Category Archives: Dating

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He e-mailed us to say, “I’m dating both of you”

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Cary’s classic column from TUESDAY, JUN 16, 2009

I thought I liked this guy, but his message to me and the other woman he’s dating seemed pretty tacky.


Dear Cary,

I value your advice and read your column all the time. Anyway, after a long hiatus, I dove into the dating pool. I heard that my longtime friend Bob’s cute brother Sam was newly single. I sent him a card telling him that if he’d like to see a movie sometime or have lunch to call/e-mail me. Bob cautioned me that Sam was newly divorced and maybe I shouldn’t take action. I decided to anyway, even though I respect Bob’s opinion about most things.

Anyway, I really fell quickly for Sam. We couldn’t see each other very often because we live two hours apart and as a single parent I could only arrange to see him maybe once a month at most. The few times we saw each other lasted for several hours … we had so much to talk and laugh about — incredible chemistry … and we had frequent e-mails/phone calls in between … it seemed like we had a rare connection, at least to me anyway.

Then, I get an e-mail that he just started seeing someone that lives in his building. Now, get this, he e-mails me and Suzy on the same e-mail at the same time … as in “Margaret and Suzy, I am seeing you both … like you both … want it all out in the open …” I thought this was in really poor taste … didn’t seem to go with the thoughtful person I knew.

Anyway, I tried to be classy because, well, he could have continued seeing both of us and maybe I wouldn’t have found out … so in a weird way, I did appreciate his clumsy honesty. I told him that I couldn’t see him while he was seeing someone else; physically and emotionally I just wasn’t cut out that way and I wished him well.

He has since e-mailed me that I was the most genuine person he has ever met and that his time with me couldn’t be compared, and he signed it “Love, Sam.” Part of me wondered, What the heck does this mean? But the logical side of me decided to just ignore the e-mail.

Not sure if I will ever hear from him again, but I do miss him. If I do hear from him, is he worthy of another chance? I think so, but sometimes I have such huge rose-colored glasses on when it comes to romance that I set myself up to get slam-dunked. And I felt so sad about all of this.

This guy made me wonderful dinners. Made me CDs of my favorite songs. Loved to slow dance … I felt so at ease with him … but since he decided to see someone else I have to wonder if it was all BS.

I hate to think so. What do you think, being a man and all?

Puzzled

Dear Puzzled,

What I think, being a man and all, is that sometimes women spend too much time trying to figure out what we men are up to and not enough time trusting their own judgment. I think you’ve already decided what to do. That e-mail struck you as manipulative and invasive and strange, and it put you off.

Yet you crave his attention. Craving his attention is not a good basis for a relationship. Craving his attention is like needing a drug. He made you a nice dinner. He says nice things to you. Those things — the slow-dancing, the CD, the dinner — those are not the relationship. They are relationship-oriented products. He has shown himself to be an adequate producer of relationship-oriented products. You haven’t really encountered him as a person yet; you’ve only encountered him as a competent dispenser of feeling-like substances.

Not to say that all courtship behavior is a sham. Courtship behavior and its attendant relationship-oriented products make it safe for men and women to dance together. But within the slow dance and the dinner is supposed to be some relating. You have to sense there’s a man you like in there somewhere. I’m not sure you do. I feel more like you were so fragile and hungry that you fell for the appearance of something — for the relationship-oriented products he is able to produce. And that puts you in a dangerous spot because, as you say, you are a person who has such “huge rose-colored glasses on when it comes to romance that I set myself up to get slam-dunked.”

Some people call that “having boundary issues.” Having boundaries is about knowing your weaknesses and protecting yourself.

There’s nothing wrong with feeling fragile and hungry. It happens. We’re in a fragile, hungry time. I suggest, however, that you never allow yourself to become so fragile and hungry that you go against your own core values and instincts.

As a man, I can tell you that sometimes when we want a woman to do something, we produce our best relationship-oriented products and present them to her as if they represented our current feelings toward her. But what they actually represent is how we think we might feel once we get what we want from her. Once we get what we want from her, we might feel like a slow dance, like a diamond, like a rare filet mignon. But in the beginning it’s not poetry; it’s sales. Relationship is knowing and accepting another person. You have to like the guy. He has to not creep you out.

So what do you feel about a person who would send the kind of e-mail he sent? Some people might actually like it. But I think your reaction was like the reaction many women would have, which was that it was just tacky and strange. So trust your own response. I think you’ve already decided what to do.

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Guys keep dumping me

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Cary’s classic column from MONDAY, SEP 3, 2012

We date for six weeks and then they say, “There’s no spark”


Hi Cary,

I enjoy reading your responses because they are honest and very heartfelt, and –  I hope this doesn’t sound over the top — they’re often quite beautiful too.  

I am the (embarrassingly) clichéd successful young woman who is still man-less. I’m 30 years old, I have a wonderful career, numerous close girlfriends, a sometimes frustrating but close and always supportive family, generally great co-workers and acquaintances.  I’m slender, fit, attractive, my nieces and nephews love me and people often call me their sunshine in perhaps an otherwise gray day. A source of pride for me is that I regularly make people laugh. I don’t say these things from a place of arrogance, or at least I hope not, but to set the scene for you, to give you a sense of who is on the other end of this letter. The good parts of me. The parts that everyone else sees.

