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Does initiating EVER work?

March 17, 2017

Let me tell you why some people claim it works when women initiate. Both women and men have told me this. Even some of you readers!

Now don’t think I ignored you. I pondered for a long time on it. But I think I’ve cracked the mystery…

One man I met last year told me, “If it weren’t for my wife telling me she wanted to date me, I would never have gotten around to it.”

Now this man and woman are pretty happy together as far as I know. And they’d been married for a long time.

So why follow my advice that as a woman, you shouldn’t initiate? Since I can’t assume you are convinced just because I say so, I will lay it all out for you. I will tell you why initiating works for some women with some men. Then you can decide if you want to do the same.

When would initiating work?

Besides approaching a man in the manner and under the circumstances delineated in my EGuide “How to Show Your Interest in a Man”, which should be in every Prize Catch’s dating arsenal, here are the instances where your initiation is more likely to work than otherwise:

  • When you are initiating with a man BELOW YOUR LEAGUE (as in level of attractiveness, education level, income level, position in society, etc.) Example: You are a nine in the looks department and he is a three. You have a college degree and he is a high school dropout. You come from parents who are doctors and he lives in the trailer park. You are 25 and he is 55.
  • When you are initiating with a man who may or may not be in your league, but has self-esteem issues, lacks social skills, or has some kind of limiting belief that temporarily keeps him passive — all of which he is WILLING TO OVERCOME because of you. The man I mentioned above had doubts about being in a relationship again after a bad divorce, and after the woman initiated enough times, he found himself enjoying her company so much he decided to commit to her and eventually marry her. She was also 20 years younger than he was, so she had two factors in her favor when she initiated. It was a gamble of course for her, because she could have wasted her time on him if he hadn’t responded to her positively — which can happen even if a man is below your league.

You get the gist.

This is why rich, famous women can initiate and have relationships work in their favor. Most of the men they encounter and are attracted to, while perhaps younger, are below their league in terms of income and position in society.

And this is also why men face more challenges when they initiate with women above their league than when they do so with women in the same league or below their league.

This “league” is a popular term that is thrown around a lot but it does accurately describe why most couples are usually of the same league (as in level of attractiveness, education, income, and background). And why there are fewer couples out there with a big disparity between them, where one is obviously out of the other’s league in every category.

Of course, what constitutes a “league” can be pretty subjective. If a man you are in love with is overweight and you’re not, but you don’t mind because he’s a gentleman and knows how to make you happy, you wouldn’t say he was below your league even if your friends think so.

So, voila. now you know when initiation MIGHT work.

And let me add, because most women almost instinctively want to end up with a man in the same league or higher, avoiding men “below their league” if they can, it is imperative that these women do not initiate with the men they are attracted to. Chances are, it just wouldn’t work.

Now if these men were below their league, these “higher-aiming” women would have a better shot.

Of course, there are exceptions to everything, as a man “below your league” can still lose interest or won’t commit. But hopefully this gives you a clearer picture as far as when initiating can work and when it most likely won’t. So if you are one of these “high aimers”, you’ve been duly warned.

Get the secret weapon in dating and relationships when you Order EGuides Today, or Get Personalized Advice via confidential Email Exchange.


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  1. J. L. permalink

    Hi OneTruth! I am in a new dating situation and pretty confused about what to do. I just ordered the personalized email exchange. Hope to hear from you soon!

    • Jane,

      Thank you for purchasing the email exchange and glad you got the resolution you needed. It was a pleasure helping you. If you need anything else in the future, please let me know.

  2. Meera permalink

    I agree with you that asking out guys never works but I’ve only been asked out by guys WAY below my league. Guys in my league do not ask me out and the ones above ignore me completely. How do you explain that?

    I know league is subjective but apart from physical and personality attractiveness, the other factors of league are fairly objective like income, education, success etc. So how come guys below my league keep hitting on me and they’re the ONLY ones who hit on me?

