Matchmakers on the Challenges Men Have in the Dating Scene Today

The dating scene has become a very confusing arena for men. I have heard many women complain that men today don’t take initiative to pursue them romantically in real life, but rather hide behind the various online dating tools to initiate contact. In return men claim that by approaching a woman the old fashion way they risk being considered rude, offensive, or even being accused of sexual harassment, it all depends on the perspective of the woman or her mood.

We live in a society in which gender roles are not as clear as they once were: men are not the sole bread earners anymore and more women enjoy economic independence, which gives them more social and personal freedom than ever before. This reality has a direct correlation to the perplexity in the current dating scene. While many men accept that women are equal to them at work and in society and treat them accordingly - when it comes to dating, people still hold on to traditional gender roles: many women still expect men to make the first move and engage in the romantic pursuit of them, some men still want to demonstrate chivalrous behavior with women. Nevertheless, since there are no longer clear rules of expected courtship behavior, men are left to guess what would be acceptable or desirable with each woman they approach. It can be tricky business for men.

I have asked matchmakers from around the world, including the USA, Canada, UK, Australia, Spain, Israel, and South Africa, to reflect on the dilemmas men encounter today when dating, to voice the challenges their male clients shared with them, and to share their advice in the matter. By initiating this project I would like to achieve two goals:
1.     To raise awareness about the confusion men experience today when trying to woo a woman.
2.     To stir up a social discussion about how the changes in gender roles have been affecting courtship, dating, and the relationship between men and women.

If you have any thoughts or comments on this topic please share them here.

I would like to thank Belinda Leung from Muse&Co. for her consolation on the subject.

Susan Alper - Susan Alper Connections Inc., Montreal, Canada


They used to say it was hard to be a woman in a man’s world. Today I think it has taken a complete 180 degrees turn - it’s hard to be a single man in the dating world.

Back in the 1950s, 1960s, or even the 1970s the dating scene was simple: women looked for a man who would be a wonderful father and husband and a good provider. Men looked for an attractive woman who will take care of the house and raise the children. Since the eighties woman have come a long way in becoming men in woman bodies; they are independent, busy, and not so needy. It’s become extremely difficult for men to truly understand what woman want.

Men today have to try twice as hard to attract the right woman and keep her in the relationship. The key to succeeding in this goal is when men feel good about themselves; it starts when a man looks inwardly and make peace with himself, acknowledges and loves who he is. It’s unfortunate that for many years men were told that it is unmanly to cry or show vulnerability (like the need to feel loved and needed). Somehow ignoring their emotions became a masculine trait. But when it comes to dating and relationship men need to be in touch with their emotions and needs, to be able to attract the right person. Once men feel confident in their masculinity and yet stay connected with their inner being I think it will be a wonderful world. It will be a world where both men and women are able to communicate honestly in a kind affectionate way, and feel safe to open up to each other. 

Veronica Alcanda - Alcanda Matchmaking, Spain

My recommendations as to what challenges are men encountering when searching for a life partner are based on my Clients’ exposures (European high achieving men and women). Therefore, I speak for both, not only men, as there are little differences in their expectations and requirements when looking for a significant other. These challenges are:

Exchanging roles
Usually, men want to be somewhat in-charge, at least in co-charge and, even when women treat them as equals, it’s hard for men to see it that way due to their mind conjures insecurities. Thus, dating high caliber women requires some rethinking of male-females roles on the part of men.

Expected monogamy
Most of the time, women expect a monogamous relationship before men do and men need to understand this, since we are assuming both are looking for a “long-term” relationship.

Beauty vs. Brain: a dichotomy
Men usually look for beautiful women rather than brain while women can often be more attracted by charismatic personalities. These traits don’t have to be exclusive. However, it is important to realize that beauty fades away while the person within does not.

Understanding their needs
Professional women find maintaining love relationships a major challenge, and as a result many executive women remain unmarried or unable to be in a committed partnership. Men need to understand that high-powered female executives are built differently; they are a go-getter, a time-keeper, with an idea of making a foundation for betterment of her and her family.

Age difference
Usually, men are the ones who require much younger women but they need to realize that the higher the gap the greater the differences between them thus, the probability of success of their relationship will decrease proportionally for obvious reasons.

The bottom line is men who wish to establish a long-term relationship with high achieving women need to be confident; they need to know themselves; accept themselves and their insecurities; and do the same for the woman they want to interact with. 

Mairead Molly - Berkeley International, Global

Men are clear on what attributes they are looking for in a partner, which makes things easier from my perspective as a matchmaker. However, this can prove to be more problematic in the wider world of dating. By having a clear vision of their desired partner, men are less accepting of any deviations from their ‘dream woman’, creating challenges on their quest for a soul mate.

