On Dating Older Women


ChickyBabe brought up something I haven’t thought off in a long while. Culture as we have it usually points to older men dating younger women. I don’t know how that evolved from, but I have as it is, a lot of cultures, especially Asian cultures tend to frown on older women dating younger men on a principle. Even as of today where some of us might even call such role reversals acceptable, you can’t deny the majority being younger women and older men.

Personally, I like to think that it’s always a good idea for a younger guy to date older women in the beginning. Not as some sort of rites to passage, but rather as part of the experience that we all go through as we try and make sense this thing called a relationship. And it makes sense too.

Think about it, younger men tend to want to have fun, tend to have absolutely no clue about what women want or how to generally make them happy. Older women tend to have dominance of age, they tend to know what they want and some aren’t afraid to show it. Men don’t mind being led around on a proverbial leash if it isn’t an obvious one. Women don’t mind wielding a leash especially when they know how to. In some odd Freudian Slip of a way, it works.


I’ve flirted around and dated older women in my life. Mind you they weren’t just 1 or 2 years older. They also included going as far 6 to 10 years my senior. It’s not that it doesn’t work. Mind you women willing to date younger men are women worth a shot going after. It’s just that at that day and age, I wasn’t the best kind of guy to be going out with. I knew what to do, I just didn’t know how to do it. Being young, it’s far from dating anyone around the same age, much less anyone younger.

If anything, the most important lesson that any guy comes off with from an older woman is the fact that women, all women, need security. It doesn’t matter if it’s emotional security, physical security or financial security. Depending on who it is, the kind of security that takes precedence varies. It’s one thing to know this, it’s another to experience it for yourself which is the whole point.

Of course, in matters of the heart, it’s hard to say where things will go from there. It isn’t exactly a mathematical equation on what age fits. Sometimes it ends at the first date. Sometimes it never ends at all. But it’s always good to know where you are in the whole thing. It better to be ready if ever that right person comes by rather than being absolutely clueless on what to do. It’s better to make those crucial mistakes in the beginning than pay for it later on in life.

Who knows. For some guys, we might be the next Mr. Demi Moore anyway. Not a bad payoff if ever she were the right person.

38 thoughts on “On Dating Older Women

  1. Gallivanter: There is always something enticing about them isn’t there?

    ChickyBabe: It never fails. For some reason, older women seem to shape men up in no time. Maybe you should thank her for it. 🙂

  2. Perhaps it has to do with the whole: older woman aren’t really good mothers? Biology and all that jazz. Nothing to do with their actual abilities to be mothers, I mean.

  3. Pat: Older women aren’t good mothers? I kinda lost you there. Could you explain that and how it relates to the entire thing?

    Sharina: And experience builds character. The kind of self composition that men often find attractive. 🙂

  4. You would like my blog if your into older woman
    It’s a cougar blog
    I enjoyed reading this post
    and its so true
    In praise of older women!

  5. Hmm but i thought people always say women mature faster than men, so technically wouldn’t older men feel that these younger men are too childish?

    actually i think if i was old, and some younger man was to go after me, i might go for it (if i am still single), it’s not nice being old, it’s nice to have someone younger to bring out the spirit in you!

    as a guy, do you think it will last? because once you grow old, and you see your woman is so old, and there’re many younger girls out there, wouldn’t you feel tempted?
    actually i think that’s the only down side of dating a younger guy!

  6. Huei: Isn’t that the stereotype I was talking about? You’d expect that to happen because it is in our culture for it to happen. You’d expect younger men not to keep up with older women. You’d expect men to prefer younger women. I don’t want to get into the looks matter debate, but there are plenty of older women there that can give their younger counterparts run for their money. I guess I see things in a different perspective because I have dated older women before. That experience makes a difference.

  7. Ed, I meant that biologically, the older you are, the more difficult it is to have children (not counting all the fertility treatments we have today).

    And no, I’m not being discriminative or anything. Just pointing it out.

  8. Pat: That depends solely on the age of the woman and not the age of the woman’s partner. You could have an older woman with an even older male partner and the same biological problem applies. Though with advances in health this isn’t such a big problem anymore.

    I’m the “older woman” in my relationship – my boyfriend is one and a half years younger than me. I don’t think experience comes into it – he is my first boyfriend, I’m his third girlfriend. Our life experiences are so vastly different that there isn’t really any way to rank them. Some things I’m more mature in, other things he’s more mature in. The age doesn’t really factor into anything; we’re just two individuals making this work.

  9. Ti dear, I meant the woman’s age and the prejudices against a woman being older rather than the man being younger. And yes, I did say that with the technology we have now that doesn’t apply any more, so what’s left to change is people’s mindset about older people dating younger people.

    Also dear, my current boyfriend is 1 year and about 5 months younger than me. XD

  10. i’ve got date tomoro with 8 years younger BOY. i am 27 years old now and i really liked him from the first moment i saw him. finally asked him out and gonna meet him tomoro. even though i knew he looked younger than me, but didn’t expect him 19 years old!!! he still doesn’t know how old i am.

