Compared to some of your recent correspondents, my problem seems minuscule, but I respect (and urgently need) your advice, so here goes: I am in my early 40s, a "sole father" to a young boy. His mom died about three years ago, of cancer. We had been married 10 years and had a good relationship. I now have a good home and job, make decent money, am in good health, and am reasonably attractive and fit. I live in a city far from any relatives, but I have a decent support system of friends. I have started to get back into the dating scene and am finding it even more confusing and frustrating than the first time around, when I was in my 20s, possibly because the stakes are higher, the pickings are slimmer, and my time is considerably more limited.
I would very much like to get remarried (I'm not much of a "player" and becoming an aging Casanova of the cul-de-sac does not appeal to me.) I try to get out there and meet people and have had some success, although nothing so far has worked out. Getting rejected doesn't bother me (that much), but I find doing the rejecting to be very unpleasant, so much so that it makes me want to quit dating altogether, which I sometimes do for months at a time. So what do I do in the following scenarios:
1. It's a first date, usually coffee or lunch after having been set up by a well-meaning friend or having e-mailed on Match.com. She's nice, but I'm not interested. How do I communicate that without hurting her feelings? Typically I say, "I'll call you," then don't, which of course is a weaselish thing to do.
2. Things have gone well past the first date, and we are into month two or three of the relationship when I realize that she is simply not "the one" and that I am not all that into her. By this point, I have met her friends and possibly her kids, and we have probably had sex. Now what? One of the great things about being married was never having to break up with a woman. Now the prospect of doing so is becoming a real impediment to what little social life I have. Help!
Sleepless in Denver
I picture you, with each woman you date, having a conversation early on in the dating, maybe sitting in your car after a good meal, or maybe right when you first meet, to just lay the ground rules.
It doesn't have to sound cold and doctrinaire, like "Here are the ground rules." Just remind her that it's been three years since your wife died and you're ready to find a new mate, but that you're not particularly comfortable with the process of selection and rejection. Maybe it seems like a cold and impersonal approach to life; if so, tell her that's how you feel. Perhaps you're concerned that, because of your inexperience and your native disinclination for the process (you don't have to use those words!), you may tend to let a relationship continue even though you know it isn't going to lead to marriage. Tell her of that concern -- that if it's comfortable and you like her, and you don't want to hurt her feelings, you may find it hard to break it off. Endings are painful for both parties, no matter who initiates it, so your reluctance should come as no surprise to her, and your honesty about it will probably be welcome.
Then you might ask her what she thinks. First of all, is she truly interested in finding a mate? How would she prefer to end it if it looks like it's not going to lead to a long-term commitment? Maybe she has some thoughts on how you two could get out of this gracefully if either one of you senses that it's not leading where you want it to lead. If she proposes a solution, think it over carefully.
This is a very important little talk, because you're making agreements about delicate things; the danger is that you may make certain promises that you will later regret. For instance, resist the temptation to say something like, "If you find you don't want to continue this, I'll understand; I won't be hurt." Don't say that. Chances are if she breaks it off, you will be hurt, at least a little. In a way, it would be insulting to her if you weren't. And it's possible that you could fall for a woman who has no interest in you. So try not to set traps for yourself. Instead, just look for some kind of mutual understanding about the difficult process you are both undergoing. Look for a way to be graceful but honest.
If it's clear from the minute you meet her that you're not interested, be polite. If there's nothing there, don't shout it out, but don't pretend. Call her after the date and be honest -- tell her you enjoyed meeting her, and you appreciate her going out on a limb to have coffee with a stranger, but you don't think you'd be compatible long-term.
If you are dating someone you like but you're not sure, you might find yourself wishing you could set a firm deadline -- "In one month we will talk" -- but that could put undue pressure on both of you. Better would be to say in general terms that after two or three months you'll probably both know if it has the potential for a lasting relationship, and that you'd like to be ready, at that point, to bring it to a dignified conclusion if necessary.
What's important, it seems to me, is to be realistic but to leave room for the miracle.
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