The Do’s and Don’ts of hypergamous dating .

Celine Gray
12 min readFeb 9, 2023

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Hello ladies,

I just wanted to drop a quick piece of advice that turned into a long article (sorry).

In order to achieve anything in life, we must have clarity of our goal in order to make the right plan, then we need to develop a strong sense of discipline and the ability to not get distracted so we can achieve it. Financial success through hypergamy is no different.

But the unfortunate thing is that we don’t get granular about it, we don’t analyze the small details and factors that play into it. Sometimes it’s because we feel a little shame to look at human connections and relationships in such a dry way. But it’s a necessity.

From interacting with many young ladies over the last few days, I realized that there is an important aspect that some are missing from the picture.

It’s the emotional intelligence and mental strength to not fall for distractions, the power to control and regulate your own feelings and emotions, and the capability to shake off anything that is not aligned with your purpose as a woman who is on the prowl (don’t roll your eyes) Most women who have accomplished financial success through hypergamy intentionally know it’s a prowl, they don’t admit it to people because it’s demeaning in our modern culture.

Please keep in mind these are all skills and subtleties that you learn and master over time, don’t be too impressed by other women, no one is born with complete knowledge and a clear map of what to do and how to act. And don’t beat yourself up for your missteps, observe, learn, and improve. I learned a lot the hard way so be kind to yourself and be grateful for your mistakes, just don’t repeat them

In matters that are not tangible and palpable (like human relationships) it’s hard to see how these skills manifest, so here are 10 clear examples:

