Roger, 32: how to talk to older woman on train?

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.

“im 19 looking for an older granny”

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.

Becka, 70: Internet dating winks, flirts, and peeves

Becka, 70, the most active member of my senior online dating posse, has been trying to puzzle out the internet dating maze. Here’s her third report:

Trying to decode the mystique of the internet dating scene is a little like being lost in the middle of a Dan Brown book. “What does it all mean?” you ask yourself – many times.

My first piece was titled “Wading Into the Senior Internet Dating Pool.” I erred. The experience is more like being thrown fully clothed into the deep end of your neighbor’s pool which has not been cleaned for months!

I’ve discovered that these dating sites pad their numbers by keeping people on the rolls who have not visited in months, in some cases, years. They are, in effect, ghosts and will not, of course, respond to your inquiries.

Despite the ghosts, I have received a slew of responses. Some men who liked my profile responded right away and a day later sent me petulant “pokes” as to why I had not answered. Hold yer horses, buster! I’ve yet to figure out both the etiquette and the technology of this thing. But one thing I do know, I’m deleting the guy, age 65 who is looking for a woman 40-60!

Some of the choices you have for communicating are “icebreakers,” “winks” and “flirts.” I don’t know about you, but I’ve never winked at a guy in my life unless he was under the age of 8. If you are 60 or older, chances are you will not be comfortable taking the aggressive role. Okay, go to your corners and come out flirting! Luckily for you, it’s all anonymous. That makes you braver than you thought you’d ever be with men you don’t know — and might not want to know.

Some peeves:

  • Senior Match encouraged me to fill out a personality form only to disclose that I could use it if I paid. I didn’t like the subterfuge. But I’m finding out that if you don’t like subterfuge, don’t try internet dating.
  • A number of guys had signed up with two different user names, so if you rejected them once, you get a second chance to reject them all over again.
  • On all of the sites I found links that didn’t work, windows you had to check but they didn’t drop down for you, and pages that would not come up.
  • On one site I could not choose my state and so I received a dozen interested queries, the closest being from a man 750 miles away.

But I soldiered on and learned some surprising things.

Thank you, Becka! Coming soon — what did Becka learn?

Would you like to join our senior online dating posse and report on your internet dating experiences for the education and entertainment of our readers? Email me.

Note from Joan: I apologize for posting about a particular dating site’s special free weekend offer recently. I don’t know if the site was overloaded or what, but one reader reported that after spending forever filling out the long questionnaire, the site gave an error message. She wasn’t about to start all over again, so she emailed customer service to find out if what she had done was saved so she could continue from there. She got a form email telling her to phone — but no one manned the phones on the weekend, and the free offer would be over by the time the phones opened. She gave up and receives frequent solicitation emails from them now. I deleted my post about the site’s free weekend, so don’t bother looking for it. I’m not naming the site now because I don’t know if this was one person’s freak experience or that’s what happened to many of you — let me know.

Widow’s personal story of “touch deprivation therapy”

Ellen Taft wrote me this moving email and gave me permission to publish it here:

I can’t thank you enough for all you’ve done to help me get back out there again after losing my husband of 37 years in December of 2007. I’m 63 today, and it’s been a terrifying and exhilarating experience.

My husband died a year and a half ago. It had been over 40 years since I’d dated. Getting back out there has been a real trip! But I’ve done it, largely with the help from Joan’s book, Better than I Ever Expected, and her blog here with the wonderful information and links. The link to Judith Sills, and her book, Getting Naked Again, gave me the final push.

Sills suggested having a friend “mentor” your reentry into getting naked again. So that’s what I did. I asked a dear friend and fellow recent widower to help me in this tremendous step. We had been dating for a few months, very cautiously, as he is a more recent widower, and not ready for any new relationship, but this mentoring idea appealed to him.

We “negotiated” which means we clarified just what we were doing and why, so no one would be mislead. We shared our feelings about our bodies, what we needed the other to know, our limitations, and our fears.

I asked that we use condoms or get tested for STDs. It was an amazingly honest and open sharing, and I attribute the comfort level we experienced to our “negotiations.” Once we knew these intimate details about each other, the concern and caring that followed made the whole experience positive.

I had done a lot of reading, too, including Michael Castleman’s Great Sex, also mentioned in Joan’s blog, and all my reading paid off.

It was a wonderful, amazing three hours. Neither one of us could believe how smoothly it all went. We both enjoyed it so much and were so relaxed we have continued the relationship. We call it “Touch Deprivation Therapy,” and oh, how it helps!

Thank you, Ellen. I’m thrilled that you shared your experience with us and that my book recommendations helped you! (Read these and my other book reviews here.)