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…

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