2185. Dating in Mid-life — Part D9: Closing Notes and Tips

It isn’t news. Dating in mid-life is a female-designed development to capture a man for life. The older the man, the easier the capture. This series closes with a few miscellaneous tips that previously didn’t make the cut. They’re my final contribution to give women an advantage.

  1. As you know, modern social values, standards, and expectations are designed to produce sex at the earliest and without obligation even of gentlemanly politeness after conquest. Chastity doesn’t sell; your virtues sell and overpower the delay of bedtime. If you can’t make yourself unique, you’re like all the other gals who can easily capture but can’t keep a man.
  2. Unless he’s been operating in the dating market for some time, he’s as amateurish as you. You can take advantage of that with your knowledge of relationship dynamics.
  3. The more elaborate and expensive the date scene, the advantage turns to him; he expects and deserves more and you’re more obligated. The simpler and cheaper the date, the more advantage turns to you. Don’t think money and time on this issue. Think complexity of personalities merging into common thought, getting together because of mutual likeability, enjoying company together regardless of where and when. For example, try coffee at Mickey D’s several or many times before a first real date. Grow the relationship before you let the emotions emerge into sight. The sooner he spots your deeper interest, the sooner he disregards you for sex with you. Also, unless he earns your attention and learns how to keep it, he won’t appreciate you very much. And your attention is YOU eyeball to eyeball with your ears wide open and empathetic to his story. Not in a romantic setting where you’re thinking romance and he’s expecting a listener for his sales effort. Learn to delay romance for awhile.
  4. It’s a one-way street. He initiates and you put up speed bumps. If you’re so fearful of losing him that you accede to his wishes, you will lose him. Men don’t respect pushovers, people they can dominate at will, or women who don’t put up a struggle to protect their greatest asset.
  5. His success is getting his way. Your success is slowing, slowing, slowing his advances until you get your way. If you can get him to court you for a year or two without conquest, you will probably receive a proposal. Maybe sooner. It’s also a more permanent relationship that you generate.
  6. The immaturity of so many men, aka adultolescents, makes the dating scene more unpredictable than you expect. Let teen-like incidents of behavior make you see red flags. Or, if you could live with what he’s like, then a pink flag. Disrespect and demeaning of women generally should be a bright red flag, even though he may try to persuade that you’re an exception.
  7. Your being more mature, men aren’t so difficult to figure out. Most importantly, you have to know and decide what you won’t tolerate. That is, decide just who and what you are and be proud of it.
  8. Older men should be more predictable than younger men, but don’t count on it. You have to test but don’t challenge any of them in ways that question their self-respect, masculinity, capability, trustworthiness, or dependability. In short, their character. They still guard their masculine nature.
  9. Men continue to look for the proverbial ‘good woman’ to mate with. But they perceive far less valuable women. Women don’t play up their uniqueness other than for sex. Men use personal experience and popular opinion to judge women in unattractive attire or being promiscuous and find them wanting for permanent mating. They don’t qualify as ‘good’ in man-think.
  10. Rather than await a woman’s discretion about yielding sex, modern men have learned to barter aggressively. He’s tough to beat at the negotiating table. But you should draw the line. Send him packing as the player he is when he tries to use shame, guilt, or claim you’re being old fashioned. Players start from the foundation that you’re not respected and therefore disposable whether you cave or not.
  11. Momma’s boys and ‘never-marrieds’. Both are already devoted to momma and self, so the likelihood they can become devoted to you is slim but not dead. It will probably take at least a 2-year courtship to win their devotion over whatever exists in their hearts when you meet.
  12. Do his actions match his words? If not, it’s a huge red flag. Take time to observe closely about many and little things.
  13. Does he frequently hurt your feelings? Seemingly without remorse? If so, beware. Escape now.
  14. Measure each man’s love by his devotion to you and measure by his acts that please rather than impress you. For example, how easy does he display affection and appear to thoroughly enjoy himself for doing so? If showing you affection is a burden to him when not after sex, beware. How do you tell the difference? Look to your heart, assess his actions, and trust yourself that you know what you’re doing or about to do.

Closing. This series grew humongously. Expecting five or six articles, it grew to over two dozen. These are important reminders that may or may not have been mentioned, but which I want to leave with you.

  • Fear not, you can do whatever you choose. God prepared you well if you follow your heart. Look for men who follow their heart, their male nature, their masculine dominance without guilt, their regard and hopefully respect for others, and their specific respect for you.
  • If a man doesn’t like himself, he can’t reflect an affirming attitude. He can only like you as much as he likes himself (which is the subject of an upcoming, revealing, and important article).
  • A potential candidate for mating should find you. You get to judge whether he’s as good as he claims and whether that is good enough for you. He’s the seller, you’re the buyer. Don’t change it because you would or do like a hunk, dream boy, or father figure.
  • Being a trophy has a way of backfiring a decade or two down the marital road. Men tend to go into role reversal with a great age difference.
  • Teen-like behavior in men may go away over time if they respect and accept your leadership examples of mature living.
  • Submission is his term. As he views it, however, it’s unrealistic for you. Submissive is your term for overriding his concept and making your marriage manageable.
  • He walks himself to the altar, if you don’t turn him off out of ignorance, impatience, or ingratitude.
  • Mutual attraction begins with similar interests, but it’s sex differences that provide the glue of longevity. (Too much alike leads to boredom.)
  • Each man’s urge to conquer you is the elephant in the room. Virtual virginity is the big gun for shooting the elephant between the eyes and enabling him to fall into the friendly bush of domestic life.

