Why Would a Younger Woman Want to Date a Much Older Man?

Okay, Evan, I agree mostly with your opinion on younger men/older women. What do you say about the reverse? I mean, I can see why an older man would want to date a younger woman – physically that is, but why would a 28-year-old woman want to date a man 45 or more?


Dear Penelope,

Beats the shit out of me.

I can totally understand why older men go for younger women. There’s no denying that they’re, for the most part, in better shape, with better skin, and less baggage from broken relationships. Time creates wisdom – but it also creates responsibilities and complications – mortgage, kids, career, etc. All of this makes dating more and more complex as we get older. It’s a lot easier for a man to take out a carefree, responsibility free, baggage free, wrinkle free 28-year-old, which is why so many men try to go in that direction. I’m not condoning this. I’m OBSERVING that it happens.

Still, most of them fail miserably, for the exact same reasons that I think Penelope is suggesting. Men want much younger women, but rarely do much younger women want older men. Put another way, if a woman has an array of other quality options closer to her age range, what incentives would she have to date a man who is SEVENTEEN YEARS OLDER?

She doesn’t NEED a guy who’s 45. She can find that same amazing guy at age 30. Or 35. Or 40.

Not many, I’m thinking.

Before any 40+ people get all hot and bothered about this – I am not judging. There is nothing wrong with aging. I do think people improve with age (my wife is nodding). But let’s not pretend that we, as a culture, don’t worship at the altar of youth. If you’re over the age of 40 and have ever said, “But I’m told I look five years younger than my age”, then you’re not immune to it yourself. But see, for men who covet younger women, it’s not whether you look good for your age – it’s what age you really are.

Because it’s competitive out there for all of us. People have choices. And nobody has more choices than a 28-year-old woman. If she wants to date a guy who is 6’2”, makes $400,000+, likes skiing, is within ten miles of her house and five years of her age, you know what? She could probably find him. All she has to do is go on Match.com, and wade through a few thousand applicants. The point is, she doesn’t NEED a guy who’s 45. She can find that same amazing guy at age 30. Or 35. Or 40. She doesn’t need a guy who will be taking Viagra when she’s sexually peaking at 43.

Don’t get me wrong, there are advantages in a 45-year-old guy. He’s probably a man. He’s got the job and the home and the car, and been divorced with a kid already. So if a woman finds it more appealing to just step into that world – to jump from the prolonged adolescence of the late 20’s into full-fledged settled-down womanhood – that could make sense.

Most of them are completely creeped out at the prospect of dating a guy who was alive when JFK was alive.

There are many other things that are attractive about older men. They embody wisdom and stability. They can afford nicer restaurants and vacations and have cultivated greater tastes in the arts. They’re more experienced, more chivalrous, and more likely to want to settle down than a twentysomething party boy.

And yet, they probably resemble Penelope’s dad more than they resemble her brother….

This is the most compelling reason behind why younger women might go for older men: they’re daddy substitutes. An older man’s going to be the strong, nurturing guy who takes care of her, teaches her, and treats her like a princess – the kind of relationship that she probably lacked growing up.

Hey, I’m no psychologist – just your friendly, neighborhood dating coach. But I do know women, and lots of women in their 20’s. And the truth is that most of them are completely creeped out at the prospect of dating a guy who was alive when JFK was alive. These women were born in the EIGHTIES. They grew up with computers. They’re contemporaries with Britney Spears. Whether we like it or not, there is nearly a full generation gap between 28 and 45. A few women may bridge this gap for lust or money or dimestore psychological reasons, but most of the 28-year-old women I know would prefer to date a great, stable 30-40 year-old – who also knows what Snapchat is.

Okay, older men – tell me why I’m wrong. But don’t forget, you and your younger girlfriends are the EXCEPTION. I’m writing about the RULE.

By the way, my girlfriend wants it on record that she would totally sleep with Harrison Ford if he should be reading this. So as a gift to both of them: Sure, why not? Happy 66th, Indy!

