How Come Everyone I Want to Meet Online Isn’t Interested in Me?


I haven’t found a solution for this. How does a 56 year old man find a good younger woman that would be interested in marriage and willing to have children by him? She would need to be 36 to 38. Most good sites line me up with the 50 year olds and most 36 year olds tend to think I’m a dirty old man.   I know that such a person exists but can’t find a good avenue to find her. I am fairly well to do and well educated.


Thank you, Dale, for acknowledging a few very common truths from the world of online dating.

You’re a successful older man who wants to date a woman significantly younger than him.

Websites generally attempt to pair singles with matches who are demographically similar.

Most 36-year-old women think you’re a dirty old man.

Now you’re going to get the same song and dance as every other guy who has written to complain about women on the Internet. I’m going to put you in HER shoes.

So let’s say you’re a 36-year-old woman, entering the prime of your life. You’re done with the bar scene and you’re very much interested in settling down to have a family of your own. How do you set your search criteria? Well, if you’re born in 1971, you’re part of Generation X. You went to high school in the 80’s. Your friends are buying their first houses and having their first kids. You probably want something that looks similar. So you search for men 35-45. Yeah, 45 is a little old, you say, but you want to be open-minded. Maybe he’ll still be vigorous enough to keep up with your active lifestyle.

And then you, the 36-year-old woman, post your profile, and what happens? You get BOMBARDED by emails from fifty and sixty something Baby Boomers looking to trade up in the world. You double check your profile to see if there’s something you wrote that’s attracting these older men. You remove that reference to Steely Dan. You cut how you want to travel in style. Yet these men keep on writing — talking about how they’re young for their age, how they’d love to have children, how they have everything in life except a good younger woman.

If you’re 36, you’re pretty darned confused by these emails. By the time you have your first child, you’ll be 38 or 39. Which will make him, what? 58 or 59? By the time the kid is in high school, Dad will be 74! That’s not the kind of life you imagined for yourself or your children. So you politely decline. Or, to keep things simple, you ignore. And ignore. And ignore. It doesn’t stop older men from writing, but at least you don’t have to explain yourself to a man who doesn’t want to hear your perfectly valid explanation.

Understand, Dale, there is nothing wrong with you being attracted to a fertile and youthful woman in her 30’s. Really. I’m not judging you. But you must understand that any woman you desire online has choices. Lots and lots of choices.

She can go out with a cute, successful man who is 35. Or 40. Or 45. Or 50. Are you getting the idea? This does not mean that you’re not a great guy with a ton to give and the purest intentions. It’s that you’re failing to recognize what most younger women want. A peer. A partner. Not a father figure. You’re still wrapped up in what YOU want.

Needless to say, this goes for ALL people who are dating online. … We want what WE want, even if what we want is unrealistic. We’re all so dazzled by looks and youth that we pass up amazing people who are a much better fit. Who are you going to have more in common with? The woman who graduated high school in the same year as you? Or the woman who could be your daughter?

“I can’t help what I’m attracted to,” say all of my clients — both male and female. And hey, I don’t blame them. I do know, however, that as long as they close their minds to dating people who are age-appropriate, they’re really going to struggle with online dating.

I know you were looking for advice, Dale, so I don’t want to leave you without it. As I see it, you have three options. One, sign up with one of those successful men/younger women sites. At least you know that a woman on MillionaireMatch might be more willing to sacrifice youth for security.

Next, since you can’t convince someone to date an older man, stop trying. To find out who IS interested, try’s Reverse Match. Instead of searching through hundreds of thirtysomething women who wouldn’t give you a second look, Reverse Match shows you who IS open to dating a 56-year-old man. There’ll be fewer numbers, but at least you won’t be wasting your time.

Finally, I implore you to give older women a shot. There are a lot of amazing ones out there and they are criminally underappreciated.

Let’s just hope that they don’t discriminate against men their own age.


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  1. 61

    I once went out with a guy who was 11 years older than me.   I’d never dated anyone that much older before.   But I had a good time – it became obvious to me that he was only interested in using me as arm candy… we actually had a conversation at one point that revealed some of my character and suddenly he got very introspective and rather sad.   He actually teared up a bit because he realized that if he’d met me 11 years prior, he’d have married me and been really happy.
    It made me wonder what he’d been doing all that time… had he been searching for eye candy for 20+ years and then got surprised when I was *more* than something to hang off his arm?   Had he NEVER met any other women like this?   And I knew for sure he was surrounded by amazing women his own age (these kinds of women were the type that mentored me!).
    I guess I’m asking how this guy and maybe “Dale” above got to be 56 or whatever single?   What have they been doing all these years?   And why focus on the young women?   Why not the fabulous women their own age?
    I’m not yet 40 – though I’m getting there – when I do, I’d like to hope/think that I’ll have the opportunity to meet men in my age range still!   If not, I guess I have a little time before I cross the barrier.

