Category Archives: Dating

Am I fickle?

Cary’s classic column from WEDNESDAY, MAR 5, 2003

I am exhilarated by the chase, but once I catch the girl I lose interest.


Dear Cary,

I’ve realized slowly over the last few months that I am one of those guys who is exhilarated by the chase but disappointed by the prize. My relationships never last for more than a few months because I lose interest in the poor girls so quickly once they’ve been “caught.” It has gotten to the point where I am sometimes glad when my pursuit of a girl does not work out because I can still care for and about her. I’ve pressed the pause button on anything that has the potential to become a romantic relationship for now because I’m worried about what this says about me. I’ve just gotten out of college and looking back this has been a pretty rigid pattern for me. Is this something I can expect to grow out of? I don’t know what to do aside from acknowledging that there is a problem.

Young and Fickle

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Dear Young and Fickle,

Yes, I think you will probably grow out of this. Or, more accurately, your social life and your work life will solidify, and the networks of people you associate with will grow more regular. As that happens, it will make less and less sense to pursue a woman only to seduce her and then leave her, because you will want her to become part of your social circle. You will want to have the added enjoyment of her becoming friends with your friends.

You may be surprised to find that at times you are actually bored with your girlfriend, yet at the same time you do not want to leave her, because you have become accustomed to her company, your friends like her, and if you ditch her you will incur anger and recrimination not only from her but from your friends. Bit by bit, it just starts to seem like it isn’t worth it anymore, all the drama and pain, when you can’t go to any bar or club without running into some girl you’d rather not run into, all the dislocation, all the toothbrushes and underwear you can’t remember whose house you left them at, all the CDs and shoes and stuff.

So you’re going to probably end up with some girlfriend that you can tolerate long enough to end up really caring about, and then you don’t want to leave her and make her cry and have her throw things at you and have all her friends hate you and say bad things about you, so you’ll try to psych yourself for a long-term relationship. And that is when you will learn to modify your behavior a little, to appreciate things about her that take time to know. And then you’ll find that things get better if you stick around. And that is how society works to civilize young men and protect young women from their savage predations.

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Can a bigot be a good person?

Cary’s classic column from THURSDAY, JUN 24, 2004

He pursued me, but then rejected me because my religion was “wrong.”


Dear Cary,

Do you think someone who is narrow-minded and bigoted can truly lead a happy and fulfilling life? And can this person be considered a “good” person if they are good in other ways?

I went to an art exhibit/talk at a friend’s church. I was standing at the refreshment table and a man approached me and started talking to me. I thought he was just being friendly, but I realized he was quite interested in me and he asked me to sit next to him. He seemed incredibly excited about meeting me. Before he left, he wrote his cell number, home number and home e-mail on his business card and asked me to contact him. He said he hoped I would come back to the church again. I said I surely would, but made sure to let him know I was Jewish.

We went for a walk a week later. He seemed incredibly attracted to me, and I felt the same way about him. We were talking about where we went to college, etc., and I felt it was important to let him know my age, as I thought he might be a few years younger. I am 44, but look much younger. He said he assumed I was 35. He is 38. After a few more encounters, by phone, e-mail and in real life, he came clean and said he had been surprised to learn that I was Jewish and 44 and that those were complicating factors for him (he says he wants to have biological children).

Of course we all need to follow our preferences, desires and needs, particularly when it comes to children, but it is the way he rejected me — not based on my qualities and traits but on my bloodline — that floored me. He said in an e-mail that it was not possible to have a true and fulfilling intimate relationship (he’s never been married; I have been) when there was an underlying feeling that the other’s religion was “wrong.” I wrote back that I certainly didn’t see his religion as “wrong” (he’s Presbyterian, just for the record) but that he must think that of mine, and that, according to that line of thinking, Buddhism, Hinduism and Islam would be wrong, too.

I thought we shared the same values; he seemed so kind and thoughtful, and was very intelligent and funny.

I know there are Jews who will only date and marry other Jews, but I’m not one of those people. Most of my friends, of all religions and cultures, seem happy just to have found someone good, regardless of their background.

Who are these people who secretly feel that those of other religions (and one would assume other races) are inferior and wrong? Of course they are everywhere, but this guy seemed so good and kind. Do you think a guy like this will find happiness in a relationship, and in life overall? I am kind of hoping he doesn’t.

