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!



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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6 thoughts on “Dating rules”

  1. 2 things going on here: a desire for intimacy (woman A or B), and a desire for freedom (woman A and woman B). You can’t do both.
    This is a big problem: if you dispense with freedom for the sake of intimacy, then ultimately you suffocate; if you dispense with intimacy for the sake of freedom, then freedom becomes a compulsion, a prison.
    If he tells both, they’ll both likely dump him; if they don’t both dump him, he will long for the one who dumped him and grow tired of the one who didn’t.
    My advice: go on a date with each, and really pay attention. Take in as much as you can, as though you were never going to see them again. Then go on hiatus for 2 weeks. At the end of the 2 weeks, what is remembered can be compared: is one faded into abstraction, while the other remains vivid? This might be useful in deciding. Then decide.
    This reads like a rabbi joke, but it’s what I’ve got.

  2. Yep, I’m totally with Cary on this one. Just be honest. There is no need to attempt to be exlusive with someone you just met. And really, it would be pretty foolish to do that during the discovery period. He wouldn’t have to tell either of them that he was seeing one other person, but just say that he’s “dating around” for now.

  3. I agree with Cary’s advice, which is essentially to open up the topic for discussion with parties involved and see if everyone is comfortable to continue without exclusivity, at least for awhile longer. Lots of people are into “open relationships” and rather than close it off prematurarely and trying to mind read, I agree with Cary that it’s okay to just ask for what he wants. Who knows, maybe the women are simultaneously dating others too.

    By being direct and honest, the women have an opportunity to say no or offer other terms. The key piece of advice here was to not try to control the situation and not be cagey about it. That is, to let each person speak for themself and their own needs. I agree!

  4. Cary! This is really bad advice, and beneath you, too, to advise saying ‘I am a man, and therefore completely without guise or manipulation.’ Machiavelli was a man. The most guileful manipulative people I’ve met have been men, and that’s probably because I’m a woman and have been a target of their seductions. So – that aside, what else do I disagree with about your – usually great – advice today?
    Saying that if a woman backs out because she doesn’t want to be dating a guy who is dating someone else she probably cares less about you. I would say just the opposite. It may show she cares a lot about you. Personally, I don’t bother with people I don’t care about. I wouldn’t be emailing and phoning and dating someone I wasn’t interested in. How interested, I couldn’t say, but to be up for all that is already pretty interested. And I would hate to feel as if I was competing with someone. I think that would pretty quickly screw it up for me. And it would be great if everyone could be cool and non jealous and fearful and possessive and controlling, right? But this is about sex and love and all that primal stuff, and dealing with a potential rival can bring out the worst in people, that might otherwise have never even been aroused.
    So, my advise to this guy would be to make your choice. Just do it. Go with number one, probably- she’s obviously the one you like more. Talk to number one, say you’re seeing someone else too but would like to be exclusive, if she would like to be. IF she would, then great. If she wouldn’t, then that’s pretty much an answer for you, right there. Then, be really nice and respectful and great with woman number 2 and say how much you’ve enjoyed getting to know her, but that you’ve decided to be exclusive with someone and so it won’t go any further. This will hurt a bit, but not that much if you do it quickly and honestly. Then, if things don’t work out with number one, which I think they probably won’t, as even in your description of her it sounds as if she is less attainable and therefore pressing your ‘chase’ button (never a good button to run your life on) you can get back in touch with number two and say it didn’t work out, and I’ve been thinking of you, and missing you, and wondered if you’d like to take up where we left off. That’s my advice.

    1. I agree with LauraBB. Telling both women sets up a potentially hurtful competition. In that situation the more I liked the man the more likely I would be to immediately stop seeing him. Whereas, if I cared less and just felt it was a fun fling, I’d tend to not care if he was dating someone else.

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