men pull away and it can really hurt. But it's actually the right outcome because that shows you they can't meet your needs and you wouldn't want them anyway. Showing your needs just filters them out more quickly, saving you time. You don't shrink yourself just to be in a relationship; you find a relationship that can make space for the whole of you, that can help with your anxiety not worsen it.

I had to recognise my anxious attachment doesn't make me less worthy, it isn't my fault, it's all the more reason I should love and protect myself harder. With anxious attachment, every date and every uncertainty costs you more than it costs the average person. Your anxiety is the price you pay every time you take a chance on someone. So you have to make sure the man is really worth it. He has to be someone who is secure with himself, fully available, and sure about you. And you cannot afford to choose any less. I had to trust my anxiety and understand that when dating a man makes you more anxious it is enough of a reason to step back, not trying harder.

I had to build a life I genuinely loved before I let a man into it. When there is nothing else holding your attention, every text, every silence, every ambiguous look becomes the whole world. I had to fill my life up so that no one could occupy all of it. With anxious attachment, you can be overly focused on whether he likes you, whether he is pulling away, whether you're doing enough to keep him, and forget you're here to pick a partner for you and your judgment matters, too. So by having a life you love, you stop needing him to be your everything and it allows you to ask for what you need without the fear of losing him.

I had to accept that I'm not an avoidant person, I could not date like I don't care, I could not date casually because there's my wellbeing literally on the line. I had to take responsibility for managing my own anxiety and set rules to protect myself. For example, not have important conversations in messages, not put myself in situations I know would spike my anxiety, not engage in casual sex, take time to get to know a man in different settings over time, not going back and forth with an ex. I had to put my anxious attachment first and make decisions to prioritise my wellbeing. The right partner would understand and respect it.

I had to accept that the dating pool has plenty of low-effort people and stop making each one into an energy draining event. A man who matched and never said hello was not a story. A man who suggested a last-minute date or texted at 11 PM was not a story. None reflected on me. They were all the same data point: not him, move on. It is okay and healthy to feel disappointed, hurt, or to give yourself time to recover, but I had to stop giving strangers more energy than they had earned. Most men are not the right one, and that is exactly what the dating process is for: selection.

I had to forgive myself for all the times I failed to enforce my boundaries or standards or didn't even know what they were. I knew why I did what I did and gave myself compassion. I had to step into the new identity of someone who knows her worth, who can protect herself, ask for what she wants and get her needs met. Someone who is not afraid of letting go, who knows the costs of staying. I did not care what happened or who I was in the past. I acted as this identity until it became the new default. I built trust with myself. It was how I put myself out there again after failed relationships and believed I deserved to ask for what I want.

I had to understand that the beginning of dating is when you shape the dynamic of the relationship. And it is incredibly hard to change later. A man who finds a relationship comfortable as it is has no reason or incentive to renegotiate it. If he is not putting in the effort to plan a date now, he is not going to magically become someone who buys the ring you love and plans a proposal later. Even if he does propose, the daily life would still be the version that didn't plan a date. So if you go with the flow and tolerate things you do not actually like at the start, you will end up in a relationship on his terms, one where you keep absorbing the cost.

I had to understand that women and men do not arrive at dating on equal footing, and that the asymmetry is not in our favour. Women are conditioned from childhood to accommodate and be liked, while men are conditioned to assert their preferences without the expectation to accommodate. What this means in practice is that you have to know your bend reflex is there and consciously resist it while actively prioritising your wellbeing, setting boundaries and standards. Date as someone evaluating a serious offer, with terms and conditions to be set, not as someone hoping to be picked.

I had to keep doing the work even after the dynamic was shaped. Standards and boundaries are not a one-time conversation. They are a thousand small moments where you choose to say something instead of swallowing it. Where you reject a behaviour the first time it happens, not the tenth. Where you stop gaslighting yourself and minimising how you felt. Asserting your needs is a muscle, and like any muscle it gets stronger the more you use it. Every time you speak up, the next time gets easier.

I had to stop assuming a man thinks and behaves the way I would. Most of women's disappointment often comes from expecting the man to do what you would have done in his place, then feeling let down when he did not, driving yourself crazy with all the why's. But he is not you. He does not bond the way you do, and he might not value what you value. So you have to treat him as a completely new, separate person and observe him instead. People tell you who they are and how they see you all the time — pay attention.

I had to think critically about the love stories I grew up on, the romcoms and dramas that shaped what I thought love was supposed to look like. You're taught that a man's good look or wealth automatically puts him above you and makes his attention something to feel lucky to have, and a power imbalance between a man and a woman is romantic. The box is already drawn for her as she's written small, with no room to be a full person. I had to recognise that the same value system is built into almost everything, and actively fight it in what I assign value to and in my own biases. I could step out of that box and ask for what serves me as a whole person.

I had to decentre my relationship status. Being single and being in a relationship are simply two different states of being, not a comparison where one means you succeed and the other means you fail. A relationship is supposed to add value to a life you have already built, not be the prize that makes the life worth something. What you centre is your own wellbeing and being your best self. It means if a relationship doesn't make you healthier, better, or it does but then stops, you get to reevaluate and make a decision at anytime.