And yet, I am single. I’m not temporarily, in-between relationships-single, I am chronically, seemingly unstoppably single.  I haven’t had a proper relationship in about four years. The people around me don’t understand why I’m alone either (or at least that’s what they keep telling me), and I trust them to be at least mildly honest about my deficiencies. And believe me, I know I do have them (OK, since I listed my good traits, I’ll list some bad as well — I’m overly sensitive, I’m very particular, I’m stubborn, I’m blunt to a fault at times, I cry every time I get upset, I can be self-obsessed and overly analytical, which is boring for others, etc., etc.).

Don’t get me wrong — I can’t say that I don’t meet men.  I do meet men, I do go out on dates, I do start the very beginnings of relationships. Over and over again. And not with jerks or awful men either — generally pretty decent guys, successful, kind, smart, funny, attractive. Catches. The problem is that after a few dates, they don’t seem to want to continue a relationship with me. About five to six weeks in, around the time things may become exclusive, or at least we start to talk about it, I generally get dumped on my butt or I have to end things because he tells me he’s not looking for anything more than casual. Sometimes I’m dropped in insensitive ways, but usually not — I get the old line that I’m great, he just doesn’t feel a spark. He just doesn’t think that we’re right long-term. There’s just something missing. Then these guys go on to happy relationships with someone else. I am not perfect in a relationship, but I try to treat a partner with respect and kindness. Nobody has ever called me a bitch after we’ve ended things — in fact, I’m still in touch in some form with nearly every man I’ve ever dated and slept with!

I tend to believe that there is a reason for the way things are in our life, and if someone can’t maintain a relationship, there’s a reason for that. If a woman keeps ending up with a guy who treats her awfully, it’s because she’s dating guys who are awful. Of course there’s more to it, but that’s the bare bones.  So, what am I doing wrong? What is the reason that guys want to date me at the beginning, but then lose interest so fast? Do I give a better first impression than the reality? I can’t help but start to develop a complex that, once someone really gets to know me, they are disappointed that the real me isn’t as great as the first-impression me. I would love to believe that they’re “intimidated by my amazingness” as some of my friends say, but let’s get real here — a guy wants to keep amazingness, not throw it away. I’m not completely delusional.  Is it that I’m punching above my weight? Should I pull out some old wives’ trick and try harder to make these guys stay? I’ve always thought that was a bit pathetic and a sure way to a crappy relationship, but maybe it’s in fact what all women do but we just won’t admit it.

There seem to be lots of uninteresting and unattractive (to me) guys out there, so maybe I’m just too picky by only dating the ones that really attract me. When I was 23 I threw away a chance of a baby and marriage because I panicked, I felt too young, completely unprepared and I wanted so much more in my life. I still fiercely respect my right to that decision, but I’ve regretted it for years and now all I want is to be tied down. Is this some kind of karma? My greatest fear is that I’ll be in this same dating Groundhog Day five years from now, so I want to stop the pattern that I’ve created, but I have no idea how.  I’m exhausted, and I want to find a good love.  Please give me a cold dose of reality and help me see this more clearly.

Trapped in Dating-Groundhog-Day

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Dear Trapped,

I am going to go out on a limb here and speak to you as if I knew you, even though I don’t. I am going to speak to you as if I knew your problem, as if it were something like mine.

My guess is that you are not “connecting” because you are not being your authentic self. Now, this is a huge thing to say. It may sound pretty nervy, and I admit it is. But I’m just going to say it.

You are acting in a way that is socially acceptable and no one could fault you for, and yet this way of acting is not right for the real you. In some way, you are being untrue to yourself. This is of course a long life habit, as it is with me. It is a hard habit to break. And it is hard to accept the proposition that while we are not liars or cheats or thieves, we are yet, at some deeper level, being emotionally deceitful. I’m probably going to be accused of “blaming the victim” or something but that is not what I mean.

I know this: People respond to our authentic self. If our authentic self is hidden, then they lose interest. We are of course taught to hide our authentic self. Most of us have an authentic self that is at odds with social expectations, so we learn to suppress it. In rare cases, people we think of as “charismatic” have authentic selves that merge well with the social moment. Such people are lucky and become famous and well-loved. But in your case, and in my case, the authentic self may not be the self you show the world, the successful, cheery self. But it is real. It may shock some people. It may not be welcome everywhere. But it is the real you.

You hint at this when you express the fear that once these guys get to know  the real you they lose interest. I think that is close but not exactly it. When we see a person truly, we cannot help but love her. But when we catch only a glimpse of her hidden self, then we are confused. We sense contradiction and a great hiding, a hiddenness. The “spark” these guys are talking about ignites when the genuine person is seen.

Here is another thought: You may still be mourning the loss you had at 23. I would guess you are still angry and sad about this thing. I feel for you. I am sorry for your loss. You probably put on a happy face and cheer people up but you are not happy. You are still sad about this. You don’t know quite why you did what you did. Perhaps even the burden of choosing was not an unqualified gift. I don’t know. We are complicated. Social and political rights are complicated. We can be grateful for autonomy and yet also yearn to have the path laid out for us. We can relish making our own decisions and yet at times hate the burden this places on us. You made a choice and it was the right choice at the time. You weren’t ready.

