Two years ago, Roger, age 32, took the subway to his job everyday. He was attracted to a woman he guessed to be in her fifties who took the same train. “We used to flirt,” he writes me, “Which was easy to do on a crowded train with a lot of bumps and turns, especially when we stood/sat shoulder to shoulder.”
They never spoke a word but always found themselves next to each other for the trip. “In such public places it was hard to approach and communicate and the attraction never went beyond that,” he writes. “I’m sure we were both hesitant because of the age difference. Also, I was a virgin at the time and somewhat timid.” (He has since had sex — once! — with a woman his age.)
Then he left that job and no longer took that train. However, two years later, he is working downtown again, and he writes:
The dance on the subway has once again begun. Aside from the physical attraction, we seem to have a genuine interest in each other and I feel like I’m mature enough for her. I’d like to get to know her, but I don’t know how to gauge her interest in getting to know me.
Is she looking for a relationship? Am I? If we’re both looking for mostly intimacy, is that ok? I’m concerned about being seen in public, but how do I know if she would also want to keep it discreet?
I know the first step is to talk to her, but I don’t know how. Do I talk to her on the subway, or might that make her uncomfortable? Should I slip her a note? I only had sex with my girlfriend once and found it mediocre. I’ll admit I’m very attracted to this woman and love the idea of her ‘teaching me’ but I’m worried that she’s interested in much more and would think I just want sex. Any advice you can get will be greatly appreciated.
I don’t think you could manage to find yourselves shoulder-to-shoulder every day on the way to work if she weren’t as interested as you are. The way to talk to her is, well, simply to talk to her!
You could start by bringing up the coincidence that you’re taking the same train again, two years after you “met.” It almost doesn’t matter what you say first, just talk to her. If you need an opening line, how about “It’s the high point of my day when you’re on the same train. You must work downtown, too.”
One point you make is a red flag for me. You worry about being seen in public. Why ever would that be an issue? If you’d be ashamed or embarrassed to be seen with her, then please, for her sake, don’t approach her at all.
It’s one thing to hope for an intimate, no strings relationship where she “teaches” you — a young man’s fantasy that can come true! But it’s another to be worrying about hiding the relationship before it even exists.
Roger, you seem like a very nice young man, but I don’t think you can claim “maturity” as your best asset — not because of your age, but because you’re so shy about saying a word to this woman. Get to know her. Let her get to know you.
If she’s interested in just taking you to bed and then switching trains and never seeing you again, she’ll take that initiative. But if she’ll find you interesting, funny, or sweet, then do open your mouth and let her know who you are.
Otherwise the years could roll by along with the train.
hey joan im 19 looking for an older granny that i can meet and have a relationship with.how can i do this
This is an actual email I received, similar to others, unfortunately. Instead of simply deleting it, I’m going to answer this question once and for all:
1. I don’t know any sexually inclined women of our age who respond to being perceived as “an older granny.”
2. We grew up being educated to use capital letters at the beginnings of sentences, names, and for the word “I.” Not doing this makes you appear uneducated and/or in too much of a hurry to bother. If you’re in that much of a rush that you can’t press the shift key once in a while, think about what you’re conveying to an older woman as the kind of sexual partner you’d be.
3. You may have found me by skimming my blog, but you obviously didn’t read it carefully or you would have seen the “younger men older women” label, with several posts on this topic. Read them!
For younger men who have a serious and respectful interest in a relationship with an older woman who might be open to you, I’m going to reframe some points I’ve made before:
Get out and do the social activities you enjoy, where you’ll meet women who enjoy the same activities. That way, it’s easy to strart a conversation with a stranger because you already have something in common to talk about.
Once you spy a woman who attracts you, do NOT use the “Hey, you’re hot and I love older women, wanna go to my place?” approach. Instead, open the conversation with comments on the activity you’re sharing or ask her for advice, e.g., depending on where you are and what you’re doing,
(Dance venue:) You’re a really good dancer — would you dance the next one with me?”
(Bookstore:) “Have you read any books by this author?”
(Gym:) “Your workout is obviously working for you — you look terrific. Do you recommend the aerobics classes here?”
(She’s reading a Kindle:) “Oh, you have a Kindle! Do you mind telling me how you like it?