  • When you meet a man you like but doesn’t meet your financial standards. Don’t go out with him, and don’t entertain the thought of it because we are humans and we catch feelings, and admitting to ourselves our own humanity and vulnerability will save us from a series of bad decisions and heartache. Consider yourself the bar exam, if he doesn’t get the passing score he is not qualified for the following interviews. It’s harsh to say, but this is better than getting emotionally attached to the wrong person and spending years being unsatisfied and making him feel small (men feel things too even when we try to hide it). To do this, you need to be in full control of your emotions and be okay with the momentary feeling of discomfort (just like you are with the cookie box, you don’t bring it to your house and challenge your willpower, you just leave it in the store)
  • You are dating a man who’s gotten the passing score for the interviews (ok I love analogies), now you’re in the early stages of dating but he is not meeting your expectations (no matter what they are as long as it’s realistic and specific to you). Stop dissecting his messages, stop looking for clues, don’t drop hints (men nowadays notice all of them), stop trying to psycho-analyze him and find his love language (there is no love to be communicated yet) or his issues, stop overthinking it, stop trying to teach him or guide him (when a man doesn’t love you and trust you for a significant period of time, he is going to hate being told what to do by you). Just find the strength and discipline to move on, make it quick, make it clean, and don’t look back. Successful men over 30–35, in whatever field they are, know what to do. If he has watched one rom-com in his entire life, he will know what to do, if he doesn’t know but care enough, he will eventually find out what to do (because this type of man gets what they want). So if he’s not meeting your expectations, it’s because he doesn’t feel the need to or doesn’t want to (I Am talking early stages of dating). Be brave to face the harsh truth, shake hands and move on.
  • Do not put yourself in situations where you might end up doing things you don’t want to do. Stick to the rules you set for yourself and be disciplined about it. Back in the day before laser hair removal and before I developed a strong discipline, I would keep myself ungroomed down there on purpose so I know I will not be dropping my panties under any kind of circumstances (mind you I am middle eastern so you get the image) and sometimes even my armpits when I know I shouldn’t be taking anything off. Same with alcohol, before any date, I would make important appointments early in the morning so I don’t drink more than 1 glass of wine, that way I keep my composure and I’m sure I don’t say or do things I will regret. I also always set a timeline in my head, the date starts at 8 and finishes no later than 10.30. End of the story, I don’t try to talk myself out of it no matter how good the date went. And if you end up doing something you regret, move on, don’t try to fix it don’t explain yourself to him, just learn from it. You’re most likely not going to be able to repair or change the impression you made. (Quick story time, in my 20’s I got drunk and I really messed things up, I acted like a sloppy undisciplined lady. I tried to go back to my sober composed self after that day and keep being the lady I wanted him to see me as it didn’t work. It never works, he is entitled to think of you however he wants, don’t try to rebrand yourself or change his mind, he is not going to, don’t waste time trying (successful men are quick to judge and compartmentalize), so the best thing in these situations is to stop seeing him and just move on without looking back.
  • In the early stages of dating resist the urge to reveal a lot of yourself, learn how to build suspense, and cultivate his eagerness to discover who you are. Be in control of your narrative, men pay attention to everything. Even more when you feel a strong connection and, in your head, you think he is your soulmate and you can’t wait to tell him all the things you think you have in common. Resist the urge to call and text unnecessarily. Resist the desire to tell him your life story and all about your day. Do not answer phone calls or texts after curfew, mine is always 10 even if am out partying, first, you should know that it’s inappropriate to reach out to you that late when you’re not even in a committed relationship. If he does, you answer kindly in the morning, he’ll get the message and he will never repeat it as long as you don’t budge.
  • If you like him and you’re considering a serious relationship with him, do not drop hints about gifts, do not suggest shopping, do not talk about your or his finances and money, and do not share your financial struggles with him(even if he asks), this is early in the relationship and rich men see you coming 10 miles away and they will even try to pull out answers from you. He is a grown man, probably smart, and he knows what to do, if he wants to give you something or offer you a gift, he will do it without hints, (I’ve seen men give significant gift cards from nice clothing stores because they invited the woman they are dating on a trip and they know we love and need shopping before a romantic getaway) Keep your material wants to yourself, you’re not fooling him he is just playing the game because he has an agenda. This is not bad in itself, just don’t do it with men you like and consider for something durable and serious. Always remember that you have an image to curate (the whole “ be spontaneous “ doesn’t work with quality men in the early stages of dating. exceptions exist, but again are you willing to bet on a statistical anomaly?). This man doesn’t know you yet, so be prideful and reserved.
  • Always keep a mental distance between your feelings and his flattery or attention. Single heterosexual men, under the appropriate circumstances, will hit on you if they deem you fuckable, fuckable not special. He will shower you with compliments and sometimes gifts (they might be huge for you but not necessarily for him, many men have no issues dropping few thousand to sleep with you, just for the sake of the chase). Wealthy men are still men, they just have more resources to burn on what they want. A man showing you surface-level interest doesn’t automatically mean that he truly likes you. So, getting momentary attention from a man, even if he is of the highest caliber that ever walked on this earth, means nothing of substance. So don’t spend time dwelling on and interpreting it. They are shooting their shots because, first that’s what they live to do, second, they are just working the probabilities. For you to navigate dating successfully, stay in your head and do not let yourself get swayed or swept away, act how you know you should act (do not break character) No last-minute dates, no swinging by your house, no late lousy phone calls …The rules are the rules and you set them so you should be mentally strong and disciplined to stick to them because your rational self knows better than your flattered self.