  2. 62

    While I agree with many of the points Evan made, I think he’s glossing over one important factor – Dale wants to have kids, which disqualifies women his own age.   Now maybe this is a negotiable item, but I’m assuming it pretty darn important the way it’s worded.   If so, you are far more asking him to settle than compromise.

    Quite frankly, I think Dale should be looking at younger foreign women.   Then generally tend to favor security and family over the more superficial things like looks and “how we will look as a couple” like American women seem to do.

    I have to say, personally I’ve always found online dating to swing in the favor of men more than women.   It always seemed to me women have to humble themselves a little bit and post a profile, where men are used to putting themselves out there.   That insecurity I always found made women more open and a bit less fickle.

  3. 63

    Also, I don’t think it’s unusal at all for an older man to want a younger woman.   Let’s be honest – women tend to have more leverage when they are younger and more beautiful but men tend to as they age and are more sure of themselves and financially secure.  

    @ Ray – we must live in two different world’s hun, b/c 1) I don’t see what you are reporting AT ALL and 2) I think it’s kind of crazy that you would insuiate that women have been held down or kept back in some way when it comes to dating.   The status quo, while changing, has ALWAYS favored women greatly.   I believe that might be personal predjudice talking on your behalf.

    It’s not like he’s looking to date 23 yr old coed bikini models who are full on into the vapid/superficial/party youth phase.   He’s (presumably) talking about mature, adult women.   As you age, the “things in common” gap shrinks.   Mayber it’s taking women longer to grow up these days, I guess….

  4. 64
    Gabe Asher

    @61   I noticed that men will generally date women in their age range up until about 30, then it’s younger from there on out. Women date in their range up until about 22, then look for older dudes UNTIL about 45-50, then they want dudes their own age again. Don’t fight the norm, embrace it and move forward.
    I am on this same program. I am 32, and at this age, women from 17 to 40 are interested in me. I would never choose a woman my age as I have many choices for younger women. My friends and I all agree that we would prefer an average looking teenager who is a “5” for example, than a 35 yo who is a 9 or 10. Youth trumps looks for most men, let’s kick the ballistics here. We are programed to be attracted to fertil women and a 30 yo woman has spent 81% of her eggs. (not to scare the 30somethings here). All the Radiesse/perlane/botox injections, fat transfers, lip injections, neck/brow lifts, chin implants in the world will help women look better for their age, not younger. Mother nature has given us men an “age radar” that is much more advanced than any surgeons knife.
    A 19 yo woman didn’t think it was creepy for her to date a 30 yo when SHE was 19. Now that she is 45 and single, it is now “creepy”. It’s really not creepy to most of them.  It’s an easy excuse to hide their jealousy of another  womans youth. I understand that, we  hate to age. But don’t hate young women, you were also young too, and had your time to enjoy your youth. Don’t hate on the younger women, pass them the torch and be happy for them, for they are in their prime.  Stay positive!

  5. 65

    Ray @ 62: “This is just a convenient pick up line for older men wanting some younger tail.”


    Gabe  Asher @ 66: “A 19 yo woman didn’t think it was creepy for her to date a 30 yo when SHE was 19.”

    I was 18 the first time that a 30-something man hit on me. I could not understand why that old man thought I would be interested in him.

  6. 66

    keep in mind that Gabe  prefers insecure women.   He’s already solidified his attraction as being primarly predatory… not relationship oriented.   His input is informative if nothing more than helping women learn the ‘tells’ to help avoid men like him in real life.  

    It is my observation that secure people of all ages generally prefer people their own age.    Sure, there are exceptions…    Those who prefer large age ranges generally have some personality issues (mommy/daddy issues).   Can’t be too concerned with them though.      Just avoid them.  

    The good thing about online dating is that it is easy to see a man’s preferred age range and choose not to contact him or respond if it is something whacked out.  
       Those men aren’t looking for character and compatibility (as Gabe routinely demonstrates).   You don’t want them.


    1. 66.1

      If Gabe and his buds are sniffing in the directions of teen age girls, they may end up on a date with the business end of her daddy’s shot gun.