I had to actively override the conditioning to please and to be liked. Saying no and drawing a boundary does not push the right people away. Healthy people understand boundaries and expect them. It builds trust with them. When someone knows where you stand, your yes means yes, and no means no, they know how to be around you, and they respect you more for it. The people who get put off by a boundary are those who want you as a function, not a person.

I had to believe the relationship I wanted existed even before I had any evidence of it. I had to show myself what healthy good love looked like through how I treated myself. I had to carry myself like it's already mine and the right person would be lucky to be with me, not someone I would be grateful just to have.

I had to take the first few months seriously, because that is when a man is most incentivised to show you his best while learning how to operate with you. So if he is already inconsistent, careless, or hard to pin down this early, it is not going to magically get better, and if you let it slide, he's learning how little he needs to put in to keep you around. You can enable low effort by tolerating it, but you cannot force high effort out of someone who will not give it. When you set your standards and he does not respond to them, that is not a loss or a sign for you to want less. It is your standards working exactly as designed: he has selected himself out and cleared space for the right man to show up.

I had to relearn what "high value" means, because I had it backwards. I used to doubt myself and get carried away when meeting someone who seemed attractive or successful with a big job title — I thought his attractiveness and success automatically made him "high value" and I became the chaser, proving my worth to him. But value to whom? Such value had to be judged by me in relation to me and my life over time. By this definition, you have no way to determine if someone is "high value" or not after a handful of dates. That's how you'll stay grounded as a chooser, and not overlook red flags or tolerate bad treatments.

I had to understand that a man becomes more invested through what he does for you, not through what you do for him. So every time you over-give, or make yourself useful to win a man over, he doesn't want you more; he's learning that he can do less. If you want to give, there is plenty of time for that later, once you are officially together. You are already conditioned and set up by the system to give more anyway (e.g. household work, being paid less.) So the only way to make sure you gain from a relationship, and to read his intention and commitment, is to observe him, leave space for him to show up, and look for real effort and investment from him upfront.

I had to accept that there is no winning with an avoidant or emotionally unavailable man. There is no version of you, no amount of patience or understanding or proving yourself, no amount of waiting when to have sex, that turns someone avoidant or unavailable into someone who can be close. His avoidance is never about you or your worth; it is about his own limits, and nothing you do could reach inside him and change that except for him wanting to do it and actually doing it in his own time. The only thing that ends the cycle for you is leaving it and choosing differently.

I had to remember that a man is only as special as you decide he is. When a relationship doesn't meet your needs, or when he doesn't choose you for any reason, you can take that specialness away and shrink him back to the person he is with flaws and limitations like everyone else, a person who isn't compatible with you. His opinions of you are only one person's view and ultimately no longer matter. No man who isn't here with you and doesn't choose you is that special.

I had to base my value system on my own strengths, not on the things I do not have. For example, if you are not wealthy, it does not serve you to internalise a system that measures people by wealth. You have put yourself at the bottom of your own scale and handed the power to whoever holds the thing you lack. So you measure by your values and strengths, and you assess men by that. Then you decentre beauty, age, and male approval to take back the power; your sense of value won't depend on metrics society will always use against you, and so you date from a position of leverage rather than need or seeking validation.

I had to stop choosing men primarily by external markers of success. When you pick mainly on money and status, you get men who tie their identity to their jobs, who are too busy, who hold sexist views, who think highly of themselves for having money, or who simply do not value you as a person. So you lead with your core values and strengths and needs and stay discerning and ruthless no matter how successful he is. In fact, the more successful he is the more discerning you should be since with money comes options and power. If you invest in yourself and use yourself as the measure, the man on your level will likely be solid too. That's also how you can act as their peer.

I had to be honest with myself and think clearly, instead of wishfully. So you look plainly at what you are doing with this particular man, and ask the real question: as it stands, is this really going to lead to the relationship and the life I want? And if it does not, what would have to happen for it to be? How realistic? And what is the cost of continuing? Look at the evidence, not just feelings. You can feel all you want but intense feelings on top of the wrong structure are a costly trap.

I had to ask myself why I wanted to be married at all. Many people treat being married as the goal in itself, so they chase the status of marriage rather than a particular life with a particular person. Once you are clear on what you want from a marriage, the kind of man you need becomes obvious. You are looking for the person who fits the life you want, rather than building a life around some man you're fixated on, which might not have space for the whole of you or support you long-term. And marriage itself is not a fixed thing you step into. You have agency over what it becomes. Challenge every "it's just what a marriage is".

I had to operate on probability rather than hope or fixed rules. Probability means you understand which actions and situations tend to lead to which outcomes, and what a given piece of information is likely to tell you. You observe, you collect data, you make informed inferences, and you decide at the point where waiting for more would not add clarity. This approach also stops you taking things personally, because data sits outside you, as information to read, so it has nothing to do with your worth. It also means building guardrails to lower the risks you can, since you will not know everything. And when something unwanted happens, you know there was always a chance, instead of blaming yourself for not having known better.