One thing that can happen after an event like that is that we go on in a state of incompleteness, of incomplete mourning. This is what people mean sometimes when they say we have “baggage.” We have not moved through certain events emotionally, so we are still responding to current events as though they were happening in the past.
So let us regard this string of unsatisfying encounters as a sign: Your mission is to encounter your authentic self. I wonder who she is.

She may be fierce and angry. She may be wounded. She may be simply sad. Who knows, she might be fiercely funny. She might be frighteningly strong! She may be voracious and sexy and naughty. She may have wanted all her life to be a scientist or mathematician. She may want to be a fisherman. She is probably many things. I wonder who she is. Show her. Let her be. Then she will find her mate.

You have accomplished a lot on the outside. You have some inner work to do now. If you begin this great journey now, no matter what happens in the arena of dating, you will find your authentic self and that is the great human mission.

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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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Help! I’m falling for a fat man!

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Cary’s classic column from THURSDAY, JUL 27, 2006

I like this guy a lot, but the poundage is a turnoff.


Dear Cary,

Currently I’m dating a man who just won’t leave my consciousness, not for a moment. I think of him all the time. He’s pretty special.

My problem is this: This wonderful man with whom I’ve shared some amazing moments and do share a phenomenal connection … he’s overweight. He’s not merely out of shape or a hike and a swim away from fit, he’s fat.

I’ve made a conscious effort to look past it (“it” being my own stupid, shallow, superficial, counterproductive reaction to the weight), but there it is, all of the time. In bed, he’s attentive, very strong, wonderful — we enjoy genuine chemistry — but even when the lights are out I find it difficult to navigate his flesh. I’m a smallish person stature-wise; it’s difficult for me to wind around a man with what little leg I’ve been given, never mind a man the size of one and a half men.

Worse yet is I fear being a selfish lover, because I don’t fantasize pleasing him the way I would ordinarily with a slimmer man. I’m intimidated, daunted and generally unprepared for certain activities.

I don’t know what to do. It’s a turnoff. And worst of all, part of the reason it’s a turnoff is that I see myself with a head-turner when the lights are on. I’ve always been with striking men — not pretty boys, but men who had that quality; after all, it’s that quality which turns my head in the first place. And this man just doesn’t light my fire in that way. I’m attracted to nearly everything about him but his size. So he doesn’t light my fire, and doesn’t feed my ego in the company of strangers. I hate myself even for admitting it; it’s just so superficial.

Am I trying to convince myself that we have a future together? Is there any way I can get past my bias and enjoy this person for who he is in total?

Weighing in, in Washington

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Dear Weighing in,

You haven’t gotten this far by pretending. You’ve gotten this far by being straightforward and honest, and I suggest you continue being straightforward and honest.

This is harder, of course, because we are freaked out about fat. It is one of our crazy things. It goes deep. It has its paradoxes and corollaries as well — we are freaked out about skinny, and we are freaked out about food, and the planet, and the body and money and exercise and power. We are a freaked-out culture. We are all freaked out.

The fat man knows this.

If you are a fat man in America you cannot help noticing that people are freaked out about fat. People will suggest exercise bikes. They will feed you lean portions. They will say to each other, “It’s his fault, and it’s disgusting; he must have no willpower; he must eat the wrong things; he must be repressing something; he must not respect himself.” And what does the fat guy say? He says, Yes, thank you for that astute observation, I have indeed noticed that I am fat.

So I suggest what you do is go in your backyard and sit quietly and meditate on the fact that you are not turned on by this fat man. Meditate on the fact that you like him very much but he doesn’t turn you on. Wait for something to come to you. Accept the answer that comes. If you come to the feeling that you have to end it, then end it. If you come to the feeling that you want to stay with him for a while more, then stay with him for a while more. If you come to both, then put each on an apothecary’s scale, weigh them and choose the one that weighs a little more.

Don’t try to reason it out and don’t guilt-trip yourself. We don’t know why we are the way we are. It’s not our job to know. Just meditate on it and wait for an answer.

Maybe you meditate on it and the answer that comes is that it’s just not right for you. OK. Make a tearful goodbye. Or maybe you meditate on it and it continues to intrigue you and so you stay with him for a while. What’s the harm in that? Maybe you learn something new. Maybe you have sex and it turns out to be good. Maybe it’s just some learning you have to do — maybe you are not used to having sex in ways that are not automatic; maybe there would be some learning at first and then it would be automatic, just as it always was. What can it hurt to find out?

And by the way, why are you in such a hurry lately? Two or three dates is not all that much time. Human emotion goes slowly. Insight is a complex computation; it can take days on our little computers.

Besides, consider: The sex is great in the beginning lots of times. This you no doubt know. It doesn’t always stay great. It might dwindle down. It might be great at first with some guy you don’t like that much otherwise. It might dwindle down and then what have you got? A guy you don’t like all that much anyway whom you don’t like to fuck much either anymore.

Some things are painful and sad and wrong but nonetheless true.

We are the way we are for reasons unknown to us. You needn’t feel guilty if it isn’t working out. Quiet your mind and wait for the answer to come to you.

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My new boyfriend’s mom has cancer

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Hi Cary,

I am seeing a great guy, but things have recently become very ambiguous between us and I’m not sure the best course of action for me.

We were dating for a little over two months, it was a slowly deepening fantastic and mature relationship, and I care for him, he clearly cares for me, we were falling in love. But as it happened, on our second date he found out his mom has a widespread and fast moving cancer with unknown prospects for treatment.

