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Dating Tips and Relationship Advice from A Failed Matchmaker

Updated on April 3, 2012

Discoveries of a Failed Matchmaker

A while back I received a forward from my brother in law, now usually I don’t write articles about forwards but this one resonated strongly with me for a number of reasons. The forward was about a Slate Article with the catchy title, Sex is Cheap.” (yes it is and Sex also Sells) which is why the author didn’t give it the type of boring academic title I might like, “Shifting Social and Gender Dynamics.” Anyway the main reason the article resonated with me was because it fell in line with a problem I had noticed among many of my single female friends and peers. Many of the ladies I know are single successful women and most of them are having a problem finding Mr. Right. I took a particular interest in this problem because most of my single friends are wonderful women and deserve to be with equally wonderful men. With my fix-it mentality and obsession with matchmaking I set out on a quest to match make my single female friends and their friends and whoever else I got introduced to who was in search of the elusive Mr. Right. Enter Miss Fix-It Matchmaker Mo, cupid wannabe ready to help all her single female friends find a man. Well needless to say after hosting a few single parties, arranging blind dates and enlisting the help of every man I knew I gave up. I realized finding men for a group of single, successful women over the age of thirty was a gargantuan task. Been the curious creature I am, I had to find out why I was failing and why it was so hard for my successful single female friends to find a man. So I came up with a few theories and I made a few discoveries. You can read some of my theories and momentous findings (well not really momentous) in this article as well as some unsolicited advice on finding Mr. Right; what women want and tips on dating a successful woman.

Problem One: Finding a Mr. Right who Matches Unrealistic Expectations

Ladies please be patient with me and don’t shoot the messenger or at least listen for a moment before you fire those shots, and don’t worry in problem two I tackle the men. In this section I outline one of the key reasons women are unable to find Mr. Right. Many of us single women are searching for a man who does not exist and sorry to say is mostly a figment of our imagination.

Unrealistic Expectations Scenario One: The Romance Novel Hero and “More than Man”

Many of us grew up reading (and still do read) romance novels with a handsome, richer, older, more sophisticated, more everything hero and a naïve, young, less wealthy, less educated, less everything heroine. So we expect our Mr. Right to be wealthier than us, more educated, more suave, more successful and in most cases older than us. We were not taught to expect them to be our equals let alone less successful than us. Much as we sing about women’s equality (and believe me I am a proponent of equal opportunity) many of us do not want to be married to a man who is our equal, many of us secretly yearn for the more than man. Now if you are a single successful woman what are the chances you will find a man who is more successful than you. Most of the successful single women I know make six figure salaries, have at least a masters degree (some have doctorates) and are over the age of thirty. So the chances you will find a single man over the age of thirty who makes more money than you do and is more educated are slim. You may find a man who is your equal in the success game but you are unlikely to find one who is doing better than you. While I may be accused of telling successful women to settle for less, I am not, I am simply asking them to be realistic. Really if you are in the top income bracket does your husband need to be and also how many people are in the top income bracket (male or female)? By focusing on how much a man earns and restricting your selection of Mr. Right to six-figure men you have immediately narrowed your pool of eligible men. Much as women do not like to admit it many of us are still waiting for our romance novel hero. Given the strides women have made and the success of many women in today’s world the More Than Man model is outdated and the romance novel hero exists only in books. Once in a while you may be lucky enough to find him in the real world but the chances of that are slim.

Unrealistic Expectations Scenario Two: “The More Than Man” and Measuring Up to Societal Expectations.

This is a continuation of the “more than man,” syndrome but in this case I discuss it in the context of societal pressure. Here I define society as both our immediate inner circle (our friends and family) and wider society in general. Much as we hate to admit it, most of us (both male and female) really care what society thinks of us. We spend our whole lives trying to fit in to society and many of our choices are based on what others will think of us and our preference is that they think highly of us. Society says that as a woman you should date a man who is more than you or at least your equal. So what happens to women who have achieved high levels of success, well the stakes are that much higher for them and the pool of men they should date is much slimmer. Take this scenario, many of the single women I know have at least a masters degree, a few have doctorates, some are lawyers, some corporate executives, others medical doctors and a few are business owners. Now society dictates they should date a man who is more educated or as educated as them, makes more money than them (forget the fact that most of them are in six-figure income brackets), who is in the same age bracket as them (most of them are over 30) and then add on all the other qualities Mr. Right should have and voila it is no surprise that Mr. Right is hard (if not impossible) to find for a successful woman. The unfortunate thing is that many of us are guilty of buying into the societal dictates because when we do step out of the realm of societal expectations we are roundly criticized and punished.

