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:
- 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.
- Don’t rush things along — she wants to know that she interests you as a person, not just a potential bed partner.
- Look into her eyes a lot. Really listen and respond to what she’s saying.
- 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.
- 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.”
- 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?”
- 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.
Well, here’s my story. I was in college, age 21, and in one of my classes was a “non-traditional student” (that is, not straight out of high school). I later found out that she was 36. I had had a high school girlfriend (no sex) and a boyfriend in my freshman year (lots of sex; we were broken up by geography). I was kind of prickly and arrogant in those days, trying to cover up my basic shyness. Gale saw through it, though, and we became friends and then best friends. I would hang out in her apartment, and as we were talking I would lose track of when I had to leave to go home, so I missed the last bus a lot! I slept on her couch a lot as a result.
Eventually Gale took a short-term job house-sitting from a friend she had known for 10+ years (still a friend today), and talked with her friend about me. By that time I was pretty infatuated, and Gale’s friend encouraged her to “go ahead and have a fling”, even if one of us lost interest later. So she invited me to move from the couch to her bed. At first it was all cuddling, and then various sexual things. I don’t actually remember “my first time” clearly, except that orgasmically it was a flop, and it took months for me to be able to come with her — she didn’t have that problem with me, as it turned out that my oral-sex skills and attitudes with my boyfriend were mostly transferable.
Anyway, we found we were in love, and pretty heartbroken when I moved away to go to grad school. That was another flop, and when I called her up saying “I’m leaving school”, she was pretty angry with me for assuming I could just move in with her. (Actually I didn’t, I was too naive to realize she would naturally think that.) But we talked it out, I got a job pretty easily, and we lived together for five years before getting married — best wedding I’ve ever been to! She kept warning me: “What are you going to do when you’re old and I’m older?” We just laughed about it.
Another five years, and we adopted a baby girl. She grew up to be a difficult child, and it was a more or less constant struggle, but Gale and I bonded even deeper than before. We encouraged her to always bring her boyfriends home rather than take risks in other people’s apartments (she was raped once by a boyfriend’s “friend”) and as long as she stayed on her contraceptives and used condoms, she could do what she liked in her own bedroom.
When our daughter became pregnant (different boyfriend, thank heavens), the father moved in with us, as his parents were dead and he was living with an aunt who tolerated him at best. After a few years they broke up and he moved out again. Eventually she met someone (a childhood friend she hadn’t seen for years) and they have three babies now and another on the way. (She swears she’s getting her tubes tied *this* time. We’ll see.)
So now I am 64 and Gale is 79. Three weeks ago, Gale had a stroke at home and was admitted to the hospital. There were a series of complications, and although she’s past the worst of those (pneumonia, a cardiac stress event — like a heart attack, but the heart isn’ t damaged physically — partial kidney failure, etc.) she still doesn’t talk and she doesn’t know me. I go to see her for a few minutes almost every day — some days I can’t bear to. There is no telling how quickly, or how much, her mind will recover. I miss her far more than I can tell you. I feel like a plant ripped up by the roots.
But this is a story about a lifetime of joy and sorrow, and it isn’t over yet.
This is quite a story, John. Thank you for sharing it. I wish you and Gale the best.
In June 71, I was 20. My girl friend was 46. We were somewhat high status individuals in a self awareness expansion organization. (it has since morphed into a somewhat infamous cult). We studied together. We also hit the movies frequently. I was a farm boy, with not very much sophistication. I drove a 1950 Plymouth. She was blue blooded with a masters degree from Berkeley in archaeology. Her ex husband was president of Otis Elevator. She had a son six months younger than me. We had a hot relationship for years.
She's still one of my best friends. This year, 2016, she turns 90 – still sailing (wind , not motor), skiing, gym near daily, travel, CATO Institute, etc
I think I graduated cum laude in cunnilinguistics from this period of my life. She filled a hot bikini.
We lived together for four years, alternating between her house and mine.
I shared Cat's Cradle by Kurt Vonnegut, Jr. with her. She taught me Greek and Latin.
We, both, enjoyed working on one another's homes together.
both of us were (and still are) libertarians with interests in gold and silver investing and political economics.