He didn’t seem much affected by it at first, and he consistently deflected my offers of support and my concern. But over the weeks I felt like he was holding back, being emotionally distant, reluctant to fall for me, and eventually started contacting me less and being less available to see me.

I asked him about it, and he came back and said that due to his mother’s illness something fell apart in him and he can’t manage to be in a relationship right now, that things were great with me and it isn’t me, but he can’t tolerate the contrasting pleasure and pain, he can’t be there for me, he can’t uphold his end of a relationship, and he doesn’t want to hurt me or let me down, that he has to do this alone, that it’s simpler and a relationship would complicate things. He didn’t say the words break-up or just-be-friends, but he made it clear we are no longer in a relationship. Since three weeks we are still in almost daily contact and see each other around once a week, we have joint projects and plans to do things together, he’s still affectionate. Last time I saw him we were overwhelmed by our mutual attraction and made love all night, but in the morning he was distant and bothered by my presence. His behavior is quite clear that it’s no longer a relationship, but something else and rather ambiguous.

We have both handled this situation quite delicately, thoughtfully, and I want to be there for him as much as he will accept me, as much as he needs, but I feel tortured and confused about what that means for us. We have feelings for each other, we are attracted to each other, we enjoy each other’s company, we have joint projects together… but he isn’t available for a relationship.

How can I find a way for me to continue to be there for him without torturing myself always pining for more, how can I find a peaceful sustainable existence in this ambiguity? How can I ride this out with him, deepening our connection, our intimacy, and be there in the months or years when he is ready for a serious relationship? How can I give my support and love, but not expect him to reciprocate ? Should I invest myself in my single non-romantic life? Should I move on and date other people ?

Thanks for your help :)

G

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Dear G,

Just tell him, clearly and often, that you are there for him during this time and that he does not need to right the balance sheet. There is no balance sheet. There is just you. You are there for him and that’s the end of it. That’s what he needs and it’s what you can give him.

You say you feel tortured and confused about what this means for you. It’s not surprising that you’re confused. One set of rituals has collided with another.

But there is no mystery about what is required. What is required is that you behave like a good, caring human being. If you make love you make love. If you don’t talk for a while you don’t talk for a while. The rules of romance are suspended. If you have needs for companionship or sex that he cannot meet, do not feel bad about meeting them in other ways. Being there for him doesn’t mean you put your life on hold. Just be there for him when you can be. Contact him regularly and don’t require him to call you back. Just remind him regularly that you are there.

Relationships deepen when one partner suffers a loss. In unguarded moments your friend will reveal hidden strengths and weaknesses. His core beliefs will come to the fore. You will see who he is.

It’s possible that you will be surprised by what you see. It’s possible, likewise, that he may not be able to be intimate with you in any meaningful way while he is facing the possible loss of his mother.

What I meant when I said that two sets of rituals had collided is that the ritual of dating has collided with the ritual of friendship. The confusion that results shows just how artificial the expectations of the dating relationship are. It seems to presume that no unforeseen human events will occur. When they do occur, the dating ritual participants are thrown into indecision.

This illustrates how dating rituals distort our natural instincts toward compassion and caring. It’s very interesting: If he were a friend, even a friend you’ve only just met, you would not be confused about how to respond to this event in his life. You would express your concern and make yourself available to him. But because you are following a dating ritual, each of you feels strangely compelled to apologize for the disruption.  It is as though people date in a vacuum, excluding all real-life events.

So the important thing is to act in the human sphere, to act in friendship. Put “the relationship” on hold.

Let go of your hopes and expectations for a relationship and just be there. Be a good human being and a good friend. You know how to do that.

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Doctor in love

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Cary’s classic column Tuesday,  NOV 4, 2003 10:29 AM PST

I had a crush on a colleague, and now she wants to be friends, but I don’t. How do I get rid of her?


Dear Cary,

I’m a Salon reader from Mexico and I enjoy reading your column very much. Now I need your advice.

I am a medical doctor and there is a colleague of mine I had a big crush on, but circumstances have not been appropriate for me to try to “advance” the relationship (she had a boyfriend at first, then she was out of the country for some time).

When I finally started — rather softly — to make a move, she started working with another doctor, 10 years her senior. Obviously he snatched her. Now, I am not really hurt nor do I have any remorse or hatred. It was just a crush. I was not in love or anything. It was not meant to be, and I am over it already. But she wants to keep being my friend. She seems to be completely clueless about my feelings. I don’t want to keep being her friend. I don’t loathe her; I just don’t want to be around her anymore. But I don’t want to hurt her. I don’t want to face her because I know I would end up saying more things than I would rationally think convenient.

I have tried to be evasive, tried to drive her away in a “passive way.” But she is still there. What should I do? How do I get rid of her (in a smooth way)?

Tired of Being Nice

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Dear Tired,

When beings are denied privileges solely because of attributes over which they have no control, such as whether they are women or men, or white or black, or human or animal, it is sometimes called “objectification.” What that means, I think, is that the one who has the power is free to act as though no bona fide relationship exists with the other, as though there is no bond of reciprocity, as though the other were a piece of furniture or a magazine, to be used without regard for its feelings or mental processes.

That sort of objectification is what your letter hints at, and it is that habit of being that you need to address. The tragedy of such a habit is that it walls off a rich and rewarding realm of human bonds, in which we trade some of our power and autonomy for a sense of community and trust.

