22-year-old man: “How to approach older women?”

Jan. 23, 2016 update: I’m getting so many questions on this subject. I get emails from younger men — mostly age 18 to 30ish — who are attracted to older women (usually 60+). So I’m resurrecting this earlier post and inviting comments from both young men about what attracts them to older women and from older women about how a younger man can find them and make contact. Are any of the online dating sites especially good to help younger/older connect?

Note: I am NOT matchmaking here, though many young men have begged me to post their email addresses or phone numbers. No, I won’t do that. And guys, please don’t ask me personally to hook up with you! That kind of request — yes, I do get them — feels creepy, and I won’t even answer to tell you to stop it. Just stop it. And no, I don’t want to know how big or hard your penis is or how long it can perform — and I really don’t want to see a photo of it. Just. Stop. It.

So, that said — most of the people who ask for help are sincere, respectful, and sensitive to their partner’s desires and pleasure. Realize that our age and experience has not turned us into an alien species — treat us like valued human beings, interesting for more than sex. 

Leopardy is a 22-year-old male in Australia who likes older women. He emailed this story to me:

I’ve had 2 women in my life (sexually only). Great fun, I must admit, but it tears you apart when the bad has to come up. I like older women for their maturity and for their gorgeous features, such as lips, hips, legs, and fragrance, mmmmmmm. I admit I find it rather hard to find the perfect older woman as they all tend to lead me on then shoot me off which hurts like hell.

I met a woman online back in 2004. After 3 months chatting I gave her my details and she came up here. We had sex, and then she really got abusive and threatened me with police threats etc. She told her so-called friends about me and said what a pathetic useless peice of shit I was.

I’d like to know how to approach older women. I just want a woman that can understand me, one that takes me for who I am and NOT degrade me in any way.

Thank you for been so supportive and having a wonderful site. I can’t even recall how I got hold of your site, but I was amazed and immediately added it to my favourites.

Leopardy, I encourage you to get to know the older women who attract you before you jump into bed with them. Those who are looking for quick fun probably won’t value you the way you want. It’s fine to seek a match online, but if you seem to connect, please take some time dating and becoming friends so that you know who she is and she knows you.

That might mean you don’t get the instant pleasure and excitement of sex with a stranger who seems to fit your fantasy, but if what you’re looking for is a respectful relationship, that takes time to unfold and nurture.

That doesn’t answer your question about how to approach older women. I’ll repeat the suggestions I gave Sean:

  1.  Converse, listen (very important!), and flirt as you would with a woman of any age. Yes, she’ll recognize the signs. She might be shy about letting you see her signs, in case she fears she’s misreading yours, so keep her talking.
  2. Don’t rush things along — she wants to know that she interests you as a person, not just a potential bed partner.
  3.  Look into her eyes a lot. Really listen and respond to what she’s saying.
  4. Lean towards her to give the body signal that you’re interested. Watch for these signs from her: eye contact; leaning towards you; arms relaxed (not crossed in front of chest); playing with hair, clothing, or jewelry.
  5. After a nice, long conversation, where you feel there’s a connection, you might ask her outright: “I wonder if there’s any reason I should not ask you out.”
  6. If she says, “I’m old enough to be your mother,” you can ask, “I really like the maturity and intelligence of older women. The question is, am I too young to interest you?”
  7. If you’re really brave, carry a copy of one of my books. When she asks about the book, say something like, “I find older women very attractive, and I hope this book will help me understand them better — in all ways.”

I’d love to hear from readers about this topic. I know many readers come to my blog seeking information about older women/younger men relationships, so please contribute yours.

— Joan

M age 46 seeks F 60-78

Bravo on an interesting profile, and for being open to seeing a somewhat younger man,” the message from “desire4mature” on OK Cupid began. “There is no better match when it all comes together between the right older woman and younger man. He will be a lucky man. I admire from afar, and I wish you well.”Afar? Yes, really afar. My suitor, “desire4mature,” is 46, M, straight, available, and lives in London, United Kingdom (5335 miles from me). His message intrigued me, though, so I read his profile. It echoed the views of many men who have written to me for advice about connecting with older women — but with such an articulate flair that I wrote to ask him for permission to quote from it. Here are some excerpts, with his permission:

…I seek a mature, ageless, energetic woman for undeniable chemistry…physical, emotional, and intellectual chemistry …

You are better today than you have ever been, more alive, more free, more wise and more sensual, still with unquenched desires. You are most likely over 60, completely ageless in mind and spirit, smart, well-preserved and fun.

Are you are bursting with energy, but have difficulty finding a man your age who can match your liveliness? Do you want someone whom with whom you can be your true self, free and at ease, knowing you are accepted and desired no matter your age, with someone who accepts you as you are who sees your age and youthfulness and wisdom as assets to be treasured? … Can you envision yourself in a passionate and intense love affair with a smart, youthful man who sees you as the beautiful and amazing woman you have become, who values your wisdom and life experience and zest and passion, who can harness your deep sensuality and match your desire, with no insecurities, welcoming you to realize your true Goddess nature?  If so, I would love to know you.

You will feel and welcome my desire for you, for the woman you are today, not the woman you were 20 or 30 years ago. We both know how much better you are now, smarter, wiser, more accepting and free, more sensual and appreciative, more full of zest and life ….

“So how is that working for you?” I had to ask him, explaining that my inquiry was less from prurient interest than from wanting to inform those of you who keep asking me about how to meet older women. Is a dating site like OK Cupid a good place?