Unrealistic Expectations Scenario Three: The Super-Man, My Father Syndrome

Just as many men expect their wives to be as close as possible to that paragon of virtue known as their mother many women expect their husbands to fit the same mold as their father. Woe unto you if your father was a Super-Man in your eyes. You will walk out into the big bad world and expect your very own Super-Man in the form of your husband. Now if like me you had a successful, intelligent, powerful, wealthy father then the chances you will find a man like him are slim. In addition if you had a father like mine who was the definition of romantic and generous, doted on his wife and daughters, respected women etc.(you get my drift he was the perfect man at least in our eyes) the chances of finding a Super-Man like him get even slimmer. However, if you are lucky enough to have a wise mother like mine she will tell you the man I knew my father to be was not the man she married. He grew into that man partly thanks to been married to a fabulous woman like her. In the early days of their relationship my mother actually made more money than my father and she came from a wealthier background than him. Now if she had used all of the silly standards that we use for finding Mr. Right then she never would have landed with the fabulous husband that she did.

I am sure you can come up with more categories of unrealistic men but based on those three alone it is no wonder that a good man is hard to find or that there is a so called “scarcity of good men.” If a good man aka Mr. Right has to meet all of those high, sometimes unrealistic standards then the “good men” out there who also happen to be single and over the age of thirty are rare.

How to Find the “Real” Mr. Right and Let Go of the Fictional One

Ladies examine your expectations and be brutally honest with yourselves. Are your expectations realistic? In cases where they are not consider adjusting them so they are closer to reality. Also look at the substance of the man, is he a good honest man, does he treat you well, is he loving etc. versus external factors like high-paying jobs. At the end of the day a teacher who treats you and your children well may make a better husband than a high-powered executive who has no time for you. (NB: This is just an example there are loving and caring executives out there). Also examine what you really need out of a relationship then look for a man who can deliver that. Only you know the type of man who is right for you do not mold your Mr. Right based on societal expectations and fictional romance novel heroes. Take the example of a lady who is in a high-paying job and constantly traveling, does she really need a wealthy husband who is also super-busy and makes as much or more money than she does? Maybe what she needs is a husband who works in a job that gives him time for his family and the type of man who is supportive and not threatened by her success. So in that case she can strike “rich and high-paying job,” off her list of qualities Mr. Right must have and she will find her field of available men suddenly widens. So take a moment to assess and re-write the list of qualities your Mr. Right must have, be flexible about factors like age, race, income level, education level, job type, geographic location etc and it will be much easier for you to find Mr. Right. Qualities like honesty, responsibility, kindness and chivalry are universal and not specific to certain types of men. So change your thinking of what constitutes Mr. Right and all of a sudden you will realize that a good man is not hard to find. What is hard to find is a fictional Mr. Right.

Problem Two: The End of the Successful Man and the Dawn of Mice

In problem one I was a little hard on the ladies and I gave some of the reasons why I think they are having difficulties finding Mr. Right, now as promised I examine some of the issues many single women are complaining about when it comes dating and men.

1. The Less Ambitious Man

In problem one I addressed the issue of high expectations among women, while some of the ladies’ expectations may be unrealistic (such as expecting men to have Donald Trump’s money, Brad Pitt’s looks and Mother Theresa’s heart) some of their expectations are well in order. A common complaint among women nowadays is frustration with what appears to be much lower ambitions among their male peers (for a more in-depth look at this read the Sex is Cheap article,” and The End of Men ). I did not have to refer to the articles to figure this out because all around me are examples of my female peers doing much better in terms of careers and education than their male peers. I think this diminishing ambition among men can be partially explained by the following factors:

(i) The modern day male is no longer the sole breadwinner in the household and he is aware of this. He knows the responsibility of providing for his family no longer falls solely on his shoulders so he is no longer as driven to find a high-paying job that will maintain him and his family in a comfortable lifestyle. He can be content knowing that most likely he will be part of a two-income household and in some cases his wife may even earn more than him.

(iii) Lowered Societal Expectations: This point falls in line with point number one. Society no longer puts a lot of pressure on young men to get an education and get a good job so that they can provide for their families because as pointed out above men are no longer the sole breadwinners.

(iii) The “Girl Child,” Movement: I see a hail of bullets coming my way so let me start by stating for the record that I am not against female empowerment and I agree that in many cases there is a need to level the playing field. However, while there has been a lot of encouragement for girls to achieve there has been little if any attention paid to the male child. Thus, while girls are been taught to be "all that you can be," and the sky is the limit the boys are been left to their own devices. One of the effects of this has been the emergence of strong successful women who are “all that they can be,” and weak men who in many cases are simply not as driven. Perhaps, one of the lessons we can take out of this is that all children (both male and female) need encouragement to succeed.

2. The Insecure Man and the Shrinking Successful Woman

Another common complaint among single successful women and part of the reason they are hesitant to date less successful men is the fact that both society and men appear to feel threatened by them. There is a constant assault on the single successful woman and an attempt to get her to be less than what she is in order to “get a man.” I do not think anyone should be less than what they are to get a mate. I was actually once told by a pastor that my younger sister had better get married before she gets her Ph.D. or she will never find a man and that when she gets her Ph.D. she should keep it hidden. I have another sister who is a medical doctor and just for the fun of it I put on her white coat while we were on the street. She quickly told me to remove it because I would get one of two reactions, “men won’t want to talk to me because they will assume I am a stuck-up doctor,” or I will get hit on by all sorts of shady characters who think I am a meal ticket. I know many successful women who do not fit the negative stereotypes of a successful woman. They are warm, down to earth loving individuals who relate to men in much the same way that less successful women do. However, they are often punished for their success.