Surprised but Shouldn’t Be

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Dear Surprised,

You ask good questions. Before trying to answer them, though, let’s say what happened here: You were hurt by a man who was attractive but thoughtless. After being hurt, you moved from the event itself to a set of sweeping questions and indictments, as a way of trying to understand what happened. That’s OK. I understand what you are saying; I understand the impulse to do that, and I share your outrage and bafflement. I’m also interested in Christian religious doctrine and how individuals can use it, or distort it, in their interpersonal relations. I don’t know if he’s a bigot or just a little careless in how he expresses some struggle he’s undergoing.

But it’s a shame you couldn’t work together to build a relationship, since you had a lot in common. Perhaps the relationship could have gone further if he had been more diplomatic. Instead of being so doctrinaire, he could have asked you what you thought about interfaith marriage, and about adoption, and expressed his reservations about it. He could have told you what sort of struggle he’s undergoing, trying to reconcile his religion with his desire to marry and raise a family with a woman he loves.

It’s possible that he did not want things to go further, for personal reasons not having to do with your different faiths. If that’s true, it’s a shame he had to drag in all that other baggage. On the other hand, if he was truly interested and just did something boneheaded, it’s even more of a shame, and he may regret it. (I sense that you hope he does regret it, but if so, you might think about trying to let go of that anger, as it will not help you to carry it around.)

I know this from personal experience: If we’re nervous, conflicted, insecure or fearful about how someone is going to take something, sometimes we work on it so hard that we end up saying the worst thing possible. Instead of trusting my instincts to guide me in a conversation about it, I will mull it over and over, as if by this magical process of mental refining I will arrive at some essence that is the “truth,” that I can then deliver up in triumph and finality: Here it is. I’ve decided. This is the situation. It becomes like a presentation before the Supreme Court.

I forget that what I really need to do is have a conversation with somebody. It’s comical, because the harder you work on what you think is the problem the farther you get from the problem — because the problem is relationship, and relationship is not something you can do in your head. It takes both people being present.

It sounds like this guy didn’t really have a conversation with you about this, he just announced his decision. I take it that part of what wounded you was the arrogance, the presumption, the way he just announced as if from on high that he had reached a conclusion and you were out. I don’t think that’s the way relationships between equals are supposed to work.

You were perhaps also hurt in ways that you have not fully acknowledged. Being a Jew, how can you not feel the sting of even the slightest suggestion by a Christian that you’re not good enough, that you’re flawed, that you’re not allowed, you’re not the right kind, you’ve got the wrong beliefs, the wrong heritage, that, as you put it rather evocatively, you’ve got the wrong bloodline? How can you not be put in remembrance of atrocities committed against your people?

Was he a bigot? I don’t know. I do think he was thoughtless. His actions were far less than divine. I do not think Jesus would have broken up with you that way.

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I only have quick relationships

Cary’s classic column fromTUESDAY, APR 19, 2011

I get in and I get out. How can I slow down?


Dear Cary,

I have always been good at quick relationships. Any time I have wanted a boyfriend, I just started flirting and it wouldn’t take long before someone would invest in me. Relationships could start overnight if I just acted perfect enough. But they didn’t mean much when the truth came out. My happy demeanor would fade away pretty quickly once I realized I was in a relationship with a guy I either had nothing in common with or wanted nothing to do with. I would turn bitter and everything would go down in flames with the same intensity with which it started. Then I’m back at square one.

About a year ago I finally noticed the pattern, but I don’t know how to fix it. For example, I met a guy who really is nice and we talked through email for a few weeks before trading phone numbers. Two months of talking and I felt like I was losing my mind. I finally asked him if he was going to come visit me or not. It drove him away faster than I could realize what happened. I assume I was too pushy, but with my history of talking and having a committed relationship within a month, I am feeling more than lost.

I have thankfully gotten what I feel is another chance at having a very nice, funny and intelligent guy. He really is great and we’ve been talking since Feb. 28 of this year. It’s been mostly through email, but I already feel like it’s taking forever. Don’t get me wrong. I am not going to fall into that same trap of driving him away again. I just don’t know if I’m doing the right thing at all. Do I keep dating others and make myself busy? Do I take his silence as a sign? Is he just trying to think things through before getting ahead of himself? And if so, how do I calm myself down enough to not care in the meantime?

I feel like the girl who pulled the short stick in life and was never even taught how to fish with it. Please help me to learn so I can end this bad cycle. I want a relationship that isn’t built just on convenience.

Love-Stumped

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Dear Love-Stumped,

If you want a relationship that isn’t built just on convenience, then you have glimpsed a truth about real relationships: They are profoundly inconvenient. Being in a relationship means there’s another person there, different from you, likely to respond in unexpected ways to things you say and do. This brings excitement but can be frightening and difficult. If you want control and convenience, with it come shallowness and brevity; if you want depth and longevity, you’re going to have to give up some control and convenience.