  7. 67

    [email protected]

    Sorry… it is  time Dale accept  that he is past his prime as a suitable father.    If he really gave a damn about  kids and sincerely wanted to make a difference in a child’s life, he wouldn’t mind adopting or helping a woman he cares about raise the children she already has.   Which  is why  I believe his intentions are not genuine.   He just wants a younger woman and this is the preferred ‘hook’.   More for his ego than starting a family.   Total BS.  

    There are some new studies that show that  older men’s sperm contribute to birth defects.   It’s not just the women who have to worry about their genetic material getting ‘old’.       

  8. 68

    Gabe, just speaking from my own perspective, I was approached by 30-year-old men when I was 18… and approached by a 36-year-old when I was 21. And then by a 42-year-old man when I was 25. And then, by a 50-year-old when I was 29. I told all of them that they were too old for me. (And yes, I found them creepy.)
    All of them were rather miffed when I said they were too old for me, and spent time trying to convince me that they could better understand me than a man my own age, that I was foolish to pass them up, that if men my own age were so great, why was I still single, etc., etc…. it was rather interesting how bothered they were that I said no, and that I specifically cited their age as a reason. Did they expect that I would fall at their feet simply because I was younger? It’s interesting how upset they got… did they buy into the idea so often spread that their dating pools get larger as they get older and that they could get all of the young women they wanted?
    I ended up marrying a man who was 6 years older than me. That was a safe enough age difference for both of us… did he want a somewhat younger woman for fertility reasons? Sure… but someone who could still relate to him when he had a discussion about growing up in the 1980s and going to college in the 1990s.
    And as for fertility, it does decline the older a woman gets, that is certainly true. I also wouldn’t want to be one to wait until I was 40 to start having babies either. But most women in their early 30s don’t have fertility problems either (at least, not looking at all the growing bellies from early 30s women in my women’s volunteer group and from my former co-workers who are about 30-34)… and this something my husband understood when he pursued me… and so far, he’s been proven correct. With 81% of my eggs gone and all.   🙂
    I know you want what you want Gabe, and I’m not here to harangue you over your desires in women. But I’m just going to say that if you’re going to tell women how we supposedly felt about dating older men when we were 19, then it’s better to hear it straight from our mouths… and yes, you can count me as one of those women who thought it was quite creepy and had no hesitation telling those men exactly how I felt about that.

  9. 69

    Well, as for the egg argument, maybe Gabe wants to date even younger “women” for save measure since a woman loses about 70% of her eggs by puberty.

    So if you want to go for the numbers argument, then why not date 12 years olds?   


  10. 70

    Men really are disconnected from reality.   Evan if you haven’t done so already, can you address on your blog why men are so disconnected when it comes to what they want and what they deserve and what’s really available to them?

    As I  read this all  I could do is shake my head.   I’ve been hit up by  plenty of older men online and they really can’t  grasp the concept of why a woman in her 30’s would not be attracted to a man in his  50’s or 60’s, as if it’s so foreign.        

    1. 70.1

      Most older men were exposed to stories for years about how hard it was for women in their 40s and older to marry or remarry, how older men were much more likely to marry or remarry, how men could marry significantly younger women, and women were happy to trade in their youth for financial security. Most of these studies relied heavily on census data from the 1980s. Today’s landscape has changed   and recent studies reflect that. A man’s odds of marrying a woman 10+ years younger are about 5%.
      A man’s odds of remarrying if he is 45+ are about 30%.   About the same percentage of women 45+ remarry, but women are generally the ones who initiated the divorce and recent studies show they are less inclined to want to remarry.   Some older men don’t understand that women are more independent and have more options. An AARP study from 2003 showed 1/3 of women in their 50s surveyed were in relationships with men 5-10 yrs younger. They probably see Hollywood movies where every aging actor is paired with a woman half his age who wouldn’t give them the time of day in the real world. My guess is when their fantasy doesn’t   happen in the real world, they turn to dating sites.

  11. 71

    Ren #72:
    I am a guy in my late 30’s–successful, well-educated, never married, no kids. I get my share of emails from women who have young kids, are “separated”, and many of these women aren’t that pretty and have a low income. Now, really. WHY would be even remotely interested in dating someone with all that baggage? Did these women stop to think about all this before they took the time to write me?
    Now, do these emails mean that women are disconnected from reality though?
    Now in real life, there are men in their 50’s dating women in their 30’s. It’s not a crazy pairing. Many older men appreciate a younger woman’s physical vitality, and many younger women appreciate an older guy’s experience and wisdom. I doagree with you that online isn’t the place to make something like that happen.