    I have two Bacherlor’s degrees and a master’s from Harvard, spanning several fields-chemistry, psychology, neuroscience, health and communication. I work in development, earning reasonably well but not rich, come from an upper middle-class family (my dad is a doctor, my mom is a biochemist, brother is an engineer, also an Ivy league grad).

    I’m also a professional dancer, I sing, paint/sketch, play music, am an avid photographer, speak 4 languages (international), widely travelled, a huge lover of literature (have read almost all the classics and love poetry), theatre, movies and most forms of art, interior decoration. I’m a major foodie and can cook several cuisines fairly well, love to do semi-adventurous things (e.g. paragliding, hiking, road trips but not rock climbing or very dangerous sports).

    Looks-wise, I’m ordinary but kind of cute, I’m short (5′), medium build, long dark hair, clear skin, not very fashionable but more on the modest side.

    Personality-wise, I’m an introvert and romantically shy but also playful when I’m comfortable, straightforward, I’m serious but also love to laugh and have fun, extremely loyal and conscientious in relationships, well behaved and I have my share of faults as well. I have never been married.

    The guys who ask me out are wayyyy often are not as educated as I am, are unattractive in some major way i.e. overweight, weird looking, not very successful or well off. They insult me, mansplain things to me and are annoying. I have no choice but to ignore them. They do not impress me.

    I just want a reasonably cute guy with similar levels of education (Ivy league degree or equivalent), money, success, family background as I have who shares my values, sense of humour and some of my interests. Race, religion etc. doesn’t matter. I cannot find guys like these. The few I have met did not ask me out. Is this too much to ask for? Is wanting someone in my league unreasonable? Am I so physically unattractive that no guy in my league would ever ask me out even if I have other traits?

    Most regular guys with Master’s degrees and decent job/looks also do not ask me out. Basically, nobody really asks me out, except flirts and sometimes married men hit on me.

    Smart, successful, rich, sophisticated or good looking guys simply ignore me. That’s fine because I don’t want guys above my league because they’ll probably cheat on me but I want someone within my league. I see plenty of other women like me, even worse than me, getting hitched.

    I’ve been following all the rules by The One but remain single.

    • Meera,

      I understand your plight. There are men who have very little going for them, so most women they find attractive are out of their league. You would be one of these women they find attractive.

      Why don’t men in your league pursue you? Well, first off, please be aware that there aren’t that many of them. You’re accomplished professionally in different fields, you’re talented in different skills, you’re multilingual, you’re well-educated, you’re sophisticated, and you come from an upper class background. If you were a man, you’d have a hard time finding a woman in your own league!

      The entire world is made up of mostly people living mediocre, ordinary lives. They are not high achievers nor do they possess multiple interests, accomplishments, and notable talents. Whether it’s due to lack of opportunity or lack of drive, most people are either trying to survive or working in mundane jobs to live and support a family. They might take a vacation or do something fun on the weekends, but they make up the majority of the human population everywhere. They have lots in common with one another. The single ones easily meet one another and match up. Even the divorced ones are able to get new partners, due to the availability of similar people — people in this league.

      So this is one factor that contributes to the difficulty you’re facing, given that you want someone similar to yourself, when you are anything but mediocre and ordinary.

      Second, it’s possible you’re not meeting enough men you find attractive who are in your league. If you’re interested in meeting these men, you would need to go where they go. It could be through working in a specialized field, class reunions, Ivy League online dating sites, etc. However, as in life, there are no guarantees. You could end up meeting nobody in those places, and end up meeting one on the bus.

      Basically, you need to be out in the right field for men to scan, as it could very well be you are not in the right places. A woman might be considered attractive in one area of the country and less attractive in another area of the country. A city slicker may find herself undesirable if she lives in cowboy country. Not saying you need to move, but sometimes location matters, and you will have to change up your routine and where you socialize.