It isn't that she was older, and I was younger. We simply were mutually interested and in common reality on dozens of subjects ranging from intellectual and "new agey" to reading mysteries to gardening and wall papering.
There weren't any boundaries due to age. There still aren't.
I think the interesting thing is that is seems from pornhub statistics young men seem to be interested most in "milf", "mom" and "mature" women but in the culture generally an older woman with a younger man is still such a hot and taboo topic while older men with younger women is not.
It was odd to see the reactions to the Dressmaker movie with Kate Winslet (1975) sex scenes with Liam Hemsworth (1990) or Demi Moore dating Ashton Kutcher and the examples could go on and on and on and on…….
Over 30 years ago, when I was a young lad of around 23, I had a wonderful relationship with a woman in her 40's. We met because we were both part of the same social organization, and thankfully she was the one who made the first move. Yes, the sex was phenomenal, and yes, I learned a lot from the experience. But what made it work was that it was a personal relationship first, and the sexual part evolved naturally from our personal chemistry. To this day, I have only fond memories of those days, and am delighted that I got to reconnect with her a few years ago.
So, let me add my advice to the young men who find themselves attracted to older women – good for you, and go for it. There are so many amazing benefits of such a relationship, not the least of which can be a vibrant and passionate sexual side. But look to find a RELATIONSHIP first and foremost, and if (and only if) that works, will the sexual side be truly exciting and fulfilling.
Good luck to you in finding all the joy and happiness you can in a relationship, no matter the numbers.
I love this comment more than I can say, Jeff. Your advice is perfect. Thank you for posting it.
Of course, Joan. The pleasure was all mine. (Okay, maybe not all…)
Thank you, Dan and Anonymous, for adding to the conversation with these thoughtful comments.
I was thinking back over this and re-read my comment above and apologize for the grammar and spelling errors. I just typed it out quickly.
But I was reflecting back how in elementary school, middle school, high school, and college as I was becoming aware of and interested in girls/women, I was interested in the girls my own age but I was also very aware of or had the hots you could say for and fantasies about quite a few mature female teachers.
And during this spectrum of age ranges I was aware of quite a few very hot mature friends of my mom and hot moms of my friends and hot moms of a few girl friends.
I think this is a universal experience of most or all young guys growing up. I think it is no accident and very telling that a huge amount of porn models are over 30, 40+, 50+, and 60+. With a huge amount of porn being young guys with older women over 30, 40+, 50+, and 60+.
I had been with few young girls so I wasn't a virgin, but my first time with an experienced older woman when I was 18 blew my mind with the most incredible blowjobs of my life. And she was the first to let me in her backdoor which was a wet dream/fantasy cum true. It was hotter and tighter and naughtier and more wonderful than I could have imagined. She was an incredible life changing sex teacher.
She was recently divorced and needed her lawn mowed. Then needed something out of her attic…
She said later that she had been aware for some time that I was always checking out her feet, legs, and ass.
Speaking personally I've since dated many older and younger women. My first wife was 8 years younger and my second wife now is 13 years older but for me all of the older women are hotter and sexier and have something about them. There is really something about the beauty, maturity, and sexuality of women 40+, 50+, and 60+. And young men like it.
I certainly don't have the answers, but as a younger guy that likes older women, I think there is a universal experience for all guys or young men that as they're hitting puberty or even earlier when they're becoming aware of women from society, t.v., movies, daily life experiences young men see older mature developed women who wear make up and wear heels etc. is their experience of older mature women as the example of womanhood and sexuality.
In our culture through advertising etc. the younger skinny girl is the object of beauty. But if you look at the girls/women men prefer, and what they like in porn is a good example of what men really refer, many "models" are a bit older and a bit heavier than the run way model.
I think this is the reasons for the typical fantasies of young men about their teacher, mom's friend, older neighbor, etc. In some cases a young man may have had some sexual encounter with an experienced older woman that was amazing as was my experience. I'm now married to a woman 13 years older than me, she's 54. My first experience, when I was 18, with an older woman , who was 42, was a divorced neighbor who always wore mules heels. I think they should be called "f@#% me" heels!!
But I think this goes for women or young girls too who like older men like George Clooney etc.
Plus an older person male or female is more experienced and perhaps more confident in life and in their sexuality and that is attractive like yourself Joan.
