Men of a Certain Age: Things I Learned While Dating an Older Man…It Ain’t Easy.

June 27, 2012  |  

By Valerie Jean-Charles


A few weeks ago, a conversation emerged on my Twitter timeline discussing whether or not black women should seek older men for dating and relationships. Many young women may hold the belief that an older man will be more established in his career, more protective and eager to settle down with one woman. Yet, as someone who has dated older, I now know this is not always the case.  There are a few major differences in the way that older men do things that any young black woman should respectfully consider before embarking on a May-December romance.

One of the first factors a woman should weigh is that an older man may not be as mature as she might assume him to be.  The general assumption is that a man of a certain age will be very mature, what with the assumption that he’s gotten all of the partying and “playing” out of his system. A man should be judged individually for what emotional and mental state he presently is in, not for where society dictates he should be at a certain age. My experience has taught me that there are plenty of men who are well into their 30s and 40s who still possess the behavioral traits of an early-20 something, college-campus playboy.  Unless you are looking for a fun and light partnership, such a man – regardless of age – is not the type to pick when ready to settle into a serious relationship. Trust, the old saying, “with age comes wisdom” does not apply to everyone. More or less, the experiences of a man can be what makes him more mature, or what has him getting his Benjamin Button on behavior-wise.

On that note, another major difference that is sure to arise is the large gap in life experiences. Although, a young lady may feel as if she is too mature for men her age, her lack of experience will more than likely cause her to come off as young, inexperienced and even immature in front of an older man. Let’s face it: the things we experience by the time we are in our mid-20s will pale in comparison to the journeys and obstacles we will have endured 10-20 years down the line. A woman in her 20s can only act as what she is – a young adult, no matter how mature she is. Such a difference in life experiences can prove to be thrilling at first. He may be invigorated by her youth, while she is enthralled and inspired by his background and knowledge. But the very things that may cause a strong connection, may threaten it. The power dynamic may be more tipped in the man’s favor due to his array of experiences and age. Being older, the man may be more grounded in his beliefs and habits, being less likely to change them; regardless of how they may affect his partner. The younger woman, on the other hand, may grow weary of the adviser role the man may assume, feeling as if he is being more condescending than mentoring, more stubborn than willing to compromise.

Lastly, a woman should consider if she is ready for what she is asking for in a relationship with an older man. She may feel as if she is ready to settle down, when in actuality that may be the farthest thing she needs, and even understands. An older man may be at the point in his life where he is ready to find a wife – and not just a girlfriend. He may be hoping to get married in a couple of years, with babies soon to follow. A younger woman must really ask herself if she is truly ready to experience such life changing events, and willing to give to her significant other what he is asking for. On the other hand, there are some older men who have already been married and have children, and may not wish to have anymore, or go through the experience a second time around. Because of that, they might want to take things at a snail’s pace. A young woman should weigh whether or not she is ready to make such definite decisions that may affect the rest of her life and alter plans she’s had for herself.

I am, by no means, slamming or demonizing May-December relationships. As I have learned in the past, they can be both thrilling and daunting, and some can be a big success. It all depends on the guy. With more and more articles continuing to question the marriageability of black women, I understand why some may look at men they may not have considered before. And I do advocate for women to keep their choices open as love is such an indiscriminate force. However, I do ask that we keep our heads leveled when trying something new, especially when picking mates who are more seasoned than us.

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    This a good article. I have experience both sides. And you pretty much nailed it. I found that dating no more than 2 years in either direction worked out best. You are from the same generation, and for me I found have more things in common.

  • Pingback: Should Women Seek Out Older Men for Relationships or Is it a Bad Thing? | Naturally Moi()

  • May

    Im 27 and my husband is 43. Every where we go we get stares and laughs and negative commentary. Its annoying because we cant even enjoy a day out because of the rude people, but they are never going to stop. I’ve been with him for 4 years. We have ups and downs but I am happy for the most part so i just deal with being the butt of some ignorant irrelevant stranger’s jokes.

  • Wow

    age and maturity don’t always go hand in hand when it comes to men.

  • Mariposa

    What about stamina older men can’t always hang. I’m an older woman that prefer younger men. Our energy levels match perfectly!

  • commonsense

    I dated an older man almost a year after a relationship with a man in his late 20’s. All I have to say is the older man was silly and make sure they have plenty of Viagra on hand. I was use to twice a day instead of once every blue moon. He could never go another round.

  • Trisha_B

    I’ve always had a thing for older guys, idk, something about a MAN rather than a boy. While i didn’t go for guys that had kids my age (rocsi & eddie), i went for guys who are like a couple of years to 10 years older than me (Bey & Jay). I had the thought in my head that i don’t want a boy, i want a guy w/ wisdom, a guy who has his stuff together. Well not all older guys have the mentality to match their age. I was 20-21 dating a 29 year old, he didn’t have his stuff together. He was like dating a 18 year old. He didn’t have a job, was bumming it at my dorm room apartment, & since he still wanted to run the streets he’s back in jail. when we would get in arguments he would always tell me i don’t know anything b/c i haven’t experienced anything & he has more years on me -___-. Well i’m 22 now and the guy i’m seeing is 21, he’ll be 22 in a few weeks. & he is more mature & has his stuff more together than a lot of grown adults. He has job that pays him $24 an hour, he lives by himself, & he’s meeting w/ a Realtor to buy a house in the coming months. My point, every man is different. There are the same amount of grown man who are mentally immature that there of younger guys that mentally mature. If you like older man, then do you. But don’t go into it thinking all your problems are gonna be solved and he’ll be everything and more b/c that may not be the case

  • I recently had the experience of finding out that all older men are not as mature as they look or appear as the article states. My advice is get to know him and make the judgement whether he is the best fit and match for you.

