How to approach a younger man

Breaking the Ice - the latest "Cougar Talk"

The bottom line is that younger men are often shyer and more intimidated by older women and much less likely to make the first move. This alone makes the start up of a relationship with a younger man more difficult for most women. Women still generally have hang-ups regarding being the initiator for a first date and sometimes even a first conversation. I recently heard from a reader that she had significant eye-contact with a younger man and she felt he had “preened” for her. Nothing happened. She waited to see him again and it wasn’t until much later that she made facebook contact.

The key is immediacy. Most men won’t remember a significant “eye-contact” moment a day later, much less a week or a month later. Everything moves faster in the world today including the dating dynamics. Women can remember that special moment weeks or months later, but men may have missed it completely or forgotten it quickly.

Nowadays you have to take advantage of opportunities at meeting someone as they happen. He could be single today and involved tomorrow, so why wait and risk that opportunity never presenting itself again.

Now many older women have plenty of self confidence, but are just out of practice, or they feel it’s not “proper”, or their ego dictates their inability to cross that line. Each woman must confront those demons and analyze for themselves what their personal reasons are for not acting on an opportunity.

Then again, I am obviously not talking to those “stereotyped” but very real prowling “cougars” who can give “cougarism” a questionable reputation. I’m not discussing women who just want a quick roll in the hay and will approach any young thing that crosses their path. I have heard from plenty of younger men that have been resentful of older women because they felt they had been used, their emotions toyed with and then dumped with no explanation. Younger men can be just as emotionally involved as the woman, if not more so. Many have a fascination with us because they believe they won’t encounter the same mind games, immature thinking, and sexual hang-ups that they are frequently faced with when dating girls their own age. By the way, not ALL older women are emotional stable or incapable of mind games.

The point is, if you find yourself interested in a younger man that crosses your path you usually must make some sort of first move. Just engaging him in a longer conversation works, then let him know that you find him interesting and would like to get to know him better.

On the internet, it is less safe but you have more exposure and more opportunities to meet someone. It is, however, just as much a hit and miss as trying to meet anyone of any age via the internet. You never really know who is on the other end of your virtual world. You can only believe half or less of anything anyone tells you online. If you’re intuition or gut feeling is active and usually accurate then listen to it and add a good dose of common sense on top of that.

In person, I have found that finding you have something in common and inviting that man on an adventurous outing (exposing him to something he either loves or has never experienced) to be the easiest and most effective way to get to know him. If you have access to a boat, you tell him you know he loves fishing, would he like to come along. If he likes golfing, you let him know you got two passes to a great golf course, would he like to come along (add you could use a few tips, if you like). You were given two tickets to go ballooning and no one you know is courageous enough to go with you. However, in a pinch, just asking a man if he has time for a cup of coffee works just as well. Or if you know him a little already, asking him to come over to help with a “manly” chore works wonders for both boosting his ego and giving you time alone.

• Installing electronics
• help with a computer
• fixing a gutter, spotting you while you clear the gutters
• saw off a limb on a tree
• help lift or move a couch
• any other lifting, fixing, moving, installing project

Remember the golden rules of dating in general:

• Make him feel good about himself
• Don't ever make yourself seem superior
• Trust your gut (unless you are usually wrong - then trust a friends' gut)
• Men usually like skirts and heels - not required, but definitely an advantage

Early on:

• Be yourself, but don't talk about past relationships
• Don't tell all your dark secrets or faults
• Keep eye contact
• Don't pursue hard if he doesn't give the right signals - you're not desperate
• Always date in public initially and give a friend all the details
• Get enough information about him to give to a friend to find him (safety tip)

Just remember that regardless of whether it's a younger man or not, be true to yourself and to them. Yes, put your best foot forward, but don't be someone you're not and always make the other person feel as you'd like to feel. Anyone younger has to be helped to feel self confident, that's just natural. Do that, and BE confident, everything else will follow.

Why Adult Dating Sites are so popular

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Do's and Dont's when dating a younger man

I've learned the easy and the hard way what works and what doesn't when dating a younger man.


First and foremost you must be flexible, and I Don't mean just your limbs. That is a plus but not a necessity. I mean, be mentally flexible to embrace new ideas, music, literature, interests, even vocabulary. I"m not suggesting that you have to change who you are. Please remember that your attractiveness is precisely the fact that you know who you are and what you want and don't have to conform to society's preconceived standards. However, part of that definition is not being tied to one generation's definition of what's is "in" or interesting.