  11. im 19 and im am in a relationship with a 30 year old woman. i did not intend on dating someone so much older than me but i am really into her. we have been dating for a year and now we live together. everything seems great. i think its partly to do with my maturity but the chemistry is definently there. sometimes though we talk about our experiences and the things we have done and hearing her stories are sometimes intimidating.
    i end up thinking to myself am i ever goin to get to do those things or go to this place and that place if i continue in this relationship. but she’s a good woman and i like where things are so im going to let this take its course and see how things work out.

  12. hey i am in a similiar situation except i dont live with her and i like how everything is moving but it makes things difficult with the age difference.

  13. I might have the record here,, I am going out with a 40 year old woman, she rocks, I’m 23, umm she is damn fine for 40.

  14. Tomorrow I am going on a first date with a woman who is 33, I am 25. I don’t really see it as a problem, she looks gorgeous and seems interesting to me. I dated a 32 year old before, and in my experience they are much less shallow and more mature then younger women. I absolutely can’t date a teenager they drive me crazy I tried a 19 yr old. I feel like an old man watching over a little kid.

  15. im 46 and have been dating a 28 yr old for a few months now, at first i was categorically against even imagining this being more then a fun and exciting game. and now…im afraid im falling for this very handsome, sweet, tender, intelligent guy. he is winning over my heart and i cant do a thing about it! im glad i can read about how you young guys feel about all this and how other women like me are dealing with the situation. hell! i think im in love and it makes me kinda nervous to say so (says BECK)

  16. I’m 41 have been dating a 33 year old guy. We’ve met online then after few phone calls and emails he decided to come over to met me. We both didnt talk about our age in anyways. I discovered he is 8 years younger than me when we both decided to get a Visa to travel together. He never ask about how old i was because physically, he looks older than me and on the contrary i look more younger than him. We both like same things in many ways shared lots of ups and downs in life, most inportanly we both shared the same faith and religion. We both feel in love and looking forward to be together in marriage. Will update you all soon!

  17. I am currently dating an 18 year old and I am 30. I never thought in a million years I would even consider it. Although, he is a litte “wet between the ears”, our relationship is thriving. I am teaching him a lot about relationships with women he knew nothing of. We are living together and although at times it can be challenging, I am glad that I at least have given him the chance!

  18. Hey i jus joined the dating older women thing. I jus started dating a 20 year old. And I’m 17, not a huge difference like some ive seen here. Anyway, this is legal right. Im turning 18 in 5 months. Is everything legal here? just wondering, please answer, thanks in advance. I live in MD, she lives in VA, I go to to University of Maryland and she goes to Virginia Tech.

  19. This reminds me of a saying I coined many years ago.

    Young woman don’t know what they want. Older woman don’t know what they want either, but they know what they will settle for.

  20. Hi, I am 37 dating a 29 year old man and our chemistry is completely amazing. However, I have been apprehensive about the age difference. Everyone’s opinion has helped. I feel alot better : )

  21. I am a 37 year old woman dating a 21 year old man. I’m also married right now to a 41 year old. I am planning on getting a divorce to be with the younger guy. I may seem unfair and selfish by saying this, but I love the energy the young one has. He has given me life that I’ve been missing for so many years. He enjoys the little things I like and loves to clean! I’m a workaholic and my husband now is fighting for disability due to numerous reasons. He has no energy or will to do anything but play video games and sleep. This is not the kind of marriage I expected although we did not expect his health to deteriorate neither. In all fairness, we were in the swingers lifestyle and that’s how I met my new love. He appreciates everything about me and compliments me all the time on how great and sexy I look. Something I’ve been missing for a long time!

  22. my georgeous lady is 10 yrs older.luv her 2 bits,hav kids and banished from lovin since age of 23. still a kid, this a long time

  23. asked her 2 marry me recently. said no, any advice off females would be appreciated.

  24. I am a 45 year old women who am often told I look like I am in my early to mid thirties, who is embarking on a relationship with a very sexy 20 year old male. I have known this young man since he was 14 and found him attractive then. We are actually quite good friends and he often comes to me for advice on several things. Anyways, I have always wanted to have some kind of fling with this young man and just recently started flirting with him and much to my surprise he was flirting right back. As it turns out he to is very much interested in having a sexual experience with me. Neither one of us is looking at this as any long term type of thing, I think for him it is more a curosity and for myself perhaps I just want to be reminded that I am sexy even though I am 45. Does anyone think that going ahead with our special date in 2 days is wrong?

  25. working again.

    I am in an age gap relationship as well as the older female partner by 10 years. We do not have a problem being in similar place in life and me not having any children or bothersome ex-husband to deal with and the same applies to him. Both of us experienced our youths in basically the same era, so we enjoy the same music and pursued similar endeavors as children.

