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

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. 301

    The reason is that nature does not want the young breeding with the old. It’s natural selection.

  2. 302

    Evan is too kind but I’m going to be more blunt with you as I would to a male friend. The honest truth is this ain’t not gonna happen.  If this is your criteria your chances are slim to none of meeting a woman for a solid happy relationship.  Now if you are wealthy you may find some young woman who will use you but that’s not a happy life. I’m 40 and I would not consider dating a man your age.  I don’t know any woman in my social circle that would and I’m by your standards too old.  And having kids? I’m sorry but just because you can reproduce forever does not mean you should.  A 36 year old woman would likely end up parenting your child solo as she will outlive you and  do you know how much work an infant is? And let’s talk about sex . You better stock up on viagra! Oh wait you are one of those guys that is like a 20 year old in bed right?  Because all older men looking for younger women are.  As someone who had had sex with a 20 year old a 30 year old and a 48 year old there’s a difference!  And sorry but I don’t want to deal with ED or having sec once a week or you getting too tired or having back pain. My advice go out and mingle with women your own age and if you have a burning desire to have kids, date women with kids, consider adopting an older child or volunteer to be a mentor.  Or just keep doing what you are doing and be in the same spot in 10 years. Of course everyone has this friend who is your age who tells a story of a friend of a friend who met a woman that was 15 years younger and lived happily ever after.  But it’s a rarity.  One last point. I find an influx of men over 45 who are childless and pushing to have kids. They messed around and did not settle down and now can’t find anyone to bear their children. I think men need to consider this too. We all have a timeline and it  can’t be extended forever!

  3. 303

    Well, I have to say some of the comments from the men on here are laughable, im 53 and I wouldn’t date an older man. You might think youre fit but you really are not! Get real. A younger woman is after your money, live with it and dont come running back when you FINALLY wise up lol.  Women ignore thesr men , theyre no use to anyone

  4. 304

    I am a 36 year old woman (born in 1981 btw not 1971). I have a close male friend in his late 50s, but do not view him in a romantic way. My partner just turned 45, and generally I prefer to date from my age to 50-ish. I don’t think this guy is being realistic. This is not Hollywood; it’s real life. If he wanted kids, then maybe he should have considered settling down earlier. I don’t have or want kids, and neither does my partner, so it’s not an issue for us.

    1. 304.1

      Christ, I didn’t realise this post was 10 years old!

  5. 305

    As a 43 year old woman online dating, I rarely meet men in their 40’s or 50’s who will even take me out on a first date. The odd thing is I have no problem getting dates (multiple) with men in their 30’s. If I dated 20 something men, it would be even easier. Out in the real world? I get hit on ALL THE TIME by men in their 40’s /50’s.

    I think men in their 40’s / 50’s assume that women in their 40’s are past their prime and not fun. A lot assume my pics are fake or photoshopped. I think when they meet me offline, they assume I’m younger (although I know a lot of women my age that look like me- it’s just a matter of caring for yourself.)

    However, if you want a baby, and you are a 56 year old man, a woman my age is a terrible bet. You have to find a younger woman, and in this day and age, smart, attractive younger women have careers, their own money, and a lot of choices. Men in their 30’s are no slouches either. They are vibrant, well mannered, smart, healthy and often wealthy. It’s why I stopped bothering trying with older men- because I can find a 37 year old (often with a child from a previous marriage), who will happily court me.

    At 56, in 9 years you are 65 and your health declines. So your 30 something wife is raising a kid and worrying about your health and a kid under the age of 10. I’m 43…. if at 33, I had dated a 56 year old man, today he’d be 66. At 43, I do things like Crossfit, travel, enjoy great health, hang out with younger and older co-workers. My experience of a 66 year old man is my father- who at 66 retired, and began a rapid health decline. At 67, he had limited mobility. I can’t imagine at 43 being stuck with a man like my father- who couldn’t take a walk with me?

    So… if you are 56 and don’t understand why younger women won’t take you seriously- it’s just a disconnect down the road. It’s the same reason a 29 year old will date me *for now* but won’t get serious- sure, I’m pretty, fun, but when he is 39 and wants kids, I’m 53 and menopaused.

  6. 306

    Get off your ass and go places were singles are, not online. My male roommate converses with women online and it’s pitiful.  To get a good relationship it’s important to look the person in the eye. Can you do that online, no!

