Should I Date An Older Man?

Every guy I meet who is within my dating age bracket (27 to 35) isn’t what I am looking for. There are many things other than age that make a difference to a woman—for example, education, health, careers, commitment, chemistry...

I would never think of dating an older man if I were just 18... When we are talking about pairing a man, say, 30 and a girl who's 18, they are an appalling mismatch. What could they possibly have in common?
But when I'm 27, dating a man who is 39 suddenly isn't such a shocking idea. So, over the last month or so... I expanded my dating horizons by going out with a man who was 10 years older than I was. I actually found him more attractive than my previous much younger boyfriends and previous men I dated. And I must say... it was different and refreshing. Age did indeed make a difference.

Alas, after 3 dates, we figured out we weren't for each other. But there was something about him being older that I liked. So I thought, ok.. I'll keep my options wider... to include older men... previously the oldest man I had dated was 33, 5 years older than me, and that was it.
Recently, I just had 2 dates with someone who's 12 years older than me. So far, he's impressed me. Should I be open to dating someone a whole decade (or more) older??? Am I asking for trouble?
So... I've been giving it a lot of thought and here's what I feel:
Why I should Date an Older Man (By the way, older man doesn't mean OLD MAN ok... as in one foot in the grave... I'm no Anna Nicole Smith...)
+ Maturity is certainly the more obvious factors. Younger guys are usually just coming into their own and uncertain about life, despite how much they say they've got it together.
+ Older men can be more experienced in the bedroom. They're less likely to be distracted by other superficialities in life because they've probably already been there and done that, while younger men tend to be hungry to put notches in their belt.
+ They are more stable in terms of career and finances. Thus more ready to settle down. (As oppossed to the man who can barely pay his phone bill...)
+ If he's older and more experienced, he can share his wisdom and advice.
+ I don't have to worry about him leaving me for a younger woman. I am the younger woman! (I jest)

Why I shouldn't date an Older Man

-Disaproval from public... Would I be pegged as some kind of gold-digger? Older women will make me public enemy number 1. I wouldn't blame them. If I were single and 38, I might be mean to a young woman stealing from my dating pool.

- I'll be missing out on being with someone who is in the same phase of life as I am; someone with whom I can share the joys and pitfalls of discovery. I want someone to grow old with together, not a decade ahead of me.
- I worry that when I'm 40, all my friends will have young husbands and I'll have an old man. Will I regret that? Or will none of this matter?

- I don't want the risk of having my husband to die ten years before I do. OK.. I know this may sound like an immature even morbid thought. But honestly, one of my greater fears in life is having to grow old alone.

When it comes to dating older men, I feel the pros outweigh the cons. However; the question remains...
How old might be "too old" ???


  1. I will go for it.

    I prefer mature men.

  2. I used to date a man 9 years older than me but gave up due to generation gap.

    If there's no generation gap between the both of you, go for him!

  3. thnx girls for you advice.

    am still wondering is 12 years is a bit too much though...

  4. I'm a 34yr old guy... and from my own experience, there exists a "generation gap" found dating gals below 28yrs old. Maybe it's the 70s kid versus the 80s kid generation.

    Strangely, most of my previous relationships were with 4 years my junior as I found we communicated more or less on the same wavelength.

  5. This comment has been removed by the author.

  6. Have you considered the Freudian implications of wanting to date older men?

    Or maybe on a second thought, you are better off not going there.

  7. Yeah.. better not go there.


    but in my defense, these men.. remind me nothing of my father... in terms of character and looks. So I'm safe right??? I'm not secretly trying to marry my own father am I ??? *gulp* hahaha :)

  8. My father was 11 yrs older than my mother.

    One of my buddy father was 10yrs older than his mother.

    However I can see mother is very faithful as though the husband is able to provide the thing they need.

    A true love happen at the right time in the right situation. If you think that the guy even he 10 yrs older than you. Go for it before regretting losing a Mr Right.


  9. 2nd hamsterlord...

    you said "My father was 11 yrs older than my mother. " did u accidentally use the past tense? or is your father no longer around? Sorry, I have to ask.

    Thank you for sharing... I'm very encouraged to hear of other happy unions between younger women and older men.

  10. Anonymous5:48 pm

    I can't help but notice that you only consider one side of the compatibility question.. ie, do older guys have something to offer you?