  • Never start “the talk”, Never ask where is this going, and never express verbally or non-verbally that you like him before he explicitly says it and acts like it. Even if you’re planning your wedding in your head, keep it to yourself and your girlfriends. He is supposed to court you and seduce you into liking him and court you some more for you to approve of him as your potential partner. Never try to pressure him into committing by dropping hints… you think he doesn’t notice, but he does, they all do. Setting standards or being clear about not wanting casual relationships is something you show through your actions and reactions, it’s not something you verbally say without the proper context and timing. And the proper timing is when HE asks for more, otherwise, you just look like you’re trying to bag him. And there is nothing more off-putting to quality men than desperation. And you might think that there is nothing wrong with being direct and you don’t really like playing mind games … You’re totally right. Not all relationships are similar and people are different and complex. Now I want you to decide what kind of relationship dynamic you’re seeking: Do you want to be put on a pedestal, cherished, respected, and valued or do you want the daily hassle of begging your man for a little attention, a man that has taken you for granted. Now that you have made your choice, keep in mind: a man will never hold you in high regard if you throw yourself at him and hand him your love on a silver platter. Make him prove himself to you, you’re the one hiring and he is the candidate. Even more so when he is wealthier than you, more accomplished than you, even if he is the king of some rich dictatorship or a rock star. Never make him feel that he is your big break, that he is the man you’ve been waiting for your whole life. He doesn’t know you enough to form the right impression and take your sincerity as it is, all he sees is a woman who is too eager to commit without taking her time because she saw money (so something must be wrong with her), there is nothing wrong if he thinks he had the first chance because of his money, but it’s wrong if he thinks that’s the only thing that matters to you and it shouldn’t. For all he knows there are a million men out there trying to bag you, so keep him guessing and never say or hint that men are courting you even if it’s the truth and you feel triggered to throw it in his face, you will just come off as an immature teenager. So, keep your reactions under control and do not insinuate that you are the best woman he will ever meet (think it but just don’t say it)
  • In the early stages of courtship, never let him see you when you’re not ready and dolled up. No surprises and swinging by your house while you’re in your pj’s and oiling your hair. Do not budge even if he packages it as a sweet romantic surprise. It’s rarely the case and too early for surprises. If you want to be seen like a lady, look the par.t When you’re not ready to meet him, don’t. A rule of thumb is to never answer last-minute texts that say “ hello beauty, are you home?” right away. Also, it helps build a healthy level of tension in him thinking that you might be on a date with another great man. When you’re from a lower economic class than the man you’re dating, in most cases, he will want to check you out, see where you live, how is your home, and who you are when you’re taken by surprise. Do not allow him to push you out of your comfort zone, and don’t make him feel that he is entitled to your presence whenever he feels like it.
  • When you want to end up in a loving happy healthy relationship with a wealthy man, you have to look beyond the money. The money gets him at the door, it just gives him a fighting chance. Him meeting your financial standards shouldn’t be the only criteria, you need to be conscious of the fact that what makes a relationship work long-term is compatibility, respect, values ..etc. He might be the richest man in Babylon and he is just not for you for reasons that have nothing to do with money. Hypergamous relationships are still human relationships, they might end for a variety of reasons. Do not chase titles and numbers beyond a certain minimum that YOU define, not social media, not family pressure … Stop yourself from being bamboozled by status and wealth, the richest doesn’t always mean the most generous nor most beneficial TO YOU in the long run. Keep yourself in check from time to time and stay connected to your reality and your end goal. Sometimes he is perfect and great on paper, but it’s just not working. Don’t be afraid of the potential loss of what you’ve built up in your head, get rid of the FOMO, and don’t let greed blind you.
  • Now last but not least, develop a strong sense of pride and have the ability to walk away at any stage of the relationship if your expectations are not met. No matter how much you love him, no matter how sad you’re going to be. Learn how to deal with heartbreak in silent dignity, and learn to function when you’re sad, don’t be afraid of being sad, alone, and heartbroken, it will pass like everything else. And learn to live with the harsh reality that he might not chase you back, do not try to give chances that he didn’t ask for, when your rational self knows you shouldn’t, and do not coarse him into loving you and meeting your expectations. Keep yourself grounded and humbled and learn how to digest rejection. Sometimes you can do everything right and he is your dream man but it just doesn’t work, accept it and move on. You don’t need to be loved and appreciated by everyone and you’re never going to, don’t try to force it. It’s very important that you learn how to self-regulate when you’re overwhelmed by emotions, and it’s very important that you know how to identify when you’re weak emotionally and resist the urge to take decisions based on feelings. Do not lower the standards you set for yourself, you have set them for a valid reason before he came into your life, trust your rational self.

So that is it for now, I hope it can be helpful for the beautiful women out there who are on the path to success ( and I hope it wasn’t too long and boring)

I am Celine Gray, a 46 years old woman.

I talk about hypergamy, money, success, and everything I learned from 25+ years of dating up and marrying up.

If this is something that appeals to you, join my email list at the link down below to be notified about my next webinar.

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Celine Gray

Reclaiming femininity & womanhood through power and excellence & glamour.