  12. 72
    Katarina Phang

    Gabe #66, speak for yourself.   There’s no doubt that many guys have “fetish” for much younger gals simply because of the age factor and nothing more.   But there are many guys who are very attracted to much older attractive women too (or women their age).

    If porn is any indication, how much MILF genre lovers out there?   And how much hotter these women are compared to a 20’s?  

    It’s mostly not about age but how one takes care of him/herself.   I still got hit by much younger guys on a daily basis in my 40’s now.   And I can be attracted to a 56 yo if he takes good care of himself (though whether or not we are compatible in other ways is another story).

    I agree with Ren, men who think it’s a given that much younger women will be attracted to them on the virtue of their “wisdom and experience” are delusional. Not every middle-aged guy has George Clooney charm.   Most are sloppy looking.

    But the younger a woman is the more sensitive she is to an “old age” appearance.   When I was 25, most 35-40 old guys sounded (and perhaps looked) so old, too old for my liking.   I couldn’t date a guy who was close to my dad in terms of age and appearance (and my dad is only 21 years older than me).

    These days I have far more tolerance about wrinkles/older look appearance but it’s only because I have grown so much and know looks are only a small part that makes relationship work even if it’s still very important.   I won’t be attracted to most 30’s, 40’s or 50’s (or even 20’s) guys but it’s not because of their age but because I don’t feel physical attraction.   

  13. 73
    Katarina Phang

    I have a decent looking Asian male friend in his late 30’s who thinks that a 25 yo is an ideal future wife for him.   Problem is 25 yo women aren’t interested in him and even if they are the chance for the relationship to work is perhaps slim to none.

    I kept telling him to find a woman in her 30’s (or in his own age range).   He’s still looking -and is still drawn to women in their early to mid 20’s- and keeps complaining how lonely he is.

  14. 74
    so very true

    it is the women that are just too picky today, when it comes to men. they are waiting for a prince on a white horse to come and sweep them off their feet. what a case. it is bad enough that women today are so very nasty, with their rotten no good attitude problem which makes it worse. this is the absolute reason, why us straight men are having a difficult time meeting a good woman today. cannot blame ourselves, since they changed so very badly today.

    1. 74.1

      Women are picky? Lmao.. every man alive thinks he deserves a ten,that’s why men like you are gonna be single forever.But women aren’t real people who should have choices of their own eh sport?.What do YOU have to offer a good woman?.You never think about that do you, it’s all about what YOU think you deserve.

  15. 75

    One time I was at one of my local hangout patio bars where 20-30 something professionals and students hang out. These two old men had to be in their late 70’s. This was about 5 years ago, I had to be about 27 I am 31 now. My friend who was with me was 22, and her guy friend was about 26. These two old men who were probably in their mid to late 70’s were hanging out in the bar. I remember thinking to myself, “ew they are older than my dad and they are hanging out in here?” I went to the bar to get a drink, and they offered to buy me a drink. I politely decline and said I would get own. I got my beer and walked away to sit with my friends. About two minutes later, I felt strange hands on my shoulders and turned around and literally freaked out and yelled “don’t f**king touch me!” I scared them so bad they left the bar immediately. I think I even spouted out “go home to your wives jeez!”
    I agree that it comes across as pedophilia to me. I mean how young did they like them when they were my age? Were they creeping around the high schools? Junior high? I mean really?!
    Lately I have been hit on younger men, anywhere from 24 to 27. But even 24 is only 7 years age difference. I agree that around 24 or 25 there isn’t too much to talk about for too long because of a maturity gap, but I have gone out with someone 4 years younger than me. At 31, 27 or 28 year old men are pretty much on the same level as I am. There isn’t much of a difference. Even 25 I would give a chance to. We still like to do the same things, and can find common interests. I am not the “older woman”. So even though the men are younger, yeah I would say that I still have enough in common.
    But what on earth makes grandpa think that women of “daughter’s age” want to sleep with their fathers? Give it up Dale, and figure out what it is you missed in your youth that is causing you to be attracted to women that young. You might need some therapy and work some issues out, and that desire will fade away once you can connect with someone from your own generation.

  16. 76

    I’m 44 and only date women in their 20s.   It’s easy.   How do I do it?   Stay OFF THE INTERNET DATING sites.   Meet people in real life.   The same girls who would brush me off as a creep on OKCupid think absolutely nothing of the age difference when they meet me in real life and see how interesting and vital I am.   26 year old girls hop in my bed ALL THE TIME and half of them fall totally in love with me.

