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.