My first experience in this regard was in respect to music. Admittedly I was fairly rigid in my love of music and had not explored new music for 20 years or more. Like many of my generation, I felt "my" music was the best and nothing since could really compete so why bother listening. Let's face it, the headbanger, hard acid, lift me over the floor and pass me through the room and over your head music, went right over my head and I hadn't paid much attention to it since. I didn't even pay attention to rap because I felt it wasn't really music and quite frankly, was beneath me. Well, I was proven wrong when I was immersed in it over a couple of drinks and my partner explained the nuances and we sang the songs together and danced with abandon. I totally enjoyed it and began to listen to a whole new repertoire of music that I had ignored for so long. Needless to say, I had a lot of catching up to do. The fact that I was open to listening was appealing to my partner as it proved he had a lot to share with me and I had something (quite a lot) to learn from him.



While I was teaching him to dance, he was teaching me new tunes to which to dance. He got quite a kick out of looking up tunes on itunes, downloading them and then getting my opinion on them. I learned what his favorites were and I found some of my own. I also opened up a whole new door at work. Whereas in the past I had little in common, musically, with my young employees, I now knew exactly what tunes to pick for our awards banquet videos. I was suddenly a hit with all of them. It was also amusing to see the look on my colleagues faces when my phone rang and it was a popular new tune (OK - it was Low, I was pushing the envelope).



Now when I mention vocabulary I do not mean that you need to use it yourself. You probably will end up looking very silly and sound even worse. But you should know what that vocabulary means. Do not be afraid to ask, your mate understands that you aren't going to be exposed to most of his peers' secret language and will get a kick out of teaching you. Furthermore, it doesn't hurt to remind him the proper usage of the language in case the slang gets out of hand and crosses over into the professional world. Just remember, you are not his mother and correcting him like one will quickly cool the embers. Above all be there to build his self esteem.



Learn what's new in the world in fields you are unfamiliar. If he's into finance, as is mine, then learn what's going on in that field or have him fill you in on the highlights.. Better yet, keep up with a few companies or stocks on your own and update him on what you came across. Whatever his hot buttons are, take the time to learn a little about it so you can engage in conversation in his favorite topics. Believe me, it'll pay off. He will return the favor, I promise.



Sports! You can never go wrong with knowing a little or a lot about sports. Most men, not all, have an interest in one sport or many and the more you can share the interest the better. Besides, there aren't many negatives when watching tight ends or skimpy uniforms on men while they are battling it out on a playing field.



Now here comes a big don't. Please don't expect him to take you to parties that are being thrown by his high school or college buddies. Not only do many younger men not want to be "outed" as a cub to all of their peers (especially the women - they can be hostile), but they really don't want all of their buddies hitting on you. Let's face it, younger men are shameless when it comes to ignoring a date and hitting on anything female that walks in the door. He doesn't want the competition and will want to avoid that. Do not take it personally, it's just one of those things. Now if you are married or a long term committed relationship, and he's still uncomfortable, then I must admit I would ask him what why he feels that way.



Don't ever belittle him because of his age. He could feel insecure enough knowing that you are a smart experienced woman, but it's the differences that are to be celebrated not pointed out as negatives. Of course, there will be areas that you are more knowledgeable about, but that is not his fault and shouldn't be pointed out as such. You are there to support each other's positives, not point out each other's negatives. If you open that door, you will lose for sure.



The biggest positive I have found dating younger men is there capacity for appreciating your successes and talents. They are supportive and can be your biggest cheerleader. You need to return the favor by making sure they feel the same appreciation and support. If either of you isn't getting that from your partner, you should move on.



There are many other Do's and Don'ts and I will share them with you in future editions. In the meantime, if you have any observations of your own, please share them with me as I'm always looking for good information from which to learn and to share.

How Cubs rate Cougars

Well, lo and behold, the cubs have their own rating system for us cougars. I know women hate to be rated, but let's face it ladies, that's what men do. Furthermore, we have our rating system, but we try to be more discreet about it and often disguise it some emotional explanation. Let's get real. We have deal breakers that are sometimes more arbitrary than those men have.


However, I digress. We are now talking about the male perspective only. I will make a traditional list as they do from A to AAA+++ at the conclusion, but I found the subtleties of their rankings to be to important to ignore. Therefore I didn't want to only make it a crass list with firm designations. It appears there are a group of factors that push you up or down the list so there is not hard and fast definition of each category. The factors are as follows:

Does she hide you or sneak around with you? The more open she is the higher she rates. This can have a direct correlation to whether she is married, but not limited to that. She could be embarrassed, has disapproving children, jealous exes etc.

