Dating rules

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Cary’s classic column from

Is it possible to go out with two women at the same time and get away with it?


Dear Cary,

I’m in a bind: After going a couple of years without a serious relationship, I recently met two very cool women in the course of two days. Gal No. 1 is smart, funny, confident, good-looking and slightly counterculture. Gal No. 2 is smart, witty, lighthearted, self-deprecating and a little bit kooky. On a shallow level, I find No. 1 just a little bit more physically attractive.

As I met them at essentially the same time, I thought it would be OK to get to know them both. I had enjoyable e-mail and then phone relationships, and then had very nice dinners with each. No. 1 is open but taking it as it comes; No. 2 seems to be more proactively interested in me. I might be a slightly better personality match with No. 2, but I really don’t know either one of them well enough to say that with conviction.

In the event that everything continues to proceed well, is there any general time limit or number of dates by which I should get on the stick and make a decision? I’m not the kind of guy who feels OK about simultaneously dating two women, and the last thing I want to do is hurt someone’s feelings. Is it totally stupid to be swayed by the attractiveness of No. 1 even though No. 2 and I get on very well? I’m in my early 40s (as are both women) but feel like a dumb, naive high school kid. I don’t want to screw this up. Help!

Conflicted

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Dear Conflicted,

Does God exist? If God does not exist, then this is random nature at work, which means that randomness can be as kind as it can be cruel, which means that consciousness has no monopoly on agape. I see no reason why you should feel compelled to tamper with nature. On the other hand, if God does exist, then God has put these two women into your life for some unseen but no doubt lofty purpose — not the least of which might be the beneficial effects of certain fantastic imaginings that may occur to you. God, if he exists, is not altogether without a sense of humor.

So what to do? Do whatever you feel like doing. Leave it up to the women. Don’t try to control everything or be super cagey about it. Just lay it out there. Say that you met two women at the same time and you’re currently dating both of them. Say that such a situation has never happened to you before, and you don’t know where it’s going to lead and you don’t want to do anything rash, dishonest or hurtful, so you’re just laying it out there.

I don’t think that you have any great responsibility beyond just saying what’s going on. In fact, I would hesitate to try to spin it in any particular direction, because that could backfire; the minute you start trying to spin, you enter the realm of unintended consequences. You really have no way of knowing how it’s going to end up.

But if the totally Zen approach is a little much, and you’d feel better guiding the conversation toward some definable options, you might ask each woman if she has entertained any notions of your relationship becoming serious enough to warrant the easing out of the other. In other words, try to find out if either of these women is thinking seriously about you.

You might also remind these women that you are a man, and thus completely without guile or cleverness, and that if they think you’re cooking this up as some kind of manipulation, they vastly overestimate you. Remind them that you don’t particularly relish the difficulties it poses.

I don’t think you have much to lose by being open about the situation. I do not think that either woman will refuse to see you on account of it, although if one does, it probably means that she wasn’t all that into you anyway. If that happens, consider yourself to have been granted a second piece of good fortune: It relieves you not only of the burden of a difficult choice, but of the potential heartache of a futile courtship.

So, again, I say, just let go of the outcome and explain the situation. Nothing bad can come of it.

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