(Park:) “How far does this trail go? Does it loop back or will I get hopelessly lost?”
And so on. I based these examples on activities I do, places I go, and comments that would get my attention and start a conversation. Of course you need to modify the topics by what you’re doing. (I’m only covering face-to-face meetings here — online meetings are entirely different.)
Most important advice of all: You may be hoping to share the sheets with an older woman, but you need to show her that you appreciate her as a person and value more than her genitals. You also need to show her that you’re an interesting person yourself. Remember that her most vital sex organ is her brain, and you’ve got to make contact there first.
I get frequent emails from men age 19-40+ who are attracted to women age 50-70+. They ask me how to meet women who might be open to a relationship with a much younger man.
I also hear from women who are surprised by — and welcome! — a younger man’s interest, and others who would rather not date someone younger than their son. An example in that last camp is “Granny B” who describes her blog this way:
GrannyBoogies on the highway of life!
The life and adventures of a senior woman looking for her last Love. Is there sex after 70? Do senior dating services work? Will Granny find her soul mate?
Granny B recently posted about being pursued by a younger man via an online dating site. I posted this comment on her blog:
On my blog about sex and aging, I hear from younger men all the time who are attracted to older women and ask how to connect with them. These men say they value the woman’s experience, self-knowledge, ease of communication in and out of bed. If you’re honestly not attracted to a man younger than your son (every man is somebody’s son!), then you’re right to send him on his way gently. But if you’re intrigued, you might get to know him!
Many of the younger men who write me describe warm memories about being introduced to sex by an older woman. Others tell me they respond to the wisdom and maturity of an older woman.
Check out my other posts on this subject.
Note to the men who want to talk about this. Yes, I welcome your comments here and your emails to me, but please — we’re talking about this subject with dignity. Do not send me your masturbatory fantasies or make me the object of them! (Please don’t be insulted by this request — I’m only saying this because it has happened a few times and that’s not what this blog is about.)
I hear from men frequently who want to date older women and ask how to find/ attract/ approach the women they desire. I hear from very young men (teens and 20s) who had their first — and wonderful! — sexual experience with a much older woman and want to recapture the joy. I hear from men in their 30s and 40s who are drawn to the wisdom, experience, and beauty in women decades older. For example, TW wrote me recently:
I am a 41-year-old male. I don’t have any problem attracting women around my own age. That is fairly easy for me. But, I do have great difficulties attracting women who are much older than I am.
I am mostly attracted to older women who are in their 60s and 70s. I am not looking for a serious relationship. Just casual dating with someone I can see occasionally with the possibility of intimacy or sex. I don’t where to go to meet older women. I’ve tried some internet dating sites. The women on those sites respond by sending me an email telling me that I am too young or that they have a problem with the age difference.
I welcome anyone’s ideas and suggestions. Especially from men who have had successful experiences with older women. Also, I greatly welcome any suggestions from older women themselves.
Personally, I advise TW to get out and do the social activities he enjoys, where he’ll meet women who enjoy the same activities. That way, it’s easy to strart a conversation with a stranger because you already have something in common to talk about. Someone like TW would meet someone like me, for example, social dancing or at bookstores, coffee shops, gyms, walking trails, and vegetarian restaurants.
Once TW spies a woman who attracts him, I would NOT suggest the “Hey, you’re hot and I love older women, wanna go to my place?” approach. Instead, open the conversation with comments on the activity you’re sharing or ask her for advice, e.g., depending on where you are and what you’re doing,
“You’re a really good dancer — would you dance the next one with me?”
“Have you read any books by this author?”
“Your workout is obviously working for you — you look terrific. Do you recommend the aerobics classes here?”
And so on. You may be hoping to share the sheets with her, but you still need to show her that you appreciate more than her genitals. Remember that her most vital sex organ is her brain.
Readers, I invite you to add your own experiences and tips for TW. If you are a 60+-year-old woman who would delight in a fling with a man 2+ decades younger than you, how would you suggest that someone like TW find someone like you? (I’m not offering to play matchmaker, realize, just wanting to help TW know where to look.) If you’re a man who has had experience dating older women, please share your experiences.
You can post a comment here, or email me and I’ll post it for you. (Try to ride the thin line, please, between candor, which my readers like, and graphic details/street language, which they do not!)