Does she have time or can make time for you easily? The more flexible she is, the better. Men don't want to have be required to spend a lot of time with you, but they want you to be available when they chose and for however long they chose. The more able you are to accommodate that perfect world of theirs, the higher she ranks. This is probably the most important factor for most. If she can get a babysitter at the drop of a hat when he calls and isn't working (doesn't have a curfew) or better yet is an ex-trophy wife with lots of money and time, we're talking AAA.

Is she beautiful and/or fit? Obviously more is better here as well.

Does she have money? Do I actually have to explain that one?

Does she have children? Actually not as important as you might think as long as she has a babysitter on speed dial or they're old enough that they don't live at home. Bottom-line, as long as she'll drop everything at the drop of a hat and can stay up all night with you if it happens to go that way, Great.

Is she smart? The smarter - the better.

Is she funny? Humor is important. That goes for both sexes.

Does she allow an open relationship? No Strings Attached? Something all men hope they can have at the beginning. Unless the cub is looking for a long term relationship which is rarely the case at first, the ranking goes way up.

Sexually adventurous? Ah come on, you know the answer to that one..... We're all grown ups here.

Confident? Definitely a plus and almost a requirement for being a cougar.

Successful in her own right? Success is a big turn on.

High Maintenance? If she is needy, self absorbed, high drama, discusses past relationships or talks to much in general then she loses value very quickly.  Any of the above can become deal breakers in and of themselves.  I'm sure many men can add to this description endlessly.

Nag about wanting to see them more or want a commitment? God forbid. You can drop on the rating scale quicker than the Dow Jones ticker during Sept. 2008.

Need to bring your kids to your outings? Do that once to many times and you will find your calls being screened.

All the above factors are based on how they contribute to the FUN factor. Impede the fun = deal breaker.

There are obvious AAAs, but any big deficits in the above categories can pull you down, and vice versa. To satisfy the male need to see a neat definition, I submit the following list.

A  A single or married cougar who can support herself, probably average looking to good looking, who has many family or work commitments that limit spur of the moment plans with whom the cub has a friends with benefits or more relationship.

AA A single/married cougar who is very successful, who can mentor, teach and guide a cub, who's great company and perhaps can even support him financially, if necessary. She is readily available for a good time most of the time, but not always. Looks can range from average to good looking.

AAA  A single woman who has money, doesn't work, has time, is flexible, confident, is open, adventurous, funny, fun to be around and beautiful - The all around perfect woman.

And the controversy begins.....

Well, I certainly didn't anticipate the heated discussions that would arise at my household when my last post was published. And it was about the most unexpected topic. It appears my cub (his term) disagrees vehemently with me about the "sexual peak" of women vs. men.

It is his firm assertion that men do NOT hit their peak at 18 but are at their peak anytime later in life (not including those who have physical issues) and hit it anytime they have someone in front of them that they want to have sex with again. In other words, it is all mental, if they want to impress a woman they can perform anytime, anywhere and with all the impressive vigor or finesse required to make her want to come back for more. Furthermore, their lack of impressive performances later in life is purely a symptom of boredom with their wives or partners. They sowed their oats when they were young, tried all the various exotic twists and varieties and therefore have very little that excites them at that point other than perhaps a hot, young nimble thing that they can lust after. Women (ladies), on the other hand, are handicapped early by the norms of society and are not usually inclined to engage in the free sexual explorations that they might like to because it would stigmatize them as "sluts". Furthermore, with age they become bolder and care much less about what society has to say and can finally make up for lost time.  Finally, women are now in a unique position to do as they like and get away with behavior that, as he puts it "if I did that, I'd be labeled a pig".  It's a cool trend now, according to him, to be a cougar or a cub. 

Now I really thought I was on firm ground, medically and psychologically, when I made that "sexual peak" comment.  I still believe it, but I have to be open to the possibility that his argument could hold some merit.  I mean, I see major holes in that theory but one has to give pause and ask yourself "Do men really think this way?".  Is this just a minority opinion?  Or is this a pervasive impression that men have?  I'd really like some feedback on this.  Could men just have trouble with the thought that most of their lives they are losing something while women are gaining?  Or is that just a self serving concept for women? 

First experience with a cub

I thought I should share my first experience with a much younger man.  It might give you some perspective on both the positives and the negatives.  And yes, despite the negatives I did not make it my last. 