“desire4mature” listed for me the many categories of women who would not respond to his ad, or who would not interest him, leaving a precious few who became his friends and then lovers. He said in an email,

It is a very rare woman that I end up talking to for a longer periods of time and then meeting and becoming lovers. Sexual health is very important too, so again, it’s rare to get to that point for me, but I have, and have gloriously been rewarded to have known or know a small handful of truly amazing, incredible, sensual and beautifully sexual women, all 20 to 33 years older than me. I love and cherish them and always will.

My questions to my readers:

If you’re the older woman, could you see yourself getting involved with a man like this one? What sort of screening test would you use to decide whether he was sincere and a good potential bed partner?

If you’re the younger man, have you tried using an online dating site to find an older women who might be a good match for you?

If you’re a man of our generation, what do you offer women our age that a younger man does not?

I welcome your comments.


Update 10/7/2013: I just received yet another email from a young man — this one is 25 — who wants to date “a granny.” (I understand that in other countries, this isn’t an offensive term — though it makes me cringe.) His request for my advice had no caps, and many words were abbreviated (“frm,” “lyk,” “sm1,” “whoz,” “plz,” for example). If he won’t even take the time to communicate with me correctly, why would I think he has something to offer a woman my age?

Young men — it’s not that we’re not savvy enough to read your text-speak — we can read it. But approaching us this way does not make you appealing or interesting.  (For more info and a bit of ranting about this, please see this 2009 post.)

As always, I welcome your candid and thoughtful comments.*

* However, as always, do not try to hijack my readers to a toy store, escort service, porn site, or any site I haven’t endorsed. Those comments are deleted before seeing the light of day. I wish the spammers would stop making me cranky.

Breaking Rules at Our Age

What sexual “rules” have you broken since turning 50, 60, or beyond?

I ask this because I discovered from the interviews and reader stories that you’ll read in  Naked at Our Age: Talking Out Loud about Senior Sex, many of us make some pretty drastic changes in our lives after age 50. Maybe we get divorced,  discover love, open up our marriage, take a new lover, experiment with kink or multiple partners or virtual sex — or some combination of these or other alternatives.

The point is that although society sees us as settled into mid-life or old age, we’re far from “settled.” I think there’s something about emerging from menopause that makes us question where we want to be in our lives. Menopause often feels like an upheaval — I’ve described it before as “PMS on steroids” — where everything seems upside down. We don’t want to be responsible for remembering the whole family’s appointments, for example, and we might not be overly kind when we tell family members to take care of themselves.

After the upheaval settles, we see our lives differently. We realize that it’s now or never: it’s up to us to invent — or reinvent — what we want the rest of our lives to be, and what we have to do to actively go after our dreams.

At the same time, in our sexual world, the old ways may not work any more. We may need different kinds of arousal or even a different type of relationship or a different partner. Major!

I got so many stories from my Naked at Our Age interviewees about alternative sex practices that this topic became a whole chapter: “Off the Beaten Path: Nontraditional Sex Practices and Relationships.” People wrote about swinging, polyamory, BDSM, friends with benefits, older women/younger men (20-30 years difference!), phone sex, and more.

I predicted that younger readers would be shocked at what seniors are doing behind closed doors, and I should have guessed that it would shock our own age group, too. I’ve heard a couple of criticisms that this chapter and the one titled “Hiring Sensuality” (which I won’t tell you about — you have to read that one for yourself, and no, it’s not just men hiring sex!) make it sound like I’m endorsing or even pushing people towards alternative lifestyles.

I’m not pushing anyone into anything. I’m showing senior sex — behaviors and attitudes — in all its colors and stripes. Personally, I support adults doing with other consenting adults whatever brings them pleasure, as long as it doesn’t hurt anyone — including the partners of those consenting adults. I have “vanilla” tastes myself, but that’s beside the point. The book is only partly about me. It’s really about you… and you… and you.

So back to my original question: What sexual “rules” have you broken since turning 50, 60, or beyond?  By rules I mean society’s rules, the law, unspoken or spoken rules in a relationship, even your own rules. I’d love to see a dialogue start here. Please comment!


Naked at Our Age: Talking Out Loud about Senior Sex is now available! Order an autographed copy directly from me, or order from Amazon here.

Learn more about Naked at Our Age: Talking Out Loud About Senior Sex here.

Andy, 44, turned on by women 60+

I often hear from younger men who tell me they desire older women.

Sometimes their emails are short and consist of abbreviations (hey, guys, emails to me shouldn’t read like a tweet!), which makes me wonder how they would handle a slow-burning, older woman.

Occasionally they invite me to share a romp–or, in one case, a shower. Sorry, fellows, I’m flattered, but I need to get to know (and like) a man first.

Usually, though, they’re the kind of reader emails that I love: respectful and earnestly trying to gain useful information or share a story. For example, I recently heard from Andy, age 44, a British man who gave me permission to share what he wrote me:

I am exactly the type of man you so often write about. When I was just 15, I would look at my mother’s friends and fantasize. Later on at night I would lie in bed and imagine making love to them. I would conjure up scenarios in my mind and imagine the spontaneity and excitement of it all.

As I get older, I find myself wanting women of 60-plus. My mates think I’m strange, weird – some even think I’m sick. But what turns me on is not so much their physical appearance but that they are so turned on themselves during the course of our love making.

I would far rather make love to a highly excited 60-year-old woman than a drop-dead gorgeous figure of 22 years who acts like a mannequin.

Right now, I am finding myself flirting with an older woman yet again. She is 70 and clearly very sexually frustrated. She flirts with me and has said in no uncertain terms if she was 30 years younger she would be “hitting on me real hard.” Wow – I got so turned on when she said that. I think something might happen soon.

I suggest he tell her, “You don’t need to be 30 years younger — you’re perfect the way you are!”

Anything you’d like to say to Andy?

For more posts about younger men/older women, click here.