Do's and Don'ts for dating a younger man

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By IsabellaRothchild

How to not get derailed from a good relationship

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 in a long term committed relationship,he should have gotten over it.  If he still feels that way you might have a serious problem. 

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 othe'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.

Seth Layton profile image

Seth Layton 7 months ago

Hey Jaimie, I know you wrote this 15 months ago but it sounds like the guy you were with was some immature younger guy who still needed to sort out some personal problems. I know that I don't have personal problems myself, and I know that if I ever dated somebody older than me, that relationship would stay strong no matter what. It sounds like he got scared when he saw you with your ex-husband and didn't feel right. I know if that was me, I would've been like ok, no big deal. She's simply talking to her ex-husband. I hope that you're far from over with that situation by now.

R3dcougar profile image

R3dcougar 8 months ago

Much of this is great advice for any relationship, but the specifics for the age-gap kind are spot on. My most recent cub told me that one of the reasons he prefers older women is that he doesn't find himself in the position of having to pay for everything! I appreciated his honesty - and realised that this is probably a big issue with younger women who don't have as much to spare as I do. And the item about not expecting to be invited to events with his friends is also right - and it is true for the cougar as well, that there may be members of one's circle that would be snotty about her bringing along a toy boy. Me, I don't give a flying rat's ass what other people think - but at the same time, there's no point in making your friends take sides. If it becomes serious and you're really a part of each other's lives in a big way, THEN everyone around you will need to adjust to the notion. But not till then.

jaimie 22 months ago

I was involved with a man 19 years younger than me. What started off like I was his soul mate ended very badly for me. I was actually married for about 9 months into a very sporadic meetings with my cub. Although my marriage was very bad and we are now seperated finally. It caused my cub to have a negative feeling for me somewhat as not a good girl. We ended up having a friends with benefits relationship for a year and a half. My problem I fell so madly in love with him and did not know how to do a casual sex thing and often became very emotional and reactive to him. For about the last month things were going well for us as fwb- but he saw me in a parkin lot with my seperated husband when I was supposed to meet him. He got very mad and questioned whether I was ever going to get divorced in the first place- now this was all very shocking to me because he always acted like he didn't care what I did. I have cried and told him I love him which now he sees me as a dramatic emotional mess. He won't even talk to me now. I am really upset- I know this guy has feelings for me. I know it in my gut in my soul and in my heart. I love him more than I can say and want him back. Is there any advice on how I can get him back? It is very out of my character to become so emotional and reactive. I just got lost in the whole experience but I do know I am in love with him. What do I do to win him back and have a relationship on a different level? Is it possible in anyones eyes?

Ludolph L. Misher III 2 years ago

Hello Isabella, I find your hubs very informative and accurate.As a "Cub", I realized a long time ago the Power Of a Cougar Woman.From a Man's Perspective, I have found that women of this caliber have the highest levels of esteem on the planet.This new day phenomena is spreading quickly around the globe and for the timid at heart...well they should stay out of the way of this woman and continue to keep company with the MISERABLES!

amy 2 years ago

my husband actually stated that when he met me, he thought i had money. yes they want experience, or sexually adventurous, and looks, but they want someone with big paying job, which i always had stability there, but they want money money money i am 49, he is 35

IsabellaRothchild profile image

IsabellaRothchild Hub Author 2 years ago

Sure, I'd be happy to explain in more detail. I was only referring to the early stages of dating when no level of committment had been reached and only talking about those kind of ex-high school friends type parties. It really only happened a couple of times when we first dated and he explained it to me later and no, once we had been together for a few months it did not happen again. If the younger man has never dated an older woman before it's a tougher transition for him in the very early days as he gets used to it. I hope this helps clarify my point. If you have any other questions, please feel free to ask. I enjoy your hubs immensely.

lindagoffigan profile image

lindagoffigan 2 years ago

IsabellaRothchild, welcome to hubpages and I have become a fan. If I dated a younger man, I would like to not be left home because of others that may be interested. Do you think that it is a good idea to be separated and not included with his friends. You have taken all of that time to learn new music and I think that it is not a bad idea to learn the other music as well, but I am not too sure of being left home because of the reason you mentioned. Could you explain the circumstances more?

Steven Scott 2 years ago

There are meeting places for cougars and cubs to meet each other.

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