I had a normal match.com account to which a very young man responded.  I got the email on one of those days where the world was bleak and I suddenly wanted to throw caution into the wind.  I find that although I get many inquiries, I'm really somewhat of a hard catch.  I love my solitude and my own company and it takes a lot to get me out of my shell.  Don't get me wrong, my co-workers, employees and friends will tell you I'm the life of the party.  But when it comes to dating I'm very careful and at the time could take it or leave it.  Work was so all consuming that quiet times were a welcome retreat.  But sometimes you just feel spunky or adventurous, and when I feel adventurous - watch out.  So I met this young man.  I'm embarrassed to say he was a mere 24 years old, worked for the airlines and was just so so hot to meet me.  We met at a local sports bar.  Lots of people, always trying to be safe, I ventured inside and he spotted me almost immediately.  To say he was feeling amorous is quite an understatement.  He had real trouble keeping his hands to himself, and I'll admit I was flattered.  It was nice to feel that attractive and desired.  I will also grant that we probably didn't have much in common.  His level of sophistication was very low and honestly there would not have been much hope for improving it anytime soon .  Oh well!  What he lacked in sophistication he tried to make up in enthusiasm.  His confession, months later -that he was the most envied man at his workplace, is probably accurate.  He apparently conveyed his experiences in detail to his co-workers much to their delight.  Frankly, he was energetic and wanted to prove he was worthy.  He literally would call me and beg, "please let me come over again, I promise I'll try to keep up this time". 

Sure - it didn't last long, but it was a learning experience for myself and obviously for him.  I ask myself frequently why God would design us in such a way to make a woman her best after 40 and men their best at 18.  It sounds like a cosmic joke.  Be it as it may, that's reality and we have to come to terms with it - each in our own way.  I've learned a lot since that first experience.  Primarily that you can find true quality experiences with a younger man that transcend the more obvious advantages.

I have, however, found a lot of other pitfalls that I want to warn you about.  The primary ones are as follows:  The stalker, the Conman and the younger man at work.  I haven't had experience with the latter one  because it violates one of my golden rules, but I have enough third pary stories to curl your toes,

Cougar Tales

Hi, I'm Isabella,

It seems that my friends are determined to make me share the experiences I've had with the younger men in my life.  I was blissfully ignorant of my rising stature in the world of cougars.  The word used to bother me as I felt it had the connotation of being predatory, but I've since come to terms with it.  It is what it is, a name and let's face it, it's an attractive animal so why fight it.  My 28 year old companion informs me that he is a cub so I'll take his word for it.  And yes, before you start, he is a little younger than I am going to recommend.  But there are exceptions for every rule and he is an exception. 

It is not that I came to be this icon of cougarism, it all happened very innocently and without forethought.  Women in my age group know the unfortunate truth.  Good men our age are rarely single and if they are they either have issues with performance/endurance, are selfish, have no humor, live with their mothers, have addition issues, are workaholics with no time, and most importantly usually make less money than me.  This usually translates to a range of reactions from outright hostilility or fright to them having a vague sense of feeling uncomfortable.  If they are as financially successful, as I am, they want a trophy wife or mistress (by definition very young).

Believe me, I've been to enough of those Executive Retreats with all the VPs etc. running aroung and checked out the women.  They were a few long term wives there, but mostly it was a sea of young blondes with very large breasts.  So the question becomes, do I sit on the sidelines hoping for the perfectly appropriate man by society's standards or do I get in the game.  For me, I found that the traditional online dating sites brought out the younger men and although I didn't actually take up very many on their offers, it did open my eyes to a whole world of adoring men out there that want a chance to be with a quality woman who doesn't play games, bring drama into their lives and have so much to share with them.  There is more than one young man out there that has become a successful and polished businessman because of how I helped develop the best sides of themselves.  It isn't just about the good sex.  It's about having someone by your side that truly admires you, encourages you and brings out the best in you.  In return, they have a champion to build their self esteem, polish their image with a healthy sheen of sophistication and give sound career advice.  There are no losers, especially if you have the proper expectations.  I'm not necessarily talking about finding a husband or even a companion for the rest of your life, although there are many instances where this is what is found - take Demi Moore for example.  But instead, making a friend of your lover and sharing two different worlds and finding a new one together that melds the best from both.

I will be posting many of the detailed stories of my funny, sad, eye-opening, sometimes humiliating but always real experiences and hope I can impart some insight for both cougars and cubs out there.  For the rest of you, enjoy and live vicariously through my experiences.  You're bound to snicker and laugh and occasionally raise your head in disbelieve and call out.. "hey honey, you're not gonna believe this one!". 

I also have three young men (late 20's) that work out of my house so I get to hear the male perspective all the time and I'll share those nuggets with you when I can repeat them.