  7. 307

    I just spent over 1 hour reading most of these posts. Sigh. Realistically most woman would like to be with a guy her age or 5 years younger. Women are making more money we have more options. 10 years from now will it be a big deal for women to date younger men… No. But the older guys hate this because they have lesser value. I mean for men to say they have to go to another country to get younger women…. Need we say more? I dated a younger man by 9 years and he married someone his age. I was surprise how he let himself go and sadly he looks older than me.  Anyway to each it’s own but if you ask any woman who is making good money… She wants someone her age or younger. Women live longer. And for the older men…. Breathe and let it go. Hollywood movies are just that. Go for the woman that gives you 80 percent not someone who will just give 20 percent. Oh and a lot of single dads late 20’s and early 30’s have wanted to date me but I am realistic to understand that over 8 years younger…. Trouble. And most men know that a woman 8 years younger not happening as much as they wish or want because women are making more money. Once again women want their age or 5 years younger. Much respect. Honesty.

  8. 308
    a healthcare worker

    In general it’s not a good idea to date someone much older than you, whether that be male or female. Many people get diseases that they have to have lifestyle restrictions for, and those that don’t follow those restrictions can get some serious damage to their bodies sooner than later. This means that eventually you’re looking at taking care of the persons daily activities of life such as cleaning them feeding them or bathing them, helping them poop, taking them to the hospital. For normal people to make such a committed effort to take care of that person, they need a long term investment in the person ie that person is their family, parents child spouse. So if you date someone a lot younger than you, there’s a chance you won’t get the care you need, from someone that actually cares about you. You’re really better off dating and marrying someone around your own age, because when that time comes when you need someone to take care of you, roll you to make sure you don’t get wounds, change your urine catheter or give you daily feeding or give you medications, you want to make sure that they have the loyalty and commitment to be willing to sacrifice their freedom and happiness for you. So if you only care about the superficial, then that will be the foundation for them to run when things get rocky.

  9. 309

    I am 61 and like younger women for one thing………

    ……..they are simply nicer human beings !


    Older women who are not in a loving relationship

    get bitchy and mean…………

    single women in their 20’s are far more pleasant

    1. 309.1

      that’s cuz men haven’t ruined them yet. “older women who are not in a loving relationship” – that sounds again like the man’s fault.

  10. 310

    As a millennial, I have no desire to be with an older man. They gross me out in ways that are unimaginable. I don’t care how rich you are, my skin crawls when old men look at me.

    Why would I choose you when men my own age are better looking, less condescending and more fun? I want someone to experience life with, and if you’ve already been there and done that, there’s nothing to experience together.

    Why are you guys so creepy? Leaving wives who’ve bent over backward for you, built a life with you, just because you think you deserve a younger model? Get over yourselves.

  11. 311
    Gundu Reddy

    There are a few women who genuinely like older men , just like there are a few men who genuinely like much older women. You have to use sites like reverse match and find people who are specifically looking for an older man to have children with . The more specific you are , the less matches but the less likely you are to waste your time . There also has to be incentive to choose an older father for her children . If you make it clear that your future partner would not have to work , would be supported financially , and would be provided a certain lifestyle your chances will increase dramatically . However you will not attract the type of women whom you used to date in your thirties . Going younger is a compromise for men , just as going older is often a comprimise for women. You have to be certain of what type of compromises you are willing to make .

  12. 312

    Apparently, this site attracts a lot of 50-somethings who look 10 to 15 years younger. Why don’t you all stop bickering and ask each other out? Isn’t that what you want? Someone your own age but all the youth and vitality you claim to possess? Aren’t you so thankful and grateful to find this site of like-minded singles! Go on people, start trading email addresses!

    My experience with on-line dating shows me that men my age look really rough! They start looking really bad at the 9s – 29, 39 and 49. Hmmm…either there’s a disproportionate amount of rough-looking dudes at age “cusps” or gasp, could they be lying about their age? Especially to get the coveted “2” or “3” or “4” in front of their age number to miss those pesty age range cutoffs, such as 30-49. Just like in real estate, people don’t usually list their property at say 250K, it’s usually 249K, to reach a broader pool of buyers.

    So the reason many of you look around and say “Gee, all the people my age look terrible” may simply be because they aren’t your age. They are lying. Then you go and lie about your age because you think you look better than your contemporaries, thus perpetuating the cycle.

    Really people, stop lying about your age!

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