      I think it’s a good idea for any single woman having a hard time meeting men to simply set time aside to increase her chances. It’s like having a pet project. It’s not a full-time gig, but you do spend time on it. What this will involve is putting herself in venues where she doesn’t usually go to. It could be a social event, volunteer work, a class, a conference, or anything that she has an interest in where there are men with similar interests.

      In making this happen, you’re increasing your chances and not waiting for him to appear at your doorstep. Not only that, you will enrich yourself in the process anyway. It would be fun! The EGuide “Be a Prize Catch Single” talks about the importance of creating your own happiness during the journey of life, rather than focusing on a guy as the destination.

      This is, of course, if you’re not too put off by the idea.

      Lastly, there are plenty of couples who have league disparity but who are in long-term, successful relationship. I understand you want what you want, but you will either have to accept that being pursued by a guy in your league may not happen, or you have to try to be open about dating someone different from what you thought for sure you wanted. Perhaps a guy may not be Ivy League material, but is accomplished in equally impressive ways and possesses admirable qualities. What if there’s a spark with a guy like that? What if he pursued you?

      I just wouldn’t want you to feel doomed that nobody you find attractive is asking you out. That’s why I made suggestions of proactivity. Plus, sometimes we need to explore the unknown. What if you’re not supposed to stick to what’s comfortable and familiar? What if the obstacles you’re facing now is challenging you to grow and expand as a person?

      • Meera permalink

        Thanks for your wonderful reply The One. I didn’t mean to come off as snooty and that I was out of most people’s league. I did meet a lot of similar guys during college and universities. The kinds of place I went, there were plenty of smart, talented people but at that time they were very young and immature and hence I had trouble connecting with them. None of those relationships would have worked out anyway because we all moved in different directions for our careers and lifestyle choices. I would not have developed into who I am if I had married young.

        I would be delighted to be pursued by a guy who wasn’t Ivy League material but was accomplished and interesting in other ways and had good character. The problem is, I don’t meet those kinds of guys. You have to be driven to stand out in some way or be successful and so these kinds of guys are workaholics who have no time for relationships or very arrogant because they are successful and swamped with female attention. They also seem to want hotties. I am not the model type, more the studious, serious type. This combination doesn’t work.

        What I have also noticed is that guys who haven’t accomplished as much spend an inordinate amount of time making me feel I am not all that great. They point out my mistakes, find imaginary or trivial faults with me just to prove that they’re better than I am. If someone isn’t all that accomplished, I honestly don’t care but they need to be secure and confident in themselves. That’s why I stick to my so called league because these guys can better handle me–there is nothing to prove–we are already similar. It is hard to find a guy who is doing well in life and is at peace with himself, regardless of his achievements. I want someone who can admire me too without feeling small himself. I have no trouble admiring others. I don’t feel jealous or small. Why is this so difficult?

        Whenever I have tried to make less confident guys feel more confident, they end up walking all over me. I can’t take that anymore so I’ve stopped. Very few couples can manage with league disparities.

        I have dated among Ivy league groups or groups that share my various interests but without success so far. Perhaps they also want someone unbelievably amazing and I am not that. I know a lot of very accomplished, smart, handsome, talented men who just want a beautiful woman who waits for them at home. They are NOT looking for an equal partner.

        I remain totally open to dating outside my league if the guy is attractive enough in other ways. I just keep getting all round losers-like actually mean, delusional guys that you would not recommend.You’re about investing more time and possibly moving to another place. I am trying for both. So we shall see.

        • Marie permalink

          Hi, Meera. I’ve been following the thread– it’s been very informative and quite revealing. I too appreciate the thorough response from The One; it was somehow all-encompassing. I justice wanted to add that according to your self-description, you’re amazing and any man would be fortunate to share a life with you. Stay confident, positive and moving forward– don’t allow anyone to make you feel any less than who God made you to be and who you have become in your journey through commitment, dedication, perseverance, selflessness, and continuous personal growth. Best wishes!

        • Meera,

          You’re very welcome. You didn’t come off as being snooty at all, just self-aware and realistic!