    Have you considered whether you have enough to offer them? Especially since you say you're currently aiming for western guys - most of whom are across here with their demanding jobs & varied lifestyles.

    You're a not-well-travelled 27 year old who doesn't have a job, is mad about puppies, collects hello kitty gear, and loves the colour pink. From what I can tell, you're still doing a fair bit of growing up. There is nothing wrong with this, but be realistic. I've been reading this blog for a while now, and question whether you could keep the typical 27 year old westerner mentally stimulated. Let alone someone ten years older still.

    Think about it. The average 37 year old western male in Singapore has probably reached Director grade in, say, finance, has numerous demands on his time, and expects an awful lot from those around him.

    Sure, you're looks will get you a first date. But you're setting yourself up for failure. It's not going to work.

    In my opinion, you've got to start being more realistic. You're dating patterns are erratic, and despite your hyper-self analysis, and top-ten-list-diarrhea, you're still making elementary dating mistakes (taking your puppy on a first date.. are you totally out of your mind..?)

    Take a dating break. Take time out for a month. Stop focusing on the guy, and think about what you're doing, and what you're offering. Then return to the dating scene with a clear idea of what your agenda is.

    Maybe you're more Singaporean than you think. Local guys of a similar age may be a better match than you currently presume. You may think you're more mature than them, but is that really true?

    Sorry for the criticism - just an alternative view.

  11. Why.. thank you anonymous for you lengthy comment.

    You seem to know me very very well. You know that I am immature (based on hello kitty, pink and puppies) and that I am not well travelled (based on thin air), and that I'm somewhat dim and can probably only manage to stimulate the mind of say perhaps a 12 year old.

    I do resent however, that you seem to put forth that I'm some useless bum... because all you know about me is through my blog.

    I'll have you know that, I planned my finances so that I can enjoy at least a comfortable year without working. That is a treat to myself, which I planned for long ago. But even so, with so much time on my hands, I've started teaching English part time, to a deserving bunch of adults, at a private centre.So I still have the freedom and flexibility to live my life however I want.

    Be careful of the opinions you air (anonymous or otherwise)... because you don't know the whole story.

    By the way.. I just got back from the third date with him, so I don't think bringing my puppy crippled my chances very much. Stop being anal about such frivolities.

  12. Anonymous10:55 pm

    Clearly 5:48pm is a local chap, once again aggrieved that a smart, sexy Singaporean girl would prefer to date ang moh men. A word of advice - your asinine analysis and advice based on the random scanning of Holly's blog isn't going to win her over. Holly knows what she wants, and will eventually find it. It just may take her a while. And honestly, if you don't like her "hyper self-analysis and top-ten-list-diarrhea" then there are millions of other blogs out there you can read.

    And incidentally, there's nothing wrong with Hello Kitty. There is, however, something heinously wrong with grown men putting Transformer transfers on their cars. What is with the "men" in this country? Ah yes, their "hyper-maturity", right?

    Lastly, bringing Cookie on a date did Holly no damage whatsoever...

  13. Anonymous11:41 am

    Damn anonymous - you sound like one bitter dude/chick - whichever you are. Seriously man, what makes you an expert on dating advice? I am willing to bet that you are actually single - which deems that your relationship advice would probably be without much merit and more having to do with lashing out.
    I'll give you the skinny - I am 34 years old, higher then a Director level and doing very well for myself, extremely well traveled as well (over 30 countries) and pretty mature on the important facets of my life. I think Holly is an amazing person! What I am not is anal though.
    Sure Holly likes Hello Kitty and pink (seriously Holly as long as you don't get a Hello Kitty tattoo, we're cool :), however that does not by any means define her maturity level. Men globally act like buffoons everytime they watch sports - whether they are 25 or 50 - so does this make them all immature?
    Holly is gorgeous - no doubts about that - but try talking to her for more then 5 minutes and you'll realize that she has an even prettier mind to go with the looks. Just because she knows what she wants and has passion (for blogging and her dog) does not mean that she has erratic dating patterns. I respect that - I respect someone that can be honest about what is important to them and are not afraid to show their true form as opposed to putting on a facade.
    You Mr. Anonymous, are probably projecting some bitter failures of yours or you lack of a dating life or perhaps that you have not found any balance in life yet because you have an artificial standard that nobody can meet (and you think it's because it's their fault probably). Get a life bro - if you find pleasure from readinig Holly's blog and expressing your pathetic and unwarranted opinion about all the wrong things you think she's doing, I would say you need to get a life or get laid real soon dude!


