Sex Q&A: Break the Rules of Dating

Challenge Your Dating Beliefs

Mary from Montreal, Canada asks:

Recently, I’ve gone on many dates with men I meet on Internet dating sites. , I am 54 (people think I am 45), well traveled, sophisticated, a business woman, a former model, who has been married and lived with men before. I like living alone, and have high self-esteem and a decent life. In fact I have had many interesting, accomplished, men from different careers, with great wealth of intellect, accomplishment and money in my life. My problem is this: How can I tell as early as possible if the man is interested in a long-term relationship? I’m not into a casual fling (been there, done that). Right now, at this age, I’m looking for the right fellow. Biology, age and youth aside, are there still some mature men, about 49-60 years old, who would like to date and be with a beautiful, sexy, fun-loving and not a superficial woman of 54? If so, how can I quickly tell without wasting my time?

The reason I’m asking is that I dated a handsome man twice recently, and the chemistry was great. I got hurt, because I had expectations of a potential long-term relationship. He was confused (divorced, not ready for serious dating and not ready emotionally). We ended it. We were on different wavelengths, but the chemistry drew me in, thinking it could be more. Chemistry is not everything; a mental and emotional connection is important, also. Do you have any advice?

Liam’s Response:

Greetings, Mary, thank you for writing. Your perception of the modern American game of amore is not unlike the one held by many independent and successful women; including a rather elitist contractual structure whereby we make lists, take notes, and line up mutual points of education and income. In days of yore, we’d also have insisted that the matches include the appropriate family background, theological disposition and so forth. On the surface, it seems a reasonable and sane way to go about the complicated task of making a match… we nutty apes are forever creating illusions for ourselves about how it all works. You’re not the only one who bought the bill of goods society sells when it came to entitlement and reward based attitudes.

There is a major misunderstanding among women that social attainments and material attributes attract men to relationships. That’s what attracts women. Men work like lunatics all their lives to get the education, the status, the money and the power all for the sake of attracting women. The more competitive and competent a man is in his business and material endeavors, the more opportunities he will have to take lovers and to trade in his current model for a younger, better prospect. Even the corporate executive, who extols his conservative family values, will more often than not have a secret girl (or boy) toy on the side. The men you are trying to land, the ones you insist you deserve by virtue of your own attributes of looks, money and education, are not interested in accomplishments. These sorts are far more apt, by the nature of the beast, to couple long term with women much younger and far less accomplished than you. There are always exceptions, thank heavens, but in general, highly successful men do not want to couple with their equals. For the most part, they will seek young women who can be shown off like ornaments and cater to their need to protect and defend.

That sad fact of life is encumbering enough for women like you. But even more so, is this self-imposed list of social standards you carry around in your head. You seek a man of character, but end up passing many of them by without realizing they are even there, because you’re more interested in what college they attended and what their income bracket is. It’s female nature to seek the best and the brightest but don’t let society determine for you just “what” the best and brightest is. There are lots of men out there who are bright and charismatic and more in alignment with your real relationship needs… They just happen to be the blue collar, working class Joe’s rather than the Donald Trumps of the world. Now, blue collar fellows are no more or less loyal than any other, but the very nature of the working class mandates a more monogamous social philosophy. You’re a woman of refinement and cultured tastes that the typical beer and bowling guy couldn’t interest—but the artisans, the craftsmen… men with no degree, perhaps, but loads of passion… I wouldn’t count these out so quickly, if I were you. Remember, the man who fought for power over passion is the one much less likely to be singular in his affections. His life was spent attaining accolades for the sole purpose of winning female mates aplenty and he deems that his hard-won right. But a fellow of trade, of focus and precision, he might be more the order of the day.

So my advice for you to take or leave, is forget your lists and start meeting people to meet them; to have an experience, not to find a man. Men are generally simple, it’s true, but they are not stupid. The men you’re currently dating see your game and, frankly, and they don’t want to play. Try liking someone for who they are instead. Go live your life for yourself and enjoy the fruits of what you have earned. The rest will come in time.


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7 thoughts on “Sex Q&A: Break the Rules of Dating

  1. Athena

    Liam you are awesome in cutting off the fat and showing how much meat is really there! My advise to women alongside yours is that you desire what you are (Tantric Understanding). My dearly departed father used to say that birds desire birds and fish desire fish. It really wouldn’t make sense for a fish to be with a bird. Would it? Girls, please put those lists in the first garbage can you see, and strike up a conversation with a man you are drawn to without even knowing his name. You will be surprised where it takes you. In this manner, you will see your mirror image in a man. If you are a passionate woman you will desire a passionate man; you will attract each other like magnets. And if you are a woman who desires power and diamonds over passion, then nature will help you align with a man who might smell like money but lacks the Romeo Touch in the bedroom. Nature likes variety and birds of a feather do flock together. If you are a fish don’t expect to be long term with a bird:)

  2. arise

    Once again this author gets so hung up on a woman’s age he doesn’t even answer her question. He clearly has personal issues in this regard. He really should defer to someone else all questions from women “of a certain age” (how patronizing).