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  1. 541

    Scratching your head as to what young girls see in older guys? Let me tell you, at least from my experience (I am 27, he is 63):

    1) He is mature and responsible

    2) well-mannered; chivalrous; gentleman

    3) similar interests, values, and politics

    4) father figure: teacher, mentor, protector

    5) extremely fit and takes excellent care of his body, so he looks much younger

    6) sweet, kind, and considerate

    7) loyal and trustworthy

    Sure, I could find all these qualities in a younger guy, though less likely. But I didn’t. I found them in him, and he happens to be much older.

  2. 542
    Susan weaver

    I don’t think a man of 65 should be having sex with a girl 25 and having a baby with her .  That is like have sex with your granddaughter.  But the man don’t want his baby to start dating when she is 25 years old but he started to have sex with her mom when she was 23 but I guess it wasn’t his daughter but it was someone else’s daughter.  The man might be physically fit but he did just have surgery and the girl will eventually have to raise the baby herself oh and by the way she is slow but when a man that old they think with there little head and not there head that has a brain so i just dont think a man that age should of but it takes 2 to tango

  3. 543

    Last summer I met a girl at work who was 27. I was 51. After working together for a year, she text’d me one Saturday night. At first I didn’t think much about the prospect of dating her. But after a she started persueing me, we went out a few times, we really hit it off. There were many nights we would talk on the phone laughing until early morning. She still didn’t know how old I was at this point.

    One day she just straight up asked me how old I was. When I told her, she got very quiet… for days she didn’t reply or reach out. As it turns out, she was contemplating how to get out of the relationship she had started with me. So she sabotaged us by jumping in the backseat of my truck and taking off her clothes… only to stop and blame me for not stopping her. Easy out! Right?

    Anyway, when it all calmed down, she admitted the she felt the age difference was just too great.

  4. 544

    My sweet spot is men who are 10 years older. It feels like those men are less likely to play games, cheat on me, and leave me for a younger woman. They already made most of their mistakes, and learned most of their lessons with other women when they were younger. They’re more likely to get serious, and that’s what I want. I don’t want to move too slowly, that doesn’t mean I want to rush things either. I also feel incredibly young and beautiful next to him, and I don’t feel like I have to compete with other beautiful young women and have to measure up and stay current with them. Airbrush my instagram photos, and count my likes and stuff.Being with an older man makes me feel like a prize, and like I can be rest assured that he’s going to hold onto the prize, and not take it for granted. If I date a man my exact age, even just six months older, it makes me feel like an old lady. But, that’s probably because I have a lot of life experience, more so than the average man or woman. My experience of dating a men my own age is that they’re annoying like a little pup that I want to growl and snap at. I get so annoyed with their wet-behind-the-ears-ness. It’s just not sexy to feel like you have more life experience than your man.But… I’ll not go over 13 year older.  I’m strongly not attracted to men who are 20 years older than me.. I think about changing their diapers one day and wonder what’s in it for me in the years to come? Aside from maybe being left all his assets once I help him die.

  5. 545

    I have been dating for 7 months a 19 year old and I’m 63 years old. How did that happen? I live healthy and have no bad habits to start with, like drinking and smoking. I go to the gym 4 days a week and I have an interesting job writing and creating jingles for auto commercials. I’m not wealthy but comfortable. I try to dress nice, but my hair I keep short because it’s going bald. I don’t think any of these things really made her accept a first date with me. I think it was humor, being very honest and treating her very special. I told her we both know this isn’t going to work forever, so let’s have some fun and if Mr. Perfect rolls into town, I completely understand. She’s is totally awesome and a beauty. I don’t deserve her in my life. I keep it lite. Fresh and I disappear often not looking needy or controlling. That’s made things smooth. I don’t ask her any questions that might strangle the friendship because in the end I would enjoy being friends. Trusting, being open and understanding the mindset of her age has been key. So far we have taken a short cruise, a few trips to Del Mar California. We go to a rock wall and climb indoors. She smokes me in most athletic situations and I just roll with it. I surprise her with small gifts and plan thing that are hopefully something new she hasn’t tried. She has also bought me a shirt and treated me to a live event. Not a single person has said anything negative about us dating from either side. It’s so fricking strange and unusual but why would I rock the boat. Before this I didn’t date a single person for 17 months.