  14. Anonymous1:29 pm

    Sorry that my above point caused so much resentment.

    My point was that, in my opinion, Holly would do well to focus more on why an awful lot of recent dating is quickly breaking down, instead of focusing on changing the segment of men she dates.

    t and 10:55pm are quick to defend, but try dating Holly for a sustained period, as I did, and you may take a different view.

    You may want to dismiss my views as someone ‘projecting some bitter failures’ or someone ‘who can’t get laid’ – thanks for those cheap shots – but I list below some of the points that killed it for me. From reading the blog since, it sounds like it’s killing it for others too. You can, rightly, question what makes me such an expert on dating advice. I’m no expert. And, yes, I should probably stop reading this blog. In fact I'll make this my last comment, come what may. But its annoying to hear Holly’s bewilderment at men cutting off contact or, worse, implying she needs to begin dating more mature guys (which is kinda like suggesting those so far have not been mature enough, which most of the time is not really why they chose to cut off contact… now do you see why it bothered me a little?) Anyway, those points:

    -immediate talk of marriage on first / second date (in the general sense, but still…)
    - call / sms bombardment; no willingness to let the suspense build a little, or just be reasonable on the contact front.
    - little girl tendancies – I personally don’t find hello kitty stuff cute (can you imagine a new yorker doing that for example?)
    - despite an interesting blog, very little interesting conversation on dates – maybe that was just me, but I’ve been told I’m a decent enough conversationist
    - odd habits – taking one’s puppy on a first date is plain weird, whatever anyone says

    P.S. as an ang moh myself, I was trying to suggest that local guys may be a better match, even if they do think Transformer car stickers are cool. And you may find that not all guys act like buffoons every time they watch sports – maybe those that do act over-the-top-stupid whilst watching football are the odd ones out.

  15. Anonymous2:05 pm

    So it was resentment!!! I was spot on - seriously dude, so it did not work out with you and Holly - why are you still so hung up on it? Move on man - sounds like you are digressing on all the reasons things didn't work out and it's obviously bothering you enough to read and reread her blog.
    As for your comment about New Yorkers and Hello Kitty - I live in the US, been here for almost 17 years now and women here do some crazy ass shit. Nobody is perfect in a true sense, they just have to be perfect for one person. If you paid attention to Holly's blog, she does not make any secret of the fact that she is looking to settle, nor does she make any secret of the fact that she does require attention. That's who she is and that's what she wants - all the articulate bullets you listed about things that annoyed you, well there is someone there that will find all those things endearing.
    All I can say is, move on - your comments just make you sound like a bitter ex of Holly. Go find someone that tickles your fancy and let Holly be the way she is because if the way she is is what makes her happy and content then it's really nobody's business to tell her how to live her life!
    Oh one more thing, what is so wrong with bringing a dog - not all first dates have to super formal dude - casual dates make for a relaxing environment - last steady girl I had brought her dog to our first date and that was great, because the dog was a big part of her life and why should she have to hide it.


  16. ok.. anon 5:48pm and 1:29pm.. I think I know who you are, because there was only one guy I had as a boyfriend that I found difficult to have conversation with. (T.V.R am I right?). There was always a formal-ness and I always felt like I was being judged whenever we talked. I remember us painting the room and this is like 2 months into the relationship, and you started conversation with "So what kind of music do the youngsters listen to now?" I was a teacher then. But I remember thinking- what the hell? Maybe you were trying to start the ball rolling, but 2 months into the relationship.. having small talk is just... strange. The guy I am going out with now, mentioned last night that I was a chatterbox... and I actually did think back to the times when I was with you... and though.. now what was wrong with me? Why couldn't I be free and talk to you then?

    But things all happen for a reason. I'm not bitter about the past... you were a complete gentleman and I still remember the look on your face the day I had to walk out of you house that one last time.

    I don't think that the past men I've dated, especially the ones I was dating for some time (like yourself) were immature. Not at all. Ours failed because it wasn't the right time, and we didn't communicate our intentions, and most of all there were just a lot of differences.