“Obviously he snatched her,” you say. That makes it sound as though women are routinely handed around from doctor to doctor like so many copies of Playboy, to be privately enjoyed and then passed on. If so, there is a certain ethical inequality in your workplace, a kind of gender discrimination. I’m not saying it’s the kind of thing you can fix, but it’s the kind of thing you, as a doctor, should recognize as poison and avoid in your personal dealings.

I think you really did have feelings for her. You say you were not hurt, that it was just a crush. Regardless, you do not have the right to smooth this over and make it go away just because it is inconvenient for you.

You have probably spent most of your youth studying the medical sciences, looking for ways to control disease and analyze chemical and biological processes. So you may not have had much time to study how human communities function. But I think you will be much happier in life once you understand this: You have entered into a relationship with this woman already. In a moral sense, you do not have the right to simply, “in a smooth way,” get rid of her. You owe her the truth: That you were interested in her not as a friend but as an amorous companion, and now that the possibility of such a relationship seems remote, you are disappointed and it is painful to be around her.

What she then does with this truth is her concern, not yours. The reason we tell each other the truth is that we want to maximize personal freedom: The more truth someone knows, the better she can make the best decisions for herself. It’s true in medicine, and it’s true in relationships.

If it helps in preparing your speech, conceptualize it this way: You have some bad news to deliver to her. Deliver it like a doctor. Tell her the facts. Tell her what her likelihood of recovery is and explain her treatment options. Tell her the condition is curable and not fatal.

But please do not tell her that simply because it sounds good. Tell her the truth. And if you should say more things than you would “rationally think convenient,” there’s no shame in that. There’s no shame in having strong feelings for someone, or in feeling disappointed or spurned. It’s part of being a man.

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He’s sober but he steals hotel towels!

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Cary,

I’m dating a man but I’m uncomfortable with some of his behaviors. He is about eight years sober and attends Alcoholics Anonymous regularly. He and I dated about four years ago and I adored him but couldn’t tolerate some of his bad behavior so the relationship ended. He seems to have grown a lot in the last four years and I was excited and hopeful to give the relationship another chance.

However, he still doesn’t follow the same rules of society that I do. Here are some examples of things he’s done in the last couple of months: He’s tried to sneak into places that he should be paying to enter; he’s takes the towels from hotel rooms; and he outright lifted a towel off of the maintenance cart and took it home.

He knows I’m uncomfortable with his behavior. He jokingly asked if I would feel better if he returned the towels to the hotels (and I said yes).

He occasionally will tell me things he did before he was sober. For example, he said he flooded a vacant house on purpose. I hear no remorse from him when he tells these stories and it seems unlikely to me that he ever worked the Step 8 the way it was intended to be worked.

When I reentered a relationship with him this time I went in with the attitude of keeping things light and taking things day by day. But now he is asking more of me and I’m losing interest in him.

I don’t know if I should just ease out of the relationship or if I should let him know why I’m cooling off. It seems only fair to tell him why I’m backing away, but I don’t want to create a scene either. I would want to stay in the relationship if he was working on changing this behavior but I know I can’t change him.

Your advice sure would be appreciated.

Sunshine

Cary Tennis Writing Retreat in France

Dear Sunshine,

You can’t change him. But you can place before him the opportunity to keep going out with you, and let him choose. You can say to him, I like you a lot but I won’t go out with you if you keep stealing towels.

Then it’s up to him. I’d choose you over hotel towels and I don’t even know you that well. But you’ll just have to find out what he wants to do.

Maybe he has a different definition of stealing. When people are drinking sometimes they have a different definition of drinking. Like beer is not drinking. Or one glass of wine is not drinking. So maybe to him taking a towel is not stealing. Maybe it would have to be fifty towels for it to be stealing.

If there is a definitional problem at the heart of this, Webster’s Third New International Dictionary, Unabridged, may help.

I get what you mean when you say you can’t control his behavior. You’re powerless over that. But he’s not. He is capable of making choices. So put the choice before him. He may be motivated to change his behavior when he contemplates the benefits to be obtained.

There is, of course, an apparent contradiction between his attendance at AA meetings and his attitude toward stealing towels and sneaking in places. Maybe he hasn’t read the AA literature on stealing towels and sneaking in to places. (Just kidding. I don’t think the literature expressly contemplates such activity; one is left to make such connections on one’s own.)

But let’s not go there. His membership in AA is his business. The thing that properly concerns you—and it is a proper concern—is that he acts dishonestly in front of you. That troubles you. It should. So just tell him it’s a deal breaker. And then stick to it.

Now, you’re not his AA sponsor, and neither am I, and it’s none of our business, but I am a writer and writers are curious and like to create hypothetical scenarios for sheer amusement. So personally I would find it amusing if, say, his sponsor were to recommend that he take a rigorous textile inventory of himself.

Or of his house. How many towels has he got in there? And how could he make amends? Should he visit each hotel and walk around the halls until he finds a housekeeping team hard at work, and just casually throw in the towel? (Speaking of which, maybe his resistance has to do with a resistance to surrender, i.e., he refuses to throw in the towel.) (Groan.)

Anyway, I like the comic possibilities. It could be his quest. Like “My Name is Earl.” You could film it and put it on YouTube.

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How do I show her I’m serious?