    1. 545.1
      Yet Another Guy


      If you are looking for validation on this blog, I doubt that you will find it. The age gap and the age of the young lady go beyond qualifying you for creep status.  I look great for my age.  I go to the gym five-plus days a week. That does not mean I should date women half my age, let alone one less than a third my age.  What you are doing not only displays a lack of judgement and maturity, it is predatory behavior.  The young lady was a minor two years ago, and you are old enough to be her grandfather.  What you should have done was tell the young lady that you were flattered, but she is too young for you.  Heck, I do that with thirty-something women, and you have seven years on me.

  6. 546
    Samantha Genni

    I asked my girlfriend who is 25 i am 44 why she would go out with me her answer was simple because she loves me…age is a number…

  7. 547

    I’m 26 with a 48 year old man, he is my soulmate believe it or not but it works. I love that he has his stuff together I don’t have to worry about him out here messing around on me like BOYS my age who normally isn’t a man, doesn’t have his affairs in order, doesn’t know what he wants, and just wants to hop around girl to girl. I love how my older boyfriend nurtures me yes, he makes me feel like a QUEEN not a princess he treats me as his better other half. He works hard and is a very busy man but I am provided for I want for nothing he Is by far more healthier, and has more drive then a 20 year old boy forreal. He teaches me things and I learn from him everyday because he wants to make me a better woman and does a great job at it, he always tells me I’m the best but I can always be better. I love that about him. He listens, he’s romantic, he’s, just the whole package. Another big thing I love is when he comes home from work he don’t go straight to the couch and flips the tv on no he loves on me, asks me about my day then we relax together I never have to beg for his affection. Sorry but I have never seen a man my age know what he needs to do for a woman.

  8. 548

    I’m 31 years and I met someone that is 47 years old at first I was scared about the relationship as I got to know him he’s a wonderful man he treats me well he’s full of knowledge and Im very happy I love him so much and sex is great.

  9. 549

    This seems so true. I am 23 years old and I’m dating a 56 year old. I am scared of letting my family know I am dating a man over 30 years older. I love him so much and he been my best lover, romantic, loyal, passionate understanding and chivalrous. I find it harder dating younger men because I’m in college and it too much energy in dating and fussing with someone close to my age. Most younger men are scared and shy nerds or just bold and immature for me. I have rejected them in most cases out of fear of dealing with drama and uncommittment. Also, my last relationship was a 3 year hurricane with a 26 year old and it was abusive .I let my last relationship almost cost me my life and dreams.   I think what attracts woman to an older man isn’t necessarily his age , but I think it has to do with a woman’s upbringing. I come from a Latin family where my grandpa is 70 and loves and support a woman who is 40 year old. In some countries dating a man with stability regardless of age is acceptable. I also was raised by neglectful parents whom suffered mental and substance abuse. As a result I experienced abuse, and trauma. I never had stability growing up. Also,  being with an older man who has experienced  marriage, having a nuclear household, and healthy relationship has change my dark perception of what and how a relationship should be. Thank you Evan.

  10. 550

    I’m 23 dating a 42-year-old man. Honestly, for us it’s more than just sex, it’s like a connection that neither of us got with anyone our own age. We understand each other on a deeper level, we both pay for stuff (Even though he pulls out his wallet quicker than I can pull my purse out lol.) I don’t want him or anyone else thinking that I want money from him, I get accused of that all the time by people neither of us knows. But it’s not even about that, it’s hard to explain but wisdom, experience, and power is something that I crave which he has. My dad wasn’t in my life, and my stepdad who raised me passed away recently, he’s really helped me through a lot of it. I’m not saying we’re in love, that’s a whole new area that we really haven’t even discussed. But we are there for each other, almost like best friends. But the sex is pretty amazing too lol.