    • SHAY

      Your right on Nicole! Many men swear to be so mature, when in all actuality they’re looking for young, immature “Arm Candy” that they can run circles around. They don’t mind spending as long as you don’t mind NOT being taken seriously.

  • beautifulglenda

    I read this and now i dont know what to do!! On one hand im 26 and i haven’t been able to find a man my age group who wanted more that whats between my legs and at this point in life im far from looking for that. So i decided to look for older guys that may want more but reading this article made me really think. What do i do now??!!!

    • IJS

      if ALL the guys you’ve come across only wanted sex, the problem is not the age group of the guys you date…

    • shay

      Stop purposely looking for him, he will find you. Older men tend to enjoy outdoor activities so, get ready to start jogging or reading in the park. There’s nothing wrong with mixing it up. I have always dated older, and one thing about older men, is that they like a little competition (Just a little!) If you are near the downtown area, you can find a vast array of eligible men out having lunch. They LOVE to be seen showing off the new shirt, shoe, tie look! So I encourage you to make yourself available for TUESDAY or WEDNESDAY and have quick bite out (and don’t forget your book). Don’t dismiss all of the young one’s; some are serious about giving the older man a run for his money AND his woman.This is what I mean by mixing it up! Just have fun, hit some concerts and festivals. Allow yourself to date more than one man at a time…it’s only dating. The most important thing to remeber about older men, is that they love to laugh- life is not that serious to them. So I hope you’re witty and not insecure.These type of men draw many women so, enter at your own risk. Enjoy the chase!

  • Veratta Pegram-Floyd

    Dating older is really no different than dating younger or the same age…it really boils down to personal choice and where individuals are in their own lives when they pursue relationships. The issues listed above can happen within any relationship; age is not the common denominator that will define a dating experience.

    • Z


  • Suga

    I date men in my age , 40 and up….I think the men thats looking at older women ,the women are mature, secure, and have their shyt together, their chilled , no drama, or craziness going on…With…. some….. of the younger generation its a lot going on in the dating scene…to much playing around and having unprotected sex on male and females behalf…drama of all kinds, including daddy and baby mama drama, fighting…..Some…. younger people is just wild and they are not thinking of getting their shyt together….this is playtime for them until they get in their 30s to mid 35 and up…Which most dont understand that they can have the career ,house ,cars and still play around …Some younger generation has wised up to the fact..The main thing is having peaceful, relaxing surroundings around you when your at home….Which most older male and females have…thats the attraction…along with other perks..

  • Jan

    I have been dating an older man for the past 6 yrs and yes we are still dating.. I love him to death but he is the most difficult person I have evermet. Very smart, but very immature and selfish. His behavior is that of a college student. I have dated younger guys that are mre maturer than he is..

  • kadietweets

    I’m in a relationship with an older man and I’ve never been so in love. he’s mature, respectful and supportive of my aspirations. It all comes down to individual experience.

    • Adedra

      I feel you on that. My man is the sameway.

  • Mrs. A

    That pic of Eddie & Rocsi is creepy…..

  • MLS2698

    I didn’t read the whole article. But stay away from old Kat Daddy’s. Especially one’s with gold crowns on their teeth.

    • Nope

      Reading 5 whole paragraphs is just so tiresome isn’t it?

      • MLS2698

        Yes.Especially if I know, old or young, most women just lay around like dogs with men, anyway. Rocsi is building quite the rep.

  • quest

    I dated a older man once and he thought he was going to control me. Some older men are very set in there ways and that can be unbearable. He used to get off work and want me to come over and he would just sit in his pajama’s all night and watch TV. Talk about boring. I ended that quick.

    • Ay bay bay

      Interesting. Sounds Ike my kinda man.

    • queenietoo

      roflmao omg

  • bluekissess

    Is this article based on personal experience or facts. The older men I’ve dealt with had the problems not me. In many cases the ages should’ve been flipped. MN continues to make assumptions. Just because it didn’t work for you doesn’t mean it doesn’t work.

    • Nope

      Um, couldn’t the same thing be said about your comments….?

      • bluekissess

        Nope. All I want to do is voice my opinion. You can always click on the button by my response if you don’t agree. All I’m saying is don’t write an article saying a relationship of that magnitude wouldn’t work and have a picture of Beyonce and Jay-Z. I think it can work based on the individual.

        The article talks about being mature doesn’t mean your experienced. My response to that is older men can be the immature ones at times. It’s not always the “young one’s” the statement the article made to me was an assumption. Assuming that all the young ones are mature yet inexperienced.

        • Kisses

          Are we reading the same article? Perhaps you’re reading in between the lines, because I can’t find anywhere where its stated that it wont work….and it seems like you’re trying to turn the article into a whole different discussion altogether.

        • IJS

          Reading comprehension? No? Oh ok.

    • MNEditor2

      blue, the title in itself lets you know its based off of personal experiences, and she says that in the end these relationships can be a success, it just depends on the man. No need to throw shade at us, because you’re the one assuming, and you know what they say about people who assume things…

  • Nope

    Another reason women like older men is because those men make them look younger. Generally speaking, once a woman is in her late 20’s men their age prefer younger women, if not before then. But to an older man she’s still young, relatively speaking, because most any man likes younger women. It’s an interesting dichotomy.

  • Amija James

    I dated a guy who was older and he got mad at me and asked me who did I think I was? Jayne Kennedy? Bwahahahahahahhaha. I asked him, don’t you mean Beyonce? He really got mad then.

    • quest


    • Kells

      Funny stuff

    • say what?

      Okay they said older not ancient lol