    1. 76.1

      So you enjoy making multiple young women “fall in love with you” and presumably want you to be exclusive with them, or marry them, even though you’re not interested in that.   That’s just sad.

  17. 77

    Fascinating topic. I have a friend who is dating a woman 20 years younger than him (shes 23), another dating a girl 13 years younger (shes 30) and i recently dated a man 13 years older than me. Another friend has been with her man for 10 years and he’s 17 years younger than her (he was 23 when they met you do the math). Are any less feasible than the others? i don’t think so, is long as everyone is on the same page. And although Michaels comment is just CREEPY, he’s right, by meeting in real life you get a better view of the whole person than a dating site.
    My question is though, if the SAME GIRLS would brush him off as a creep on a site, why on earth are they ok with dating someone with that age gap in real life? sounds to me like they are oncers.otherwise he would be in a relationship by now.

  18. 78

    this is so true, and it makes me mad! i am 30, and i look REALLY young for my age (some people think i’m still in high school). and i get messages from men in their 50s and 60s. (the oldest so far was 69). it’s gross! most of these guys are older than my dad! and then the guys my own age want 18-year olds! seriously guys dream on…grow up and get your priorities straight!

  19. 79

    @ Mavis

    “this is so true, and it makes me mad! i am 30, and i look REALLY young for my age (some people think i’m still in high
    school). and i get messages from men in their 50s and 60s. (the oldest so far was 69). it’s gross! most of these guys are
    older than my dad!”

    Older guys are generally clueless about the expectations of (in particular younger) women.

    “and then the guys my own age want 18-year olds! seriously guys dream on…grow up and get your priorities straight!”

    I’m in my late 30’s and when I was looking for local women, I found I simply couldn’t connect with women close to my
    age, despite repeated attempts.

    I got the distinct vibe that they were so emotionally damaged from years of abusive partners, and repeated
    rounds of pump-and-dumps, that their toxic expectations were palpable(ie. they were now resolved to snaring a hunk
    with money, so that *when* he cheats they could reap financial gain for themselves and their brood of illegitimate

    I observed that this sample was characteristically aloof, defensive, vulgar, flaky, and frequently uncommunicative.

    In fact, the women who I initially connected with were 18 and 19 year olds, who fell in love me with on sight(I am also
    ‘cursed’ by looking like an 18 year old – and at the time, I looked like a goth rockstar, lol).

    It was pure infatuation on their part, but I would be lying to say that I didn’t find them more agreeable company – they were relatively inexperienced(much like myself – I was a *very* late bloomer, and had no relationship history to speak of), and idealistic in their expectations.

    Their naivety was very refreshing, and I came to appreciate that despite the chronological gulf between us, I shared much more in common with young women, than my age peers.

    Alas, I was not comfortable with such an extreme age gap, but when I reflect back on my experiences, I have to say that I was never able to establish a connection with any woman older than her mid-twenties(which is what I ‘settled’ on).

    So, yeah, it isn’t as far-fetched as you might think(and unlike with the whole cougar dynamic, there is no reason to suspect that older male/younger female pairings are a function of older men being ‘easier’, lol).

    Also, we have to remember that full male expression of secondary sexual characteristics occur over a greater span of their life history, while neoteny is an important factor in the expression of female characteristics(explaining a singular bias for young females in mate selection).

    But, I confess to (intially)being somewhat perplexed that lower value women(older, less physically
    attractive women in their 30’s *with* children), could presume to be *more* selective(or less receptive), than higher value women(ie. younger and more beautiful).

    So, to any such women who are still struggling to find the ‘one’, I can only say it does not hold that being more selective, at a lower level of attractiveness in advancing age, will meet with greater success(than the past).

    1. 79.1

      I wholeheartedly disagree with your assertion that, as a 32 year old woman, i automatically have less value and am less attractive now than when I was younger. I look at other women online all the time, and I have to say, I am much better looking than the younger, chubbier women who run rampant on these sites. Who says that just because a woman is past 30, she’s somehow passed her expiration date. I am way better as a partner and as a woman (not a girl, a woman) than I was even a few years ago. You know what I think the problem most men have is? They know that a woman their own age likely will not put up with their bullshit. No wonder so many older guys like females who are young enough to be their daughters – they’re the only ones left. They don’t know any better!

  20. 80

    If older men continuously try and message me even after they see my preferred age range, they are going to get used. Simple as that. But, in the end, they want to be used. Why else would a 59 year old man message a 22 year old girl? He has nothing to offer but money. And that’s what she’ll take him for.

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