          Guys who have to diminish you in order to feel better about themselves are definitely ones to stay away from. It’s good you’re recognizing that.

          Keep in mind that there are both insecure and confident men who do that, just as there are insecure and confident ones who don’t. The first sign of critical behavior is the red flag that tells you to move on, regardless of his accomplishments or lack thereof.

          While many successful, attractive men just want a trophy wife, there are also men who are looking for a woman like you and would appreciate your unique qualities (who also wouldn’t put you down because they feel threatened).

          Glad you are open to the idea of shifting locales and expanding your opportunities in meeting new men. Think of it as going on a journey of discovery with unexpected rewards. The right man may show up, or he may not. But sitting at home wondering where he is certainly won’t be as interesting!

  3. Sarah permalink

    this is so true…and also so frustrating because i never meet guys in my “league”….they’re all so immature, or i can see right through them, or they’re emotionally unfit and i feel like it’s impossible to find the kind of man that could pursue me and keep up with me….this has led me to feel really down and discouraged.

    but what the one is saying is the truth, ladies take heed. i’d rather be single with my dignity than in a relationship and gasping for air.

  4. Marie permalink

    Your “instances” while amusing, are not just sensible, but true-to-life! Like many inexperienced, eager to have a family young women, I married at 20…. Fast forward 30 years and I am single, with five grown adult children, one grandchild and not currently dating. While I may be single out of choice today, I have learned invaluable lessons from you and a few select others that have made a significant change in how I think, view myself and men. If I should come to a place in the future, where I am faced with the decision to marry, it will be my forever-after…with my prince and the one who deserves me. He who will cherish and revere me, receiving equitable respect, loyalty and love from me. Not because I am above all others, but because we are likeminded, kindred spirits, and walk on level ground. Thank you for imparting insight as you do! To know at any age that you don’t NEED to settle, is the kind of liberating empowerment that offers genuine hope for a quality relationship.

    • Marie,

      I’m pleased you have gained something from this blog and you are empowered and liberated. No, you don’t need to settle when you know how to make yourself happy and are willing to receive what you deserve. All the best to you!

  5. Belinda permalink

    I don’t think it initiating ever works. Even with men who are below your league. In fact, I’ve seen it totally backfire on girls who have had this thinking. They eneded up getting dumped by losers and unattractive guys. Men have tp really want you for some reason….otherwise they will definitely use you or take advantage of you. Sure if you are a rich woman, they will marry you to mooch of you for life…..even losers! Don’t be pathetic ladies. Don’t pursue.

    • Belinda,

      Yes, initiating is best when men are doing it!

    • I would have to agree with you after my recent divorce. I was the initiator. He was below my league. I have an advanced degree. I am tall, attractive and modeled for department stores. He ended up using me financially and did not want to work after a certain point. I felt alone and emotionally abused (he started cursing me and ignoring me). I was loyal, kind and caring but ended up losing big time. It is always better when men pursue because at least you know they really want you for you.

  6. Whoah! Another revelation from One truth.
    I’m utterly gobsmacked at the accuracy of your theory.

    I’d also just like to add that on the flip side you can’t initiate with guys in or above your league because they are Not passive, they don’t care what you or anyone thinks and they do what they like, not what they’re told.

    They’re also confident and wired for the chase which is what attracts them to you, if you lay it out like a buffet, they’ll run out chasing the wild gazelle. They always chase a challenge, they don’t settle for self surrendered carrion (frankly).
    If you try to convince them of you, they will run like hell. They don’t want to be told or ‘Sold’ on anything and all you’ll do is lower your value, and appear as a cheesy agenda driven salesman which no one likes.
    They want to discover you for themselves and if you’re truly feminine and high value, you’re alluring and only want those who will chase and discover you all on their own.
    High league is high stakes. Survival of the emotionally fittest is key.

    Wishing you all the love you need and much appreciation to The One for another Gem!

  7. Spot on

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