Ladies, I hope your dating days are smoothly exciting and profitable for your wishful inputs. Good luck and may God both endorse and reward your sincere efforts. I hope this series earns a little credit for helping.


Filed under courtship, Dear daughter, How she wins

15 responses to “2185. Dating in Mid-life — Part D9: Closing Notes and Tips

  1. Magnolia

    Amazing series.

  2. Eb

    Thank you for this series Mr. Guy. With regards to #4. The one way street concept is so true. These days I hear from a lot of guys that they don’t know who should initiate or if they, as the man, should always initiate.

    Your Highness Eb,
    Next time remind them of this. Initiators are leaders. Leaders determine outcomes. Outcomes determine winners and losers. Smile throughout and don’t explain further or complain about others.

    • JuJu

      I do feel a little bad about that point because the (older) guy I am interested in did not initiate our first contact (online). I was able to see on my profile that he had been looking at my profile fairly frequently for months, and on one of those days he had looked (and after my messy breakup) I messaged him and asked if he was going to make me say hi first. He wrote back with lots to say and commented that he didn’t think I would be interested because of the age gap and we have taken it very slow from there. He has told me that all his life he’s had trouble initiating with women and I hope i’m in a better role now as the ball is in his court as to contact and he goes above and beyond trying to keep me interested while I stand back a bit coolly (but kind of obsessed underneath it all). However there is that nagging fact in my mind that I did contact him first and wishing he’d taken that chance on me albeit at the time I messaged him he was almost a year into talking to someone else (which he told me up front and it later did not work out). He was the first guy I ever wrote first…

      • Cinnamon


        Don’t worry about having contacted him first. Don’t mention it to him again and don’t let it nag you. Older men can lack confidence based on an age gap – his story is very plausible to me. If he mentions it smile sweetly, look up at the ceiling very innocently and say something like “hmmmm… I’m don’t know what could have gotten into me that day….but I’m glad it did!” Then shut up and keep smiling. Wait for him to change the subject. If he doesn’t, keep smiling but don’t reveal any more details about it. Deflect with silence and charm. Presto! Problem solved.

        Just go into “recovery” mode from now on. Let him lead, smile sweetly when you follow using the principles of WWNH. As Sir Guy says, if he wants you he will let you know without interference from you.

  3. surfercajun

    @ Gentleman Eric
    ~ Isn’t a report that was asked of you due soon? 😉 I am eagerly waiting…..

    • Eric

      Miss Surfercajun:
      LOL—yes, I’m working on it. I was also reading the current series of articles, so it should be up next week!

      • surfercajun

        My little bubble thingy lit up! Nice to see you here once more! Thank you for taking the time to respond to me. You are always such a gracious gentleman. 🙂 Now I am excited to read it!!!

      • surfercajun

        Gentleman Eric,

        8 days go by and no report? (clicks teeth) Now I am shocked…. 🙂 Yes, you wrote (should be) I read (will be) …giggle

  4. Miss Kitty

    hmm NO 8
    is very true, since this is 2015, and some older men in their thirties are very immature… blame SEX, DRUGS, and ROCK culture
    unless he is ‘raised right’ but even then you cant take any chances

    • Cinnamon

      Actually it’s even worse than that. Some men in their SIXTIES and SEVENTIES are very immature!

  5. prettybeans

    Sir Guy,
    I do hope that your post-birthday year is coming along swimmingly.
    Completely unrelated to the topic at hand, what do you make of ladies lending money to men?
    (Especially in the case of a lady lending to a man who is not a close family member)
    Thank you.

    Your Highness Prettybeans,

    Thank you, sweetie pie, for the birthday wish.

    As to loaning money, I discourage it. For women it’s high exposure and too much disclosure. Too easy to misread or take too far your intentions. If a boyfriend or hope-to-be boyfriend, you’ll likely lose him before he pays back a large amount. Men and their character are too easily parted on the back of a tender-hearted female.


    • prettybeans

      You make me smile Sir and I am especially grateful for your seemingly happy mood today 😉

      I have enjoyed this series particularly the reminders and tips to look out for.

      I’m also looking forward to the article that you have promised to expand on point #2 in the closing section – about men who dislike themselves and by extension cause hurt others. I would like to be able to spot the rubbish from a far off and steer clear!
      Most grateful Sir!

  6. gonemaverick

    Amen to the last paragraph!

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