I, too, love older women. If they are hot, I flirt with them. At 65 I was chatting up a woman I found attractive at a poetry reading recently. She was so funny and alive and was dressed and painted up to play.
"You know I'm hitting on you, don't you dear?"
"Well, sure honey. And I count it a fine complement. But you might want to know however that I just turned 84."
"Well, dear, I'm 65. I'm old, too. I just think you should know that you've still got it going on and I think you're hot."
It was thrilling to flirt with her and I was/am sincere. If my wife gave me a pass I'd get a little hot tub forward and naughty with her in a minute. Relationship? No. Friend? Yes. Friend sex? I don't do that so I couldn't say. But if I did, I don't know why not. Kinky? Maybe.
Thrill and flirt and sex anything is ageless I think. Love? Relationship? Enduring, hot and soulful sex? Not so much.
Dating at age 54 I had a five year window up or down max rule; and when I closed out 5 yrs dating and married at 59, my wife was/is–no shock–three years younger than I.
You raise good questions Joan, reminding us that sex may be easy and love hard; but as we get older, both take more care and work and intention to do well.
"Confused," thank you for returning to add more. I'd love to use your story in my new book, Naked at Our Age. I have a whole chapter on Younger Men, Older Women.
Would you please email me (firstname.lastname@example.org) and I'll let you know what's involved?
Ditto for anyone else reading this who has a Younger Men, Older Women story or questions!
Joan…thanks for your time and care in responding!
Well…and I don't think I was clear…so it's my fault…we've had actually two dates. The second was where the sexual discussion occurred. So…we're definitely getting closer. I know she's interested in that…and I am as well. I just have never been with someone so much older. I know…from reading your blog today…it's nothing different at all. But…I don't know if there's any permanency to our relationship. We do feel some strong sexual tension though. The other thing is this…and I'm sorry I didn't mention it in my last post. We never discussed her age, and on her profile it says "62". After we met…I well, googled her cuz I was curious. And…I have reason to believe she is actually 72 years of age. I would have never guessed…and I know age is nothing I would ever bring up. But still…it's leading to the general confusion in my mind. The kisses are electric…I like how it feels when we touch…but the 40 year age gap potentially just jumps into my head in a strange way when I imagine making love to her. Ugh…what a conundrum!
"Confused," thank you for commenting here. She has given you clear signals that she's interested in you. why not just date now, get to know her, see how things go after the first date?
She told you she's interested in you sexually, but that doesn't mean the next date has to be sexual. Get together and plan an activity together that you both enjoy. Talk some more. Kiss some more!
It's far too soon to be worrying about commitment when you've just had one date and some online messaging. Get to know each other in person now.
Hi there~I'm a 32 year old man in the midwest. I'm single and not dating anyone right now. I decided to try my hand at a dating site and a woman that was 62 messaged me. She's incredibly interesting, intelligent, and very pretty. I was somewhat uncertain about the age gap. Anyway – we met once and actually we kissed at the end of the date. We had a playful discussion recently in which she said something, and I responded that I would marry her if she did something (it was a humorous talk). Anyway – she mentioned that we should see if we have sexual chemistry which kind of took me by surprise.
I feel guilty about getting together…and maybe having sex. I am definitely intrigued and attracted. I go back and forth all the time. I don't know why I am wrestling with this. I know we're both adults…but I just can't get over this feeling. Her age does weigh a little because I'm not sure I want to have a committed relationship. But – I do like her…and I am definitely sexually intrigued. I don't think I'll get an answer here – but what do I do?
I want to add yet another comment, and promise to keep it short!
Younger guys need to make it clear, somehow, that they're seriously interested in dating an older woman. Asking her to "go have coffee" is a good start, or something like that, and everything Joan says about conversation and getting to know each other first is right on.
I've run into flirtatious younger men who only wanted to flirt and didn't want to do more. It can be really embarassing to find out that he wasn't really flirting seriously. Maybe he thought since I was older I was safe to flirt with and wouldn't expect more? Maybe he wanted to practice? Maybe he wasn't really flirting? I assumed that these attentions were more serious, and it was a big blow to my ego to find out they were not.