  11. 551
    Kerrie Hurley

    I am 50 years old and have reconnected with my high school US History Teacher, who I had the biggest crust on. He is 78. He is young at heart, healthy, walks, works out, is very together.

    We have fallen madly in love with one another and I don’t see his age at all.

    With that being said, everyone else sees his age and have commented on it. I know this shouldn’t b other me, but sometimes it does. His youngest child said I just wanted him for his money. my child and ex husband say it’s sick!

    I honestly don’t care what anyone says or thinks. I have found happiness with this man, like I have never known. He is kind, sweet, a real gentleman, which is a dying breed. I want to marry him and if I was 30, I would want ten of his babies. Just saying.

    My only fear is him dying. I don’t think I could live without him.

    Girlfriends have said, I could die before him, which is a valid point. No one knows what their fate will be. I just know before this wonderful man came into my life again, I didn’t want or need a man and 78 would have been ancient to me. That is no longer the case. He is the true love of my life.

  12. 552

    I am 54 and in better shape than 90% of the 20 30 40 and 50 year old men on the planet.  I have tried dating women in 60s 50s 40s 30s and 20s.  I have found the 50ish  ladies are like fat old cats and the 20ish ladies are like puppies.  Women in the 30’s are just confused and too stupid to evaluate.   I am currently in a relationship with a 28 yo and it’s working fabulously.  It is problematic that I am closer to her dad and mom’s age.   People do not approve.   We do not care.  It really is working well.   I have been married 2x and have 3 grand children and 3 children all near her age.   She does not want kids.   she has found men her own age and even 10 years older to be immature and she does not like how controlling and what shining little bitches they can be.  She is mostly in it for security, stability and lifestyle.   She has just been out of college and is starting her career.   She loves me, respects me and values me as a mentor and a lover.  I am in it because she is smart, loyal and honest and looks like a model and in fact is a retired model.    She does not say no.  She says I will think about it and yes.   Its working.   Good luck to you all.

    1. 552.1
      Yet Another Guy


      Come back in ten years and tell us how well dating women that much your junior is working for you.  You will be an old man who is headed towards retirement while she will be reaching her prime.  I am a few years your senior, still very muscular, and I have a full head of non-gray, non-colored hair.  I am also not a grandfather.  A 28-year-old women is way too young for to me to seriously consider as a partner.

  13. 553

    I personally don’t think there are any “wrong” answers to this issue.  I’ve kept up with the commentary and I too have a relationship with women much younger than me even tho I am  married.  About 6 years ago (age 64 now) my wife proclaimed she despised sex and why don’t you find someone to help you with that.  Well. They opened the door to what I had never experienced before.  Normal night of intimacy was pre-served by “hurry and finish” or let’s don’t and say we did”. Such great turn ons.  Other than that we are great friends. Have two great children, one grandson and two more innthe way this year.

    So I have met a young lady who we actually care about each other at a high level. Only talked so far and this coming week after two years of discussion decided we would meet.  She is a lot younger than me and while I could enjoy living with her for the time I am active I see that longevity will not be fair to her.  So not sure where we end up but at least for a moment in time we will enjoy our time together. Regarding my wife and family if I got caught I would deserve the heat from the obvious heartache we all would have. But I find many opportunities to enjoy the bliss of a younger woman if I were willing to take advantage of of it.  I’m 64. Not dead sexually. And frankly it’s frustating to say the least. So there you have it.  Not ready to sign of sexually in NC

  14. 554

    In the end people should let people be and date whomever they wish. So much damn judging on this post. If someone wants to date another who is 15, 20, 30 years older or younger, that is their choice. People fall in love based on a variety of factors, and for the most part, age is not one of them. Most do not care, as it should be.

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