One way to begin to deepen the relationship would be to ask the other person some questions. This can be fun. For instance, you could ask the other person if he wants to have a relationship. This may hit him by surprise. He may ask, Well, what do you mean? You may say, Well, I’m not sure, exactly. Just wing it. You could ask then if he wants to have a relationship with you, and what kind of pace feels right, and what he has been thinking about. The trick here is to just ask the question and hear the answer. You don’t have to do anything.

There’s no right answer. What you’re doing is participating in a new way that opens up possibilities instead of closing them down.
There is no way to know what his answers will be. But by asking these questions, you give up some control and invite his viewpoint. In the past, you have probably been basing most of your conversation on what you think his reaction will be. Now, you are not trying to have any particular effect. You are asking open-ended questions in order to try out a new way of being with others.

By asking this other person what he wants, you will find out in what ways the relationship may require you to inconvenience yourself. It may be that he wants to spend a day with you reading by a lake. You may not want to do that. So then you have a choice. You can continue to run your life without any interference from outside, or you can decide to allow your life to be altered a little by the desires and ideas of another person. You can spend the day with him reading by the lake.

He may decide he wants to kiss you by the lake. You may find this agreeable. Or it may alarm you. You may fear that you’re about to do the same thing you always do. To make it more interesting, you can ask him a question before you kiss him. Ask him, Oh, I don’t know, ask him what he thinks is going to happen next. Maybe he will say something witty, or maybe he will seem confused and dim. Hmmm. What would be a witty and engaging response? Well, maybe he would say that he expects when he kisses you that the earth will shake and the heavens open up. That would be an acceptable response. At least he’s trying. On the other hand, he might stare at you blankly, with paralyzing fear in his eyes, and this may take the bloom off your whole afternoon.

The only way to find out is to experiment. Be a scientist. Observe and formulate hypotheses.

Here is another thing you can do. Remember your carefree days as a child. When you were a child, you were not plotting so carefully. You were not thinking so much about what others might say or do in response to what you say or do. I suggest you return to that time in childhood and remember what it felt like.

Then try relating to others with some of that simplicity from childhood, some of that innocence. This is just my idea. I’m no psychologist. But sometimes when I am too confounded and my thoughts are racing, this is what I do. I approach people simply again, as a child.

Remembering childhood relieves us of the burden of knowing what will happen next. We have no idea what will happen next. We’re just kids!

Think of childhood. Forget the rules. See what happens.

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Attracting the wrong women

Cary’s classic column from WEDNESDAY, APR 23, 2003

There’s a kind of girl I like, but I don’t seem to get anywhere with her because I don’t speak the “cool people” language.


Dear Cary,

It’s been about three years since I started messing around with the online personals, after a tough breakup. During that time there was a nine-month relationship with a girl I met through friends who was “nice” but not exactly passionate, and we’ve deescalated into friends. Besides that, my dating life, though busy, has consisted of short episodes of e-mail/phone/dinner, rarely more than two dates, and that’s it. It’s almost always my choice not to continue, because it seems like I meet the same type of woman over and over again — in real life or online. I’m a pretty steady healer-type and people who respond to me in a romantic way tend to be high-strung, fairly insecure and fearful to an extent greater than I want to have a future with.

There’s another type of girl out there whom I see, make contact with and occasionally get responses from. This is the cute-as-hell, supercool, awesome, funny, smart sort of woman who really does it for me (and everyone else). We might go out on a date or two, but they don’t seem very interested. I think there’s some sort of language I don’t speak — the “cool people” language — and I know that to relate to the kind of women I want in my life I must speak it, but I don’t understand a word. This is getting to be a real bummer on me, and it’s hard on women who think we’re starting something and then get (gently) dropped.

I don’t start much of anything anymore anyway — seems sort of pointless with this broken record cycle. My amorous feelings are generally either dormant or anguished at having been woken up by someone who’s not interested. Can you offer some perspective, perhaps some changes to make or other ideas? My occupation and hobbies don’t put me near women on an activity-oriented basis, so the personals seemed like a good idea but it’s just not working out, at least not the way I’m approaching it. I know these things take time, but it’s been so long since I’ve been able to say the L-word and mean it in every sense.

Water, Water Everywhere

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Dear Water,

I know what you’re talking about. There’s a kind of person who shines, who is quick and bright and hard to catch, around whom it seems that life is sweeter, lighter, faster. And you want to ride in their cars and go to the parties they go to. But when you get in the car suddenly you’re like a bag of concrete in the leather seat, dusty and inert, and they look at you and you know they’re thinking how heavy you are and how unpleasant it’s going to be to have to carry you on their backs all the way up the steps of the glamorous house up in the Hollywood Hills where Ice-T lives.