Consider too that the older woman may assume that the younger man isn't serious and is indeed just practicing or not really flirting. She may not realize this is for real and act accordingly, making it harder to get a date with her.
Paula, that’s a very astute revelation you’re having: yes, men can be hurt by love and sex, too. My guess is that the kind of man who posts here on this blog is, in fact, the kind of man we all want to know: respectful of women (especially older women), introspective, communicative, vulnerable, and willing learn and to love deeply.
Of course, I wonder what “older” is to a 22-year-old. Remember that song, “Older Women Make Beautiful Lovers”? Wasn’t he praising “older” of 35? Or something like that?
“Older Than 35”
I’m wondering some more.
Have women as a whole come to view men as people who can’t be hurt, who are never the victims of love gone wrong? Do we see them as adversaries in a way?
I think I myself have had these views. The thinking goes something like this, “men almost always hurt me, they don’t care, they just want sex.” It can follow from there that it’s okay to hurt back, or to simply be careless with someone’s feelings, and that can be misdirected at someone who doesn’t deserve it.
This post and comments point out the important fact that men are as emotional about sex and love as women, albeit in a slightly different way. This is something I for one need to keep in mind.
Joan has it down with how to flirt and get to know someone, except keep the book at home. I’m sorry but a guy who brought along his how-to book is going to come off as a nerd, no matter how wonderful and cool he really is.
I think running into “crazies” (emotionally unstable or even abusive people) is a problem for both genders and people of all ages. All the more reason to get to know someone well before you have sex with them.
I wonder if older women — generally speaking — don’t view an affair with a younger man as more of a fling, and something temporary. I would always think, “well he’ll eventually meet someone his own age and that will be that, might as well enjoy this while I can.” Maybe we need to take younger men more seriously as potential partners for a more committed relationship.
I certainly don't view my five year and counting deep emotional and sexual connection with my now 31 year old lover as a fling. I am 56. It happened. It was undeniable. Both of us had our trepidation and our confusion, but whatever… We are not now living even in the same country, but the connection still sizzles. We hope to get together again when circumstances permit. He fulfills a space in my heart that my husband and my lifelong soulmate do not. It is what it is. I have received so many gifts and so much joy from this intensely sexual connection. It is also emotional and intellectual. There are so many layers. I am compiling a book of poetry about it. The pain during my departure, and his innate inability to face up to what it meant. And yet, here we are two and a half years later, and the connection not only exists, but has intensified, as he has begun to more honestly acknowledge what I mean to him, and he realizes that his desire for me is if anything more real in his heart. It is not going anywhere, apparently. So. Nope. Not fling oriented in the least. Let's try not to generalize. There are as many types of bonds as the re are people. The whole mystery of sex and relationship is that they bring out so many unpredictable aspects in each other. Let's just celebrate the mystery and the diversity and the surprise factor. And YES, if I could find anyone even remotely interesting, passionate, and seductive as my flover, I would happily engage in another relationship. Sigh. I think they only show up every five years or so. I am long overdue!!
I also think the older woman/younger man situation is still quite taboo. My lover is a lead singer in a rock band. He is totally hot, whereas I, as an aging, disabled, overweight woman, am not perceived as by social standards, as anything special. In the bedroom? Volcano. Dynamite. Blazing forest fire. You catch my drift. I get dismissed all the time for how I look. It is difficult to accept that he just cannot include me in his social life as anything other than a friend and-get this-former landlady. Yep, we were roommates first in a home where I rented rooms to college students. AWKWARD! Anyway, his social acceptance as sexual napkin is fine and dandy. Mine is not. Well, I plan to do something about that, and when my poetry gets published, the memoir to follow will be pretty same awesome and will definitely change a few people's preconceptions. It is time to let our aging freak flags fly. In my opinion, it is because we hide and remain silent that people don't know how to approach or handle the different needs and expectations. Education. Permission GRANTED. Once we start swarming out of the woodwork, I foresee major societal changes in terms of how we are treated, how we treat ourselves, and yes, we who are brave enough to step forward and show our faces get to craft a new normal, where people get to be people and not closely defined roles. Enough with the shame and judgmental attitudes.