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Dear Cary,

I have been reading your column, particularly your relationship advice for so long that sometimes the stories mirror my own hopelessly romantic life with such accuracy I’m convinced a significant other wrote it. Thank you for sharing your insight in these instances;  I can rest a little easier knowing I’m not alone in my quest to understand the complexities of relationships and the abundance of feelings that come with it .

I’d like to take the moment to tell you a story. There’s a woman I’ve known for some time. A few months ago I decided to pull the trigger and be more than friends with her. She is everything that I would look for in a long-term relationship: intelligent, success-driven, affectionate and genuine about her feelings. We connect on many levels, share many similar interests and aspire to the same goals. When we’re together, I feel like the luckiest guy on earth.

But that’s not to say it’s all perfect. There is also a side of her often leaves me anxious and frustrated. I’m no angel and being friends for so long, she’s well aware of my past misgivings. Her trust issues and insecurities over my willingness to commit to one woman have put me in a limbo between just dating and a committed relationship. The other “main” reasons she gives are: not knowing exactly what she wants in the long run, a former love interest she can’t seem to get over and her fear of falling in love and experiencing heartbreak again.

This has led me to wild emotional goose chase to prove myself to her. I have repeatedly attempted to put her fears to rest. I’ve told her my intentions, opened myself honestly to her questions about my past and have been patient through it all. Still, no dice. Her insecurities have damaged some of my friendships and are constantly putting a strain on our relationship.  Combined with her family’s constant involvement (they actually love me, which makes her even more anxious), I’m beginning to doubt if this is what I want.

Cary, what should I do? I’m in no rush to settle, but there is a strong desire for some stability at this point in my life. I genuinely like her and I might even be in love with her (that’s a whole other story). How do I explain that holding off on me while holding unto the past only makes me more apprehensive about our future? How else can I show her I’m “for real, for real” about what we have? How can I get her to let me in and trust me just enough to continue to grow and build our relationship? Or should I just move on? I feel that taking a laid-back approach forces me to just settle with whatever I’m given, and for me that’s a deal breaker. I’d hate to walk away from it all, but I’d even more hate to know I’m wasting my time.

In Limbo

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Dear In Limbo,

The traditional—and quite effective—solution to the kind of limbo you describe is to ask her to marry you.

That is how you say you’re for real for real, you’re in it for the long haul, you’re not the man you used to be. That is how you say you’re not kidding around and you’re willing to risk not only that unendurable moment after you ask her when she sits back in her chair and gets a cloudy look in her eyes and the thought crosses your mind that she’s about to say no and you’re about to be humiliated, but also the following however many umpteen millions of years that represent the rest of your life.

It’s also how you get her to let you in and trust you enough to continue and grow and build the relationship. You may be thinking that if the relationship would only grow and build then you would be ready for commitment. But it’s the other way around. The relationship grows and builds because you make the conscious choice of commitment. Trust develops because you consciously create the conditions for trust. You don’t wait for the relationship to build. You build it.

Asking her to marry you is also a test for you. If you find that you’re not willing to ask her to marry you, it means she’s not crazy for having her doubts. Certainty doesn’t always come. You have to live with uncertainty and risk something dear to you. You have to take a chance.

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I’m dating my doppelganger

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Dear Cary,

About seven months ago, I was coming out of a really bad relationship with a younger guy who was an immature, boring freeloader. He also cheated on me with men and women, indiscriminately. As long as he was receiving attention, he was happy. After breaking up with him, it was apparent he had mental issues; he threatened to sue me, and kill himself on my property. The cops and his parents had to remove him at various times from my porch.

During this time, I had friends and coworkers trying to introduce me to someone in particular, who they touted as “the male version of me.” Amused, I asked why they thought that and was told we looked, dressed and acted alike, and people wanted to see if we were long lost relatives. I don’t like being part of a spectacle so I ignored requests to meet this person. Then, I ran into him on my own outside of work and it was like looking into a mirror. I think we were both transfixed at how uncanny the resemblance was. Upon just meeting he even quoted a geeky joke that I knew the obscure punchline to.

I’ve never believed in soul mates or kinships before but I felt we had some kind of weird connection. I didn’t think it was attraction at first. We discovered we worked at the same place, and then it occurred to me, this was the guy my coworkers wanted me to meet. We became fast friends, hanging out at every break and day off. Due to the problems with harassment I was experiencing with my ex, I was disinclined to get into a relationship, so I never made any kind of flirtatious overtures. Meanwhile our mutual friends were encouraging us to date since we had apparent chemistry. I was happy to discover he had a girlfriend already, at first because I thought it would relieve my guilt at friend-zoning him, but later I realized I was just happy that it was a sign he wasn’t gay and therefore fair game.

When I met his girlfriend, I actually liked her. I still would but it would be awkward to befriend your lover’s ex, that he dumped for you. Yep, you read that right. It is exactly what happened. Our mutual attraction, physically, intellectually, emotionally, and the urging of our common friends eventually chipped away at their relationship, and shortly thereafter we began dating. I have apologized to him about stealing him from her before. He gives me a quirky smile and says if they were as perfect for each other as we are, I wouldn’t have been able to, and that she was “getting on his nerves anyway.” His friends even stated that she wasn’t right for him. They also adore me, and I them. He doesn’t cheat, or hide things or act shady. He’s very honest and open about things. Despite that, I, a little insecurely, wonder if he could be stolen as easily from ME. It would only serve me right.