All I can say is, you have some choices. You can be the slightly uncool guy who’s always in the background, as if silence and shadow followed you around; there’s a penumbra of uncoolness about your head so that it’s almost hard to see you even in the bright sunlight. You can be that guy if you want, if you feed on this action and you can stand not to be in the spotlight, can stand being the driver, the fetcher of cocktails, the one who always goes for beer.

I have been cool and I have been uncool, and cool is pretty good, but uncool is better. Cool is too much work; you have to be an athlete of ennui, a virtuoso actor of sweet nonchalance, you have to look as though where you just came from was the most fabulous place in the world except for the place where you’re headed to. You can do it if you study the movies. But you will always be pretending that you don’t wake up lonely and afraid in the middle of the night.

For all I know, maybe you don’t wake up lonely and afraid in the middle of the night. What do I know? My guess is that you’re an introverted sensing type who’s attracted to flashy extroverted intuitives. (As who wouldn’t be?) So by the time you’ve formulated a sentence about the weather they’ve already summed up the history of condoms and what’s wrong with Madonna. It’s dizzying and fun to be around them, but you always feel a step behind. Well, you probably are a step behind, but your steps are bigger and more solid.

Here’s a thought: If they have something you want, why not try to find out where they get it, and then see if you can get some yourself. Go to the places where they go. Listen to what they listen to. Take some of their drugs. See their movies. Because you have to start to feel the way they feel, and the cultural productions they consume contain the shape of their feelings and attitudes. You might be able to enhance your intuitive sense of where they’re coming from if you immerse yourself in their cultural milieu.

And, if my wild guess is correct, and you’re more oriented toward sensing, you can do stuff they can’t do. What can you do? You can take all that money you’re making doing some boring, solitary, analytical job and get a big house and have big parties where everything is just right. You might always be the Gatsby in the background, making sure the caterer gets tipped. But at least you’ll be in that bright, dizzying world.

I know this may be a little more elliptical and all-encompassing than you were hoping for, but I think your small problem represents a lifelong orientation, so you might as well think big.

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I’m 32 already. Time to get married!

Cary’s classic column from FRIDAY, SEP 25, 2009

I’m tired of fooling around with guys who just want one thing


Dear Cary,

I’m still single at 32 and hate it. I absolutely want to find and fall in love with a man I can spend the rest of my life with. The problem is, I keep ruining things by sleeping with men too soon, often right away. And each time I make this mistake, I am left even more hopeless, feeling worthless, terrified and convinced that I’ll never find a man who wants more from me than sex.

Here’s the latest: I met a great, handsome, friendly, smart, nice guy at a friend’s barbecue. We clearly hit it off, had immediate chemistry, and proceeded to flirt all day. After the barbecue, we all went out to some bars, and we all got pretty drunk. I and my new man-friend continued to flirt, which eventually turned into making out on the dance floor. Fast forward an hour or so, and I’m happily going home with him, and we spend the night together. The next morning is nice, we exchange information and make plans to see each other again. But after our first real date, I never hear from him again. Because this is not my first rodeo, I slowly come to realize, AGAIN, that I’ve completely ruined any chance he and I ever had by sleeping with him right away. And it’s my fault; I ruined it and now I feel absolutely worthless. The whole thing crashes down and it’s MY FAULT. My fault for being spontaneous, for wanting to have fun, for being a fun girl. It’s MY FAULT because it’s my responsibility to say no, to know that a guy couldn’t possibly stop it and beyond that, has no reason to do so.

I keep following this pattern even when I know it won’t bring the outcome I want. But in the glow of the evening, all flushed with flirtation and fun and devil-may-care attitude, I just want to go with the flow, enjoy myself and have some fun. It seems like I have only two options — be myself, have fun, and then get rejected; or be constantly on guard, suspicious of all men, keep them at arm’s length, and maybe get a second date. Neither option seems ideal, but obviously the one I keep choosing is ultimately not going to get me what I want. I try to convince myself that I’m this sexually confident woman who doesn’t follow traditional gender roles, but really I can’t help believing that deep down, I’m just an insecure slut. I get opposing messages from all kinds of media — books, movies, magazines, etc. — some telling me that I should wield my sexual power how I see fit, others saying I should hold back “the goodies” for three dates, or one month, or 90 days, etc. So now I’m asking you. Am I sexually liberated, or just a slut?