A substantial number of my clients come to me post-divorce. Knocked confidence can be hard to regain, particularly as men feel they have ‘failed’ with their first ‘soul mate’, so place higher importance on finding the real deal. This often translates as men trying to get back what they have lost, pursuing younger models. In reality this is not always the best technique.

There are ways to ease the challenge of dating, not just for men, but for both parties involved. My advice - don’t overthink things – if you stay cool and calm you will portray yourself well. In the same vein, don’t put on an act. If you are not yourself this will only trip you up further down the line. Your falsities will be exposed with your relationship based on dishonesty. If she doesn’t like the real you, you are not true soul mates!

The physical date brings challenges in itself, particularly for men and the expectations placed on first dates ‘rules’. The most important piece of advice – don’t judge imperfections (I’m sure you have some yourself!). To avoid the awkward minefield of which party should pay, I do advocate being chivalrous and footing the bill. This gives a great first impression and if a woman is really interested, she will be sure to split costs as your relationship progresses.

My final tips on your search for a soul mate - don’t take yourself too seriously and don’t try to find the ‘perfect’ match. Lighten up and appreciate what you do have instead of what you haven’t.

Harella Ishai - Doo-Lev, Israel

Not so long ago the gender roles in dating were very clear: The man was the one who was supposed to approach the woman, he was the one who was expected to pay for dinner, be a gentleman and hold the door open for the woman…

Today the picture is very different. Gender roles are not so clear. Some men are still old fashioned with their approach to women on dating, while other men have a more modern gender-equal approach. The problem is when women want to have their cake and eat it too: on the one hand they want their man to be an old fashioned gentleman with all the relevant mannerisms, and on the other hand they want their man to be modern and support their career, cook, clean, and take care of the children. I don’t say that this combination is not possible; after all, life is not black or white. What I suggest is that both men and women find the right balance in life that works for them individually and for their relationship.

My advice to men: be loyal to who you are, and at the same time be willing to be flexible to meet the needs of the woman who is important to you. Be aware of the old fashioned and modern traits that you possess.

My advice to women: understand that you can’t expect a man to be all, both a perfect old fashion gentleman and a perfect modern man. Most men today possess qualities of both archetypes to a different extent.

By saying all the above, I still believe that the traditional courtship process does good to romance. I do recommend that a man should pay for the date and call/text a woman afterwards to tell her how he enjoyed her company; even feminist women enjoy that gesture.

Julie Ferman - Julie Ferman Associates, Los Angeles, USA

Today’s modern day woman is very confusing to men. She wants to be with a man who’s bigger and stronger than she is, secure, masculine, a take-charge person. But she has a hard time letting him, because she’s been taught that she should be independent. She may make the mistake of “leading” with her masculine side, but what she really wants, underneath her tough exterior, is to be with a man who will lead her, so she can relax, receive and be the vulnerable and feminine woman she yearns to be.

In order for love to occur for two people, there needs to be interdependence (rather than independence): The stronger, more masculine, take-charge he is, the more feminine she will be and can be.  And the reverse is true too – the more feminine and receptive she is, the more masculine he is likely to be. It’s a chicken and egg thing… and someone needs to go first.  Make sure it’s YOU.  Don’t wait for the right circumstances to step up to the plate to be The Guy. Just step up. Practice stepping up, with confidence, knowing that you are enough, that you are indeed The Guy.

Women don’t want to have to chase – so men need to pursue – What to do? Catch her eye, smile, walk up to her, talk with her and if she seems receptive, ask for her number, invite her out for a drink. Don’t be too touchy/feely, or she won’t trust you. Pursue her and ask questions from a place of sincere interest - not just because you find her to be attractive, but because you want to know more about her, from the inside out. If she’s not receptive, or if she’s disrespectful, then she’s not for you, so just move on – no hard feelings.  The more practice you have at this, the “smoother” you will be.

Jane Carstens - Matchmaker for Hire, Vancouver, Canada 

It’s hard to even imagine the perils men face today when searching for their soul mate. In a testimonial format this specifically addresses a couple of sticking points that one man, Drew, is saying while dating in Victoria BC Canada:

“Fastest way to get blocked from a woman's fb wall: jump into a male-bashing thread to dare suggest that perhaps it would be a nice to return to the days when people were friendly and honest in the "real world", and perhaps that guy just thought she seemed pleasant.

My crime: daring to suggest that a guy who, and I loosely quote: "creeped me out for daring to catch my eye at the gym". It was her pet peeve, the world was ending because a man dared to engage with a smile. Holy crap. So much for a yoga lifestyle she purports.

I must admit to being tired of the ridiculous amount of rules and regulations a man must adhere to in order to not offend anyone in today’s world. We walk around as suspects all day long, and dare we look at a woman to smile, lest we be regarded as, in her words, a creeper.