    Unless there’s more to this question than was shown, I don’t see the list of criteria he refers to. She looking for a long term relationship with someone mature with whom she has good chemistry. How could one’s criteria get any more basic?

    I recently had an opportunity to observe a very dynamic (and early-40’s – you know, really o-o-o-l-d) internet dater. I’ll share what I learned from her, for the sake of getting some useful information to Mary,

    The most surprising thing I noticed was her challenging approach to potential dates. She started qualifying them in the first email contacts, and over the phone, before she ever met them F2F. Her manner was flirtatious, but more direct than I thought possible. She would say things like, “That sounds kind of beta – I’m really looking for an alpha male”, “Sorry, I don’t date men over 50”, “You should know that I don’t stand for disparaging comments about my body”.

    What surprised me was the men’s reaction. They like being challenged, if it’s done in a teasing sort of way. They actually find getting clear feedback sexy, more so than trying to guess what someone “nice” is really thinking. If you’re fearlessly honest from the beginning, it’s much more painless in the long run.

    For instance, “I’m not looking for a hookup” will be one of the first things you work into the conversation, and if they don’t come right back with a strong statement indicating they’re also thinking long-term, thank them kindly and make it clear you will be looking elsewhere.

    All this requires an attitude of experimentation that doesn’t come naturally to women. You have to be ready to throw them back just as quick as you catch them, easily accepting that the same thing will happen to you. That last part is a bit tough at first, but you only need one person to love you, and as Greg Behrendt has said, “They’re all wrong, until you find the right one.”

    Qualify them by email before you give them your phone number, then by phone a few times before you meet them in person, and again before you agree to a second date. Be ready to release them or be released at every point along the way. Know your limits: in order to, as a woman, release them this easily, you may have to minimize physical contact. Move on to a different dating site, too, if your respondents are a consistent mismatch.

    My dating mentor, by the way, did find love.

    A personal postscript: watch out for stereotypically “handsome” men. They tend to fall into, and out of, relationships easily – why? because they can. Consider ladies, if he’s really got game, he might just be a player. Even if he’s the devoted type, do you really want to be with a guy who gets hit on everywhere he goes? I look for a guy who’s handsome mainly *to me*.

    I’ve also found this book, “The Four Man Plan” by Cindy Lu, a good boundary-setting guide for the modern woman; it’s a quick read that’s funny throughout. Adapt her ideas to your own style. Good luck!

  3. Violet

    Seriously, Liam, Donald Trump only looks good if he’s standing behind a stack of a cash. A very large stack. I’d rather be re-arranging my sock drawer than having to look at that yellow beehive comb-over.

  4. Karen

    I don’t think I read a hint in her letter that she kept lists or were looking for the best man to fit her every need. She even alluded to the fact that the chemistry was the overriding factor in the relationship. Her only requirement is she was looking for long-term. When she says she is not superficial, she probably means it. The quality of maturity men has nothing to do with their accomplishments, but in their ability to communicate in a relationship as to nurish it instead of being a power struggle. Are you sure your reponse was to her letter or to women in general?

  5. diana

    I feel that you did not accurately address her issue. She felt chemistry and fell for someone, and she was interested in a long term relationship with him. But he was just playing the field, as so many men at that age are. Modern men seem to lack the honor necessary to be honest, to say “we are not right for each other” and move on. They stay, and date, lending false hope to the situation.

    I think her question is, how could she be so attracted to someone who was so obviously wrong for her. Once that “chemistry” is released, your list of accomplishments doesn’t mean a thing.

    You are accusing her of going thru your list to determine if he’s the right one, and that’s not what she did. Your response sounds as if you are angry at women who judge men only by “the list”. I think you need to clear your head, and your energy, and re evaluate her letter.

  6. T. Boots

    Liam, of all the articles you have written, I must say I can relate very well to this one. I have been separated (and only recently divorced) for over 8 years. What I have learned in that time is exactly what you advise to Mary. Go out and meet people, men for the sheer joy of the experience, with NO expectations. I met a great man at a New Years’ event. At the time I thought nothing of it. I even attended the party solo knowing I would have a good time. During our conversations that evening he realized that I was a potential client and at the end of the evening offered me his business card, but also extended a personal invite, for a coffee or drink, whatever I felt comfortable with. I did end up calling him for business and while working with him, we started to explore the personal side of the realtionship. We have now been together for over six months as a couple and clearly the success of the realtionship was built on no expectations on either of our parts. On the onset of the friendship, I asked what he was looking for, and if he was even looking for a “relationship”….. we seemed to be on the same page and we have built a realtionship on being clear of our intentions and just letting things evolve. All the best Mary. Just go and enjoy getting to know men for what they are and loving yourself and valuing who you are !


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