    ANd the reason I kep smsing and calling you was because I really liked you and missed you when you weren't with me. It was never meant to be a bid to kill suspense. I'm just like that.

    Don't be bitter or frustrated when you read about my failure at finding the right one... be happy for me because I think I'm almost there now. I'm finally about to get what I want.

  17. I think i'd definitely date a hot 18yr old chick. But probably just for one night...or one night every few weeks..or on weekends after 3am.
    Depends on my mood.

  18. Hey Holly!

    I think age isn't a biggie. The main thing is that the both of you get along and that there's a genuine attraction to each other.

    That said, my experience with this guy 11 years older (you know who la! before my current) wasn't that great. In a nutshell, i felt i was his "trophy girlfriend". On my part, there wasn't strong physical attraction (i'm putting this nicely. heh). It doesn't matter to me that if he ages faster but main thing is that he must be very fit (no paunch!)and healthy - cause that's the lifestyle i embrace and that was lacking in.

    That's my two cents' worth. :)


  19. how old is old.. depends on each other's mentality and whether how well communication goes..

    me seeing someone who is double my age. but due to diff race, believe and age, we missed out alot of topics on purpose. ( would you like that happen to your r'ship?)we even come to a conclusion that we shouldnt continue the relationship because it wouldn't be nice for me and he's afraid I will get hurt later when I lose something more if the r'ship goes further

    there're alot of things you have to think about whether to see a older man or not I think I take it a bit too far off by seeing someone's double my age (that's exactly my parents age), but as long as it's not hurting my own feelings, go on I choose.
    i like ur self-analysis cos u're right somewhere.

    life's too short if you think you wanna go for it, why think so much. =D

  20. Thanks everybody for your comments....


  21. I think there is something about an older guy, BUT saying that it is a case by case situation. I usually only date older guys, i find that for me, it's the maturity and the ability to be independent but still knowing how to treat a girl right!
    and also, girls do mature faster than guys!!

  22. Anonymous12:25 pm

    In actual fact, there's a movie on regarding your "plight" as stated in this post.

    Maybe you should watch it?

    Nevertheless, It's nice though. By Sarah Michelle Geller - SubUrban Girl


  23. I am currently dating a man 14 years my senior. I definitely share alot of similar concerns like you Holly but honestly i would definitely say go for it and at the end of the day age is merely a number. I have made this choice after many bumps along the way and by no means is this an impulsive choice. Will be taking the next step forward and joining him in Europe. Well you know it when u know it ;) Good luck!

  24. Anonymous3:45 am anon 5:48pm is tim, ur ex.....ahahahaha

  25. I believe so... but of course.. not 100% sure

  26. Anonymous9:00 pm

    was intrested -so did you date older guys , what was it like -and wld you recommend ? guy at work ask me for drink but he's like 36 -am 24 -my mother wud freak :- )

  27. hi spice girl... if you are atrtacted to him so far, I recommend goig for tht date. Then you'll find out if you're compatible or not.

    very often.. you'll find (or I have found) that it has nothing really to do with age. compatibility that is.

    I have had younger/same age men with whom I didn't match with. And also older men which were shit as well.

    I'm glad I found one (which seems so far) to be a match. It took me a damn long while to find him. But I feel tht a lot of his maturity and generosity(I dont mean money) has to do with his experience and age. Yet there are other characteristic [ humour, solid chest(haha), intelligence, wit...] which is there regardless of how old he is.. and those characteristics alone would have been enough to attract me.

    I'm rambling aren't I?!

  28. Anonymous3:29 pm

    ... tnx holly , i"m gonna go for drink - see how it goes :-) quite like the idea of having older guy as my b/f !!!

  29. Anonymous2:08 pm

    All but the sex will be an act. A pretense. Especially for a girl so well-advertised -- a fit, opinionated, sex-loving, advice-dispensing Brazilian waxer.

    Remind yourself of that.

    The Mr. Mark fellow seems harmless enough -- but he's intensely sexually satisfied. He can't believe his undeserved luck. Had he met you by an article you'd penned -- without ever seeing a picture of you -- had he met your personality, first, then we could speculate his interest began as more than merely, "I'd like to conquer that."

    Because: you far outshine him.


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