We seem perfect though. We look adorable together, the sex is great, we share hobbies and interests. We are a complement to each other in some ways, and a perfect match in others, and enigmatic and interesting in still others! We want a future. We’ve only been dating for six months now, but he talks about marriage and kids and our goals and careers with me. We never fight. When we disagree or do something accidentally hurtful, We actually TALK about it maturely! I don’t have a single ex who would have. We can take comfort or cry on each other’s shoulders if we’ve had a bad day or rough life. We do nice things for each other that I imagine partners in a marriage would! In fact, just realizing how perfect he is lately, has made me feel even more remorseful for poaching. How could she stand to lose someone as great as him?

Should I just accept that we are possibly soul mates and they weren’t? As hurtful as it must have been to her for us to date, do you think maybe he wasn’t right for her either and hopefully she is okay?

Do I need more closure to forgive myself? Should I apologize to her if I feel it is owed? I don’t want to rock this boat, but I’ve never done anything potentially this hurtful before and the guilt does eat at me. I actually looked at her Facebook twice to see if she’s gotten a new partner. I really hope she does so she can be this happy too, and I will feel less burdened with taking her happiness away.

Sincerely,

So Happy & I Hate Myself For It

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Dear So Happy & Hating Yourself,

You’ve come a long way since dating a guy who had to be removed from your porch.

In fact, you sound like you are in heaven. Wow.

So why feel guilty now? A better match was made. One is tempted to thank the benign forces of nature. One is also tempted to think well, once in a million whiles the random forces of our chaotic and meaningless universe get something right.

Either way, you’re swell. Peaches. Sweet.

It’s even nice that you feel bad for the girlfriend he dumped for you. You can afford to feel bad for others now because you are so happy.

Life will hit you hard eventually. There’s no reason to hurry that along. If I were you I would keep a journal so you can look back on this happy time. And, while writing the journal, if I were you (and I wish I could be) I would pay special attention to all the reasons, the concrete and perhaps repeatable reasons, that you are happy today. Some of them won’t be repeatable: your youth is not recoverable once it is gone, nor is your relatively undamaged psyche: once life in a declining stronghold of deranged capitalists and war mongers has had its way with you for a couple of decades, you’ll be suitably beaten down and morose like the rest of us.

But certain things you are doing now may be repeatable, and are worth writing down now so you can remember them. For instance: the nice things you do for each other; the way you regard each other; these may be repeatable. So when you get into trouble in the future, when life seems pale and lifeless, when this person you now love so madly turns into an ogre, you can try to recapture this happiness by repeating, consciously, the happy behaviors in which you now engage with blissful, unconscious ease. Remember this. This is sweet. This is how life is supposed to be.

I’m just kind of bowled over. I’m going to enjoy this. I suggest you do the same. Let’s all enjoy this, as a matter of fact, all our readers, everybody. Let’s just let this moment of happiness radiate outward from here.

Don’t mess with a good thing. Enjoy it.

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Am I being used?

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Dear Cary:

Thank you for bringing humaneness to advice columns. I hope you’ll consider taking time to help me figure out a problem. I was raised in a tribal culture where women keep things to themselves in order to keep others from worrying. I have trouble speaking to friends back home to help me work this out, and I am in a very rural area with no therapists close by.

I do not have any friends where I am living.

In 2010 I started doing dissertation research in a small community far from my home. I met a man who was 62. I was 33. He seemed very young, was outdoorsy, and we spent a lot of time together on my project. He has been married and divorced four times. Only one of the marriages lasted a while, with “Sherry” (nineteen years). I have been married once (together for about twelve years, married for five)–the ex had an affair, and I will admit I have trust issues. My ex and I raised his son together, and I promised the son to love him like my own no matter what, and I do. Stepson still lives close to my “home”–far from the research community.

This older man and I started dating as a fling. We discussed that I was going to leave, write my dissertation, and seek an academic job. I’m of mixed heritage — American Indian, black, and white —  and I’m the first on my mom’s side of the family to have a doctorate, so this was a big deal, not just to me, but to my parents and Indian community. I actually did leave the research community and drove back home, to work and write my dissertation. However, a couple days after I left, a mutual friend called to say Manfriend had a heart attack and was in ICU. I immediately went back to take care of him and ended up moving in. His health generally declined from another condition, although he hides it well. He is now on disability, but it is not enough to support him at the level he likes.

Somehow helping him stretched out to three years. I love Manfriend — by which I think I mean I could not stand for him to be alone and killing himself trying to work, which is what he would do if it weren’t for my income.  I have supported him, cared for him, taken him to the hospital and to traditional healers, worried over him, taken care of all the work he can’t do around the house, advocated for him with doctors, etc. His kids rarely visit. He says he loves me, but he does not want to get married.  I did finish writing my dissertation, very slowly, while working two jobs to support both of us. There are no academic jobs here. I do other work in a high-stress but boring profession that does not pay well here.

Here are the hangups. He calls me “Sherry” sometimes. He speaks about Sherry to others and tells them how pretty she is, even shows off pictures of her and their daughter together and refers to her as “my old lady.”  Manfriend comments about how other men who are “shacked up” with women do so because they do not respect their girlfriends enough to marry them. About two years ago, Manfriend made comments about wanting oral sex from another woman in front of me and whispered to her something apparently salacious in front of me. He has not taken me out in about a year, so I no longer see him interact with other women, although he claims that the hitting on the other woman was only when we were “not as committed” (we had been living together and I was supporting him even then). He tells me that he thinks it is funny to tell people in town who ask about me and him (it’s a small town, and the age difference as well as my profession and race make us a curiosity for gossips) that he doesn’t even know me.