And yet, so many seek an honest, outgoing man who is not afraid to go after what he wants. I expected to be blocked, but I was ok with that, as I do not want her kind of energy in my world. If anyone knows of a country in this world where equal social footing is found let me know.”

What does this tell us, other than the obvious, it’s tough being a bloke... said no one ever!

Shannon Davidoff - Perfect Partners, South Africa

One of the first things many guys passionately exclaim on the first contact with me is: “Please tell me you have NORMAL women on your books! I want to join your database/network because I am so tired of what I find out there – maybe you can give me a different experience to help me find my life partner, I am NOT desperate, I really crave a committed relationship please!” When I ask them to describe their experience with dating women - the common responses are:  

-       Women are too busy to give time to a man except at their command, putting careers, families and even pets before me, no work/life balance.
-       Many are looking for a meal ticket or an ‘escort’ to gad about – with no emotional contract, they are ‘users’.
-       Often they are emotionally unavailable and give us no sign they are ‘available’ so we can approach, many women have forgotten how to flirt (hey, give me the ‘long stare’ so I know you are open to my approach!) but some hunt aggressively not giving a man a chance to court.
-       Many women simply do not make eye contact to connect. Women have lost their feminine goddess and confuse their power and success with masculine power – I don’t want to compete on my own field or date a ‘buddy’ but I do enjoy strong and confident ladies if they remain gracious and soft with me. 
-       Some women are totally OTT and zealots, fanatics and high maintenance – creating drama at every turn, out of touch with fact and logic! (Vegetarians, tree huggers, esoterics etc., are mentioned because they try to impose their beliefs).
-       Some women are dead boring and make no effort to hold a conversation (do they just want to go straight to the bedroom?) or they talk too much never giving a guy a chance…and many women make me feel clumsy in my attempts to court.
-       I am surrounded by women who have no pride in their appearance – short hair like boys, ‘sensible’ shoes (what happened to sexy high heels?), no grooming or style and worst of all, allow themselves to be unfit and overweight! Many women over 35 have turned into frumps.
-       Modern women are impatient with old school courtship where truth and trust can build first. Women have lost their sense of humour! I am hardwired to cherish and adore the lady of my dreams but women seem to keep looking out for better prospects (ala online dating, FB, social media, Tinder, etc) never giving me a chance.
-       I will take sex if offered on a plate, but I really want an exclusive, loving relationship, not a player.
-       I want to feel I have EARNED her love because she is WORTH IT, not because it is a woman’s right, she needs to appreciate my efforts. Women judge most men from past bad experience, never move on, don’t give me a chance, often blaming and shaming me from the get go. Women who behave badly can expect to be treated badly (aggressive, demanding, opinionated, loud, rude). I think I am winning then she drops me with “let’s be friends” never telling me what her expectations really were.

The saddest question all the bachelors ask is “Are men obsolete and needed only for breeding, financial comfort or sex these days?”  

The old adage that says “Men give love to get sex, women give sex to get love” is untrue. Men actually can be very romantic and actually do believe in love and permanent relationships. Men ADORE women, no matter women’s lib or power and independence, they want to admire, protect and love – but women must be feminine and be receptive to love – and sex! If a man’s libido is damaged – he has lost his reason to step up, ever, then expect a mouse, not a man!!

Yvonne Allen - Yvonne Allen & Associates, Australia

There is no doubt that relating to the female of the species can be confusing for guys when it comes to dating…and vice versa!

These days the supposedly innate flirting complex seems to have gone missing! Guys often say they don’t know whether to approach a woman. It seems many women develop a protective persona that conceals their more feminine and vulnerable self in the workplace – and beyond.

It is not surprising that men can often lose interest if a woman they’ve started dating texts or calls too often…their brains has evolved over millennia to assist them to focus on a task and to be ‘the hunter’. While a woman’s hormones may drive her to want to communicate and connect, a man is likely to be more aware of his feelings through missing her than constant contact.

Single women aware of their biological clock ticking often raise the issue of their desire to have a child during the first few dates – even when they know from his profile a man’s views re having children. This is likely to turn off the guy who feels wanted more as a producer of offspring than for himself!

Sex early on can be risky business. For many a woman it’s likely to pump hormones that bond her emotionally while for a guy it may be just an enjoyable physical release.

Appreciating gender difference is key to a great relationship!

Belinda Leung and Beth Harvey - Muse&Co., Seattle, USA

Both men and women have their challenges with dating today. But men have some very different pitfalls. Instinctual male courting behavior has been made moot in a world of socio-economic equality. Men’s natural drive to provide, protect and procreate can be interpreted as chauvinist, or condescending in a world where women feel they want equality, including in the realm of dating.