Eternal Bachelorette

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Dear Eternal Bachelorette,

I don’t think this is about being either sexually liberated or just a slut. I think it’s about your desire to move from one stage of life to another. It is sad to give up the fun and carefree ways of your current life. This behavior has given you much joy in the past. Yet it is not serving you now. It’s making you unhappy. So you know you must give it up. But you keep doing it.

You don’t think there’s anything wrong, or bad, with what you are doing, but you don’t like the results.

There was a time not long ago when you were fine with what you’re doing. So what changed? You changed. You want something different now.

There’s nothing wrong with that. It’s a good thing.

But how do you become ready to move from one stage of life to the next? It helps to openly admit that it’s going to be sad to leave this stage of life you’ve enjoyed so much. If there were a ceremony to signal your readiness for this change, that would be nice. Perhaps there are, or were, at certain points in your life, but their efficacy was lost, or they were not held at the correct time. But this is no joke.

If you meet a man you like and you are afraid you are going to do the same old thing you always do but want to do something different, before you do anything, call yourself a cab.  Assume that you have nothing to lose by being frank and strong with this man. While the cab is on its way, take this man’s hand and lead him away from the crowd and lean him up against the wall behind the dance hall and tell him that you are so attracted to him in such a special way you’re likely to fuck him right then and there if he doesn’t call you a cab.

If he says, “OK, you’re a cab,” maybe there is a possibility. Put a GPS device on him. Tell him the cab is already coming, you know how to call cabs yourself. Get out of there. Pray that the cab comes fast.

Leave. Go home. Take a shower. Drink some tea. Get some sleep.

Give away what you have been withholding and withhold what you’ve been giving away. That doesn’t mean follow “The Rules.” It means get real. Tell him you want a man to fall in love with and stay with, and if that’s a problem for him then OK there are plenty of chicks. Plenty. Next. Not to be crass. But you have to come from a place of complete honesty and vulnerability and pain. Because if you want a lifetime relationship that is what it will be full of: honesty and vulnerability and pain.

It’s complicated, OK? Every pattern of pain is different. It’s your fingerprint of pain. It’s your snowflake of pain. Everyone is a little bit funny. So study yourself. Begin a course of spiritual growth. Begin meditating daily. Begin asking yourself big, open questions and being ready to receive the answers.

If you seem to be “difficult” or “can’t make up your mind” or are “wasting this dude’s time,” fine. Waste this dude’s time. You are not looking for a dude who is checking his watch to see if you’ve taken your clothes off yet. Not because you’re playing him but because you’re doing just the opposite: You’re being your true, cautious, wounded, loving self. Because for once you’re going to take care of yourself and value your own timing. You do not want a man who is in a hurry. You do not want a man who is looking for convenience. 7-Elevens are convenient. People don’t get married there.

You’re ready for a new kind of life. Open the door to it thoroughly, passionately, completely, and I have a feeling it will come.

Act now for best results.

Boys leave

Cary’s classic column from Wednesday, Jan 28, 2004

Why was I the cat’s meow on the fifth date and a sex buddy by the sixth?


Dear Cary,

So it’s happening again: Girl meets boy. Girl likes boy. Gets boy’s number. Girl and boy begin dating. Boy sends all of the “very interested” signals. Girl responds in kind. Incredible sex. Eye-gazing. Natural feeling, intelligent conversation. Then the sixth date: No eye contact, little attempt at conversation, unimpassioned sex. Boy abruptly, awkwardly leaves that morning, making no mention of weekend plans. Boy insults girl with small talk. Girl feels used and disappointed. Girl writes Cary.

What’s going on here? Seriously. This has happened to me before. But I didn’t expect it from this guy. He’s 33. He’s in med school. He’s traveled extensively with the military. He’s bright and clever. He lights up a room. He has a zest for life that’s devastatingly attractive to me. He’s confident.

My male friends tell me that I intimidate guys. I’ve tried to tone it down. With this guy I really took it easy. Followed his lead. Was always very much myself but let a little more of the softness through. I avoided all the old traps. It seemed to work. I was pleased with myself for breaking old patterns. Then, sure enough, with no warning he’s gone. Vacant.

Typically this is when I begin to act like a circus clown, jumping all around trying to pinpoint whatever it is that will take him back to where he was before, and this is when it gets ugly and I get pathetic, and the whole thing is scrapped (usually with good reason by then). But I really don’t want that to happen this time. I want to change this pattern. I want to understand what’s going on here.

I really like this one. I do. I rarely meet people that are as passionate about living as I am, and it felt so nice to not feel like someone’s specimen. He doesn’t need my energy to feed off of — he has his own. