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.


  1. paula on November 4, 2009 at 1:20 am

    You're welcome Joan, and thank you for the nice compliment.

  2. Joan Price on October 31, 2009 at 9:36 pm

    Great advice, Paula! Thank you for taking the time to craft such a wise reply.

  3. paula, 57 on October 31, 2009 at 9:04 pm

    Roger, why not ask her if she'd like to go have coffee, or maybe a cocktail after work? Just ask her to go somewhere with you that's not necessarily a date. Go someplace where you can talk easily, as in not too noisy. A safe get together the way two friends would do. Taking away the pressure of it seeming like a "real date" is conducive to conversation, and perhaps she'll be impressed that you're being such a gentleman. (I'm always impressed with gentlemen in any situation.) Then you can see where it leads.

    You could say something like you've heard there's no such thing as a coincidence, and here you two are on the same train almost every day. When you're somewhere with both of you sitting down or taking a leisurely walk, ask her what she does. Ask her what she's interested in. Ask her if she has pets and what kind. Ask her what she does on weekends, and be ready to hear – perhaps – that she spends them with her boyfriend or her husband and kids. At least she'll probably be flattered by the crestfallen look on your face. At best you'll likely find out if she's available.

    I once wanted to get together with the teaching assistant for my senior painting class. I didn't see him all the time and I was about to graduate, so I left him a note in his faculty mailbox asking him if he'd like to go to the art museum – a daytime get together which could be a date but not necessarily – with my phone no. It worked, we went to the art museum one afternoon and started dating after that.

    Really important! DON'T go straight to the subject of sex!!! Talk about other things. If sex is a possibility it will happen in due time. Even a woman who's ready to jump in bed with you right now wants some lead in time and will be disgusted if you shortcut to the sex part. When your friendship evolves to that point, ask her permission to kiss her or hold her hand.

    I agree that it's strange that you don't want to be seen in public. Do you mean with her? Do you mean just in general? If you're taking a subway I'm assuming you live in a big city, so maybe if you want to be discreet just go somewhere out of the way, plenty of places where you can be anonymous in big cities.

    I think it's always good to at least try for what you want. You might not always get what you want, but at least you tried. I've ended up having some great things happen, not just sexually, because I got courageous and decided to go for it.

  4. Joan Price on October 30, 2009 at 4:20 pm

    Anonymous, I've already written several dating tips posts for younger men — see the label "younger men older women" in the right column or go directly to:

  5. Anonymous on October 30, 2009 at 3:26 pm

    Hi Joan I agree with you about being seen with a older woman,I am in my fortys and I have dated a woman over 65 ,to me it was a honor to be seen with her and I dont care what others think in public but I do care that she felt special when we went out on our date, Joan I would love to see you do a blog on dating tips for younger men in future, thanks Ben

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