Manfriend is not as bad a boyfriend as it might sound. What I haven’t said is that he is also kind when he’s not being disrespectful. He cooks for me, listens to my frustrations with my job and my worries about Stepson and my elderly grandfather, and is very affectionate. When we are OK we laugh a lot together. We never go out together anymore. He does go out when I’m at work. By the time I get home and on the weekends, he says he is too tired or that I am too insecure and will get mad at him for looking at other women. But he doesn’t want me to go out by myself, so I have made no friends here other than “work friends,” not people I would share personal issues with.

I know I’m insecure and bringing my own old issues with trust into things. But I can’t get over the feeling that despite all this if Manfriend respected me or were committed to me much he would never have hit on other women (especially not in front of me), could manage not to call me Sherry during intimate moments, and could stop bragging about Sherry to other people. They’ve been divorced 15 years but apparently, according to her religious beliefs, she and he are still married since she does not believe in divorce. I also tend to think he would want to get married since, according to him, not getting married is a sign of disrespect. That we are racially different does not help. Sometimes I really think that if I were white he would not act like he was ashamed of living with me or try to shame me.

This is all very far from my family, and I’m now 36–getting old if I did want to settle down and have a child other than Stepson. I’m terrified that I’m losing precious time with my parents, elderly grandfather, and stepson and obviously weakening my relationships with all of them because we rarely see one another, and that I gave my beloved and also now elderly dogs back to Exhusband (Manfriend is violently allergic), all to be with a man who I sometimes suspect is using me. But, again, I hate the thought of leaving him alone, or of not having him in my life, and I think I find satisfaction in caring for someone.

How do I make a decision I can live with or let wanting a more stable relationship go? We are wearing each other out fighting. When we argue that pain and humiliation of him hitting on that other woman in front of me and telling people he lived by himself and didn’t know me just bubbles up as if they were new. I want to talk about it, and he doesn’t, which means I usually unload it all it once when I figure we’re already in for an argument–not good for either of us–and he responds with sarcasm and exaggeration, which tends to make it hard for me to keep “fighting fair.” The last fight ended with me vomiting up all these worries, crying, and telling him I was scared and him telling me I was making him sick with my “tantrum,” so I’m sleeping at my office for a while.

Any advice would be very appreciated.

Best,

Not Sure if I’m Being Used or Just Poisoning My Relationship With My Old Issues

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Dear Longest Pseudonym Ever in the History of this Advice Column and that Means 12 Years,

Thank you for your letter. I don’t think it’s helpful to simply say you’re being used. It’s more complicated than that.

You are in an unusual relationship. You get a lot from this relationship. You also give a lot. You sacrifice. It is an unequal relationship. But you are not powerless in it. You have some power that you are not using. You have the power of refusal and of withholding. I don’t mean withholding sex. I mean withholding yourself, and the things you do for him.

Rather than be doctrinaire, strategically cut back. Stop doing certain things for him, while still maintaining the essential bond between you. The services you provide are not just practical. They are emotional. You supply him with approval and esteem; you allow him to believe that he is king. It’s OK for him to be king some of the time. But he is not all-powerful. He needs to know that his powers are limited.

I think you’re smart and compassionate and deserving of more than this man is giving you, but it is your responsibility to even things out with him. So pull back. Let him see that he can’t just get whatever he wants from you whenever he wants it. Retire into yourself a bit. Let him feel some tension. Let him wonder. Let him see that his lack of respect has consequences.

You say you are living in a small community far from home. You are isolated. You depend on this man more than you would if you had friends to confide in. So you need to make some friends. If that means breaking certain customs, by confiding things that in your tribe generally are not confided, and by on occasion denying him the pleasure of your company while you go and be among people in more equitable power relationships, so be it. In other words, branch out. Find some friends.

As to the essential question of whether to leave him in order to find a man to have a child with, that is a deep, challenging and far-reaching question I can’t presume to answer. But I do know that though you feel responsible for this man, you are not ultimately responsible for him. If you leave him, he will be OK. He will survive.

I sense that there is something deep between you and him. It is clouded and sullied by his crude lapses. That is a shame. I sense that he is not crude morally necessarily; he is a man of a certain time and he is used to getting away with certain things with women. But it is not too much to ask that he not call you Sherry, and not make crude comments to other women. It doesn’t matter whether you are there to hear it or not. You should insist that he not do this. It is disrespectful to women everywhere. It is wrong. He should be chastised when he does this.

We have a long way to go in this culture; our history of violence and subjection of peoples echoes in the present. To be a woman, an African-American and an Indian is to be thrice blessed and thrice cursed. Most blessings are also curses. This is nothing new.

So go inside yourself and be strong inside yourself. Do not give yourself away to him so freely. Let him see what he has to do. Let him see if he can make it up to you for his crude lapses, his arrogance, his pomposity. You obviously are drawn to a deeper side of him. He is not just an arrogant, pompous man. He is someone you love.

Just don’t be a sucker. Be strong. Make him work for it.

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