    We look about approximately the same age, so we don’t get weird stares. The weird stares we have received have been because we are an interracial couple. I think a 15, 20 or more years age difference might present a problem. For me personally my partner is at the upper threshold age-wise for who I would consider dating. My parents were 15 and 19 years older than me, so dating someone that much older would seem incestuous somehow at this point in my life. I feel that we would have less in common. But I can never say never because there’s no guarantee that love will come to you in the socially accepted package.

    Thankfully for us women, the age-gap relationship is becoming more acceptable. The biggest obstacle is when the young man wants children and you can no longer conceive, or when is family and/or friends object. Great social pressure can be brought to bear and many buckle under. I’m not sure why society objects so vehemently to older woman/younger man pairings. And as far as what some mentioned, younger man leaving older woman for hot young female. That can happen to an older woman no matter what age her partner may be. Older men are famous for leaving their wives of the same age for the proverbial 23-year-old secretary. So don’t let that be an excuse for avoiding a younger male, ladies!

  26. Hello,
    Reading encouraged me for writing also here. I am looking for making touch with 45 year old lady, she is neighbours. I want to go with her as much is O>K>, not more. She is not showing me too much but no problem with mouth for her with me. So I also look only for this and maybe when I am having the chance she will take me in her mouth maybe in the car, garage, or behind house. It is okay. I think fun for also her. But I know she will not do this for ever. So I am ready for bye. Ok thanks

  27. I’m a 31 year old guy who knew this women for about 6 months and for the last few months have been dating her. She is almost 42. It’s going well at the moment, but a couple of friends/family do raise an eyebrow and try subtly hinting I ‘should’ be dating women more my age.

  28. Hi everybody
    I am a 23 year old guy who is dating a 43 year old women. She is married (about to get divorced) and she has a 4 kids. I have never dated an older woman and so far I like it. I mean its nothing serious, we meet 2-3 times a week and stuff but she is bothered with the fact that her oldest daughter is older then me.
    What should I say to that?
    This women doesn not look 43, she looks 28 or so.

  29. i will like to meet a divorce woman from anywhere in united state,she must be caring and understand,am just 21 and i live and work in florida

  30. Look you guys I think I got you all beat! I am a 28 year old black man dating a 46 year old white woman and we love each other to death! Age does not matter because age is only the time you have been on the earth! You real age comed from your maturity level! I am a very muture young man and she is mature but upbeat for a 46 year old! She looks maybe 30 years old and has a daughter that is older than me but her family excepts me because i keep her happy and I know how to treat her! Guys out there i wanna tell you that older women are more experienced int their love life and believe me when I say that a older woman will blow your socks off! They have high sex drives just like younger men do! If you know what to do for her then you will bring her inhibitions out really and the chemistry falls into place after that! Older women try it and younger men try it to! As long as you guys are happy then screw everybody else!

  31. Look you guys I think I got you all beat! I am a 28 year old black man dating a 46 year old white woman and we love each other to death! Age does not matter because age is only the time you have been on the earth! You real age comed from your maturity level! I am a very muture young man and she is mature but upbeat for a 46 year old! She looks maybe 30 years old and has a daughter that is older than me but her family excepts me because i keep her happy and I know how to treat her! Guys out there i wanna tell you that older women are more experienced int their love life and believe me when I say that a older woman will blow your socks off! They have high sex drives just like younger men do! If you know what to do for her then you will bring her inhibitions out really and the chemistry falls into place after that! Older women try it and younger men try it to! As long as you guys are happy then screw everybody else! give it a try

  32. I am a Chinese American. I am costantly hit on by guys as young as 20 years my junior. I am almost 42, but can easily pass 22. Not only do I look young, I live young as well.

    There’s guy who is almost 20 years younger. I am not from China, but this guy is. Although he initiated his interest in me and started calling me, he has been under tremendous of psychological pressure. I like him, too and I hate loosing him.

    I have come to read quite a lof of people in China who are in a wide-age-gap of older-woman-younger-man relationship (10+ years). Many of these people are in great pain of true love. They have done nothing wrong, but it is society that gives them the pressure as if they were doing something immoral… so sad.

  33. “Jon”
    Close to you my friend, im 25 and engaged to a 41 year old gorgeous lady who actually has 3 kids, 2 only 5 and 6 years younger then me – that is a small barrier as id really like a child of my own. She has made it clear no more kids, and i think thats a good thing as im accepting my share of responsibility for the 3 she already has.
    The two elder ones treat me more like a bigger brother, which is fine as they open to me more then they would a parental figure. The young boy took a while to accept me, but i treat him like i would a nephew, so I think itll all work out well.
    Good luck to all out there trying this. I honestly cant say if our relationship would stand the test of time, but as for right now its fantastic.

  34. hi all just thot to leave a comment i am a 26 yr old girl dating a 24yr old man and this has been the most fufilling relationship so far . prior to this relationship i had only been with guys 8-10 yrs older and they just never seem to work out. though alot of people were against my current relationship they have recently come to terms with it seeing that we are both obviously headover heel in love . Age definitely doesnt matter in a relationship its all about how you both connect to one another.
    and also sex is absolutely amazing the best evr for me.

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