3. The End of Men and the Dawn of Mice

This leads me to the final problem many single women are complaining about. I like to call this the end of men and the dawn of mice. All of a sudden we seem to be dealing with a society of men who are scared to approach women, while men will deny this strongly it is happening. Even my older female relatives who often pity their successful daughters are admitting that it is tough out there and men are no longer what they used to be. Back in their days men would approach women, charm them and court them which is very different from the scenario now. Men also had a sense of pride and responsibility when it came to providing for their families even in cases where their wives worked (nearly all the older females I know worked and were independent women). Now what we are seeing is a pack of men who women can place in their pockets as one of my aunts who is in her seventies says. While the successful woman suffers most in this scenario (because she is the most threatening of women) even less successful women are complaining. However, since this article is dealing with the single successful woman I will focus on her and the approach the mice in the dating game use to deal with her.

(i) One of the ways mice deal with the successful threatening woman is by not asking her out. Now before all of you start putting this down to her looks some of the successful women I am talking about are actually very attractive women by any standards. When they walk by men swivel their heads but never approach them. Other than the brave usually sleazy men who are so used to been turned down that they will try asking any woman out. So no, it is not about the ladies been unattractive. Unapproachable perhaps but certainly not unattractive.

(ii) The second way mice deal with the successful woman is by constantly talking negatively about her especially in social gatherings trying to cut her down to size in the hopes that she will then be on their mouse level. After going through this enough times the single successful woman then gets scared of mice and decides she better stick to real men who she assumes are all built in the mold of the “more than man.” They wrongly conclude that if a man is successful he will be less intimidated by a successful woman. However, this is not always the case I have come across successful men who still behave like mice which brings me to point number three.

(iii) The Ideal of the Less than Woman: Men have their own expectations and some of them even read the same romance novels that we did. Consequently they want to date and marry women who make them feel like more of a man. They prefer a woman who is less educated, less successful career wise and one who makes less money than them. During my brief period as a failed matchmaker there was a guy with a Ph.D. who was seriously looking for a wife, he did not want a woman from the city and preferred a high school graduate. He was willing to date an educated woman so long as she would not keep shoving it in his face (his words not mine). Needless to say in my opinion this successful man falls into the mouse category. This man may be the extreme but in general what you find is that men prefer to marry a less than woman or at best an equal but rarely if ever a more than woman. Society is also partly to blame since men are expected to do better than their wives. So for example people will frown on a man who is married to a high powered female executive yet he is a clerk or a blue collar worker.

Dating Tips: What Successful Women Want in a Man

Here is what I have gathered from my conversations with single successful women, if you want to date a successful woman then these are some of the things you need to do:

(i) Be Bold, Go Beyond the Stereotypes and Ask her out: I think it should start with the shattering of stereotypes about “successful women.” Gentlemen, the next time you meet a successful woman take time to know her and don’t judge her or write her off because of her stellar qualifications. Like I said some of the most feminine, down to earth women I know are successful women. Contrary to popular opinion some of them do enjoy cooking (when they get the time) and pampering their men. So go beyond her titles and get to know the real her before forming ideas of what she is like. You just may be missing out on a gem because you are caught up in stereotypes.

(ii) Be Secure, Confident and Have Healthy Self-Esteem: I can tell you this firsthand the one thing successful single women fear and dislike is insecure men and men who are scared of them. So be bold, be confident in yourself and have a healthy sense of self-esteem. Some of them even appreciate a little bit of cockiness, not to be confused with been a jerk.

(iii) Have a Job and Be Financially Independent: Given the current economic crisis in many countries and the layoffs and job losses that have occurred as a consequence of this, some women may be a little more understanding on this particular point. But in general women prefer that you have your own career and be capable of supporting yourself financially. You do not need to make as much money as she does, but most successful women expect a man to at least have a job and be capable of paying his own bills.

(iv) Be a man and do the manly things: When you start dating, treat her well and do the manly things around the house. Just because she’s a powerhouse at the office it does not mean she wants to run the show at home or do stuff like changing the bulbs and oil in the car. I remember one of the single successful women I know saying to me and another friend, “I am tired of changing the light bulbs.” By the way been a man also means we expect you to pay on dates at least in the beginning after that once in a while we may foot the bill but we still expect you to pay for the dates most of the time.

Breaking Out of Our Expectations and Comfort Zones

As you have seen a lot of this article is based on expectations, stereotypes and comfort zones. We need to stop confusing our intimate relationships and marriage with superficial qualities. I think if we start there and go back to our roots we will find what we need and ultimately what we want. So re-write your Mr. Right and Mrs. Right lists focusing on what you need not on the superficial qualities society tells you, you should look for. If what you are looking for is love and companionship then you will find that special someone can come clothed in any form. They do not come in a one size fits all package and they do not come in cardboard brown labeled boxes. Learn to look beyond the labels and boxes and you will be surprised to find that you have found your Mr. Right or Mrs. Right in the most unlikely places.

Wikimedia Drawn Love Hearts
Wikimedia Drawn Love Hearts | Source


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