While equality has helped women become more educated and fiscally independent, it’s toppled the dating framework for men. Left on their own to recreate their own framework, men have constructed one based on fear of rejection, leading us to:
- The decline of a man’s approaching/asking out a woman at a coffee shop, gym, or grocery store
- An increase of men initially meeting women ONLY via apps or online dating sites
- Men using email or text to ask women out
- The rise of the “flirty texts that fizzle” because he never asks her out

Those men who act fearlessly and embrace some of their more primal courting behavior are likely to experience more dating success (as well as rejection) simply by connecting with women in person. Ultimately our instincts will drive who we are attracted to and with whom we’d like to mate. So if you’re single, help courtship along by embracing your femininity or masculinity while dating. It will help make the other gender more attracted to you, and perhaps make your dating life more successful.

Karen Mooney - Sara Eden, UK

Since I started Sara Eden Introductions in 1988 the world of dating has changed beyond belief. Men don’t know if they should be macho and masculine or more in time with their “feminine side”. Should they offer to pay for a meal or should they suggest the bill is split?

There are no clear steps to follow as there were in previous generations. Go back in time to the 1950’s boy met girl, they married, she stayed at home to raise the children and be a good housewife whilst he went to work to provide for the family. Wow how times have changed.

Dating in 2015 style could not be more different! Women now have equal opportunities; they can have careers and financial independence and can also delay having a family until later in life. I feel sorry for men today, just how should they approach the dating game?

My advice would be DON’T RUSH: take time to get to know your date, find out about her goals for the future. We all know people who have said if only I had met him/her now rather than a year ago, the timing wasn’t right then but now it would be.

It is vital your potential partner is at the same life stage as you, sharing similar goals for the future and having similar values are vital for a successful relationship.

Lastly, TALK CHILDREN: in my 27 years as a Matchmaker I am always dismayed at the number of people who are in a long-term relationship and don’t talk children, then suddenly find out having a family is not on their partner’s agenda.


  1. Hi Anat,

    That was a tremendous idea of yours. A beautiful article, and I could imagine the matchmakers present their sales pitch...
    Undoubtedly, you emphasized the sentences which needed emphasis.

    Gracefully done Anat. L'chaim!

    Susan Alper was a little dramatic with the "extremely difficult" as if our genders generated mutations and mutilations, or any other physical abnormalities recently took place without informing us...
    But until not so long ago, men weren't so much in touch with their emotions and needs and gender roles were pretty obvious.
    As It might be good to be in touch with your emotions and needs, it also could be the quickest turn-off in a relationship because "needs" are not attractive and never were.
    that's why gays and girls get along so well... they're all about emotions and needs.
    Veronica's opinion was mainly concerning high rank women challenges, but they always needed their space and independence, so I failed to see how her words reflect our present. it just stands to reason that these women will develop that behavioral pattern.

    Mairead Molly hit the jackpot with her agenda. She really reflects the biggest true challenges today. Excessive thinking and masking through screens (both physical and emotional layers).
    I heard Harela Ishai speaking with codes. Finding the right balance, well, that's true for almost everything in life. I agree with her last advice, regarding the traditional courtship process. She's right. Even feminist women enjoy that gesture and probably many more (money related) gestures;)

    I took Jane Carsten's story, as a standard deviation. That hardass yoga chick can be replaced with many other prototypes, and they're all considered minority and it's better to leave them be. As Julie Ferman said earlier, "practice stepping up". Rejection is inevitable and it's better than regret.

    Shannon Davidoff is brilliant and funny. That's what I've been really waiting to read from the beginning. it says almost everything. Except forgetting the coin's other side. Women have a parallel repertoire.

    Yvonne Allen's advice about sex early, is kinda difficult for both sides, mainly in these days. Sex in a later stage might also frustrates both men and women. Great expectations can easily lead to greater disappointments.

    Beth and Belinda repeat Julie Ferman's in other words. The self explanatory failure to grasp the true needs of women. So much demand and yet, not even close to enough supply.

    And lastly, Karen's "talk children" advice is crucial. While I disagree with her opinion about the present days (like Susan Alper), I couldn't agree more about the "talk children" part.

    If I would have to summarize our challenging sad reality nowadays, in one word, I'd say: Screens! (For Heaven's sake, take your eyes off them when you're meeting someone)
    Social networks and web comm behind the screens is a powerful destroyer of real natural human connection.
    it's the dissonance one needs fighting, whenever enters the dating arena.... out and far away from the screens' comfort zones, life begins...
    Women's and Men's needs did not change much. We're still looking for the same. Technology changed drastically.that's why we see so many paper tigers. Men and women feel protected by their screens. Alter persona is easily nurtured and grown this way.
    Julie Ferman's "No poses practicality" is really wonderful because she actually touches another Screen-Age symptom. Cowardliness. Those screens men and women hide behind, supply them shelter from the outer real world - the true reality. Behind the screens they carefully build their remarkable "shine bright like a diamond" dating profile, but when the time comes, the alter profiles stay on the web and soon, true characters reveal themselves...

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