SophiaB, you've added a lot to this discussion. Too often people are dismissed / judged on the basis of looks and preconceived notions. You're helping to break that stereotype. Thank you.
hi im a 20 yr old male and i gotta admit older woman are better than girls my age – older girls know how to treat a man and i been with one for a while and she looks after me and takes care of me when it comes to everything! – i respect her and i treat her how i would like to be treated – shes 20years older than me and i dont see age as a problem because shes a really nice woman deep down inside,im happy and i believe thats all that matters.shes taught me alot of things that only a woman can tell – older woman are beautiful LOVERS!!
Lonely, I found your comment so compelling that I devoted a whole blog post to it at http://betterthanieverexpected.blogspot.com/2008/01/what-to-do-when-your-sex-drives-arent.html.
I am 38 and have been with my husband who is 42 since I was 17. My husband used to want to have sex every day if not more often. I of course did not want it as often as he did but tried my best to accommodate him for many years. Around the time I turned 35, I noticed a huge jump in my sex drive, I would say 3 times a day, every day would now satisfy me. All I think about it sex and my orgasms are explosive, usually having multiples back to back.
What I am writing about however is my disappointment with my husband. It seems our roles have reversed. He no longer wants to have sex as often, mainly only on the weekends. I am very frustrated. I thought this is what he wanted all these years, a wife who wanted to have sex as often as he did. He claims he still wants me and wants to have sex but, gives a long list like I used to as to why “now” is not a good time. Is there any hope his sex drive will return?
It seems unfair to give myself to a man all these years and not have him reciprocate. I feel resentful, rejected, and hurt. I have always been faithful to him. However, I admit I fantasize about an affair or even leaving my husband for a younger more virile man. It would be nice to have a man keep up with me, not fall asleep on me. Yet having been with one man so long, I worry that a younger man would not find me attractive, or only want me just for sex. Is this true? Are there sexy men out there in their twenties that want a woman my age?
If I end up staying with my husband I think I should to go back on the pill or something to rid myself of my sex drive. I’d rather not have one then to feel this way. Is this it? If I stay with him will I be subject to years more of frustration?
Lonely in Thirties
Chris, that’s wonderful that your first experience was so satisfying, and with an older woman! I’m sure some older women seeking younger men do hang out online, but speaking as an “older woman” myself, I would much prefer to meet a man in person during an activity that we both enjoy and let the relationship evolve if the sparks fly during conversation. I suggest you engage in social activities you enjoy where older women are plentiful, and get to know them as people first.
When I was in my early fifties, I had a marvelous series of interludes with a man half my age. I met him dancing, one of my favorite activities. When we danced together the first time, I was enticed by his natural scent — I felt powerfully attracted and wanted to dance closer.
We started conversing, and a few days later, we were lovers. (Yes, I jumped into sex more quickly in those days!) It wouldn’t have happened if we hadn’t met in person engaging in a common interest.
HI my name’s chris and i’m 18. i just recently completed a life long dream of having an older woman take my virginty and teaching me the ways. Thing only thing is it was a one time deal but now i’m hooked on older woman i love their maturity and knowledge. The only thing is i’m not sure of any sites where i can meet and talk with them. Evrywhere i find is you have to pay, and i don’t believe that i should pay for love so can anyone help me thanks chris.
Wow, what an experience, I know other people who have met people of questionable character on line, so I agree with Joan on being careful about that. Not that meeting on line is necessarily a bad idea, but, yeah, definitely get to know the person before you have sex with them.
My former massage therapist, a wonderful man about 15 years older than me, once told me that if I wanted to know if a man was going to stick around, make him wait for sex. If he will, it’s likely he’s there for a respectful relationship, not just a one nighter. I think that rule could apply to anyone, and could apply here.
I think in general older women have a different agenda for the men in their lives than younger women do. Younger women are looking for someone who would be a good daddy as well as a good partner and lover. Even if we consciously don’t want children, we still have this “mommy brain” when we’re in our younger years. Older women are just looking for a good lover and partner, or maybe just a good lover.
Older women, in spite of having a simpler agenda, are generally more picky about men. We’ve learned through experience what we want and don’t want, what we like, who we’re looking for. So younger guys should not get discouraged if they’re turned down a few times.
I wrote more about older women and younger men in my comment on the story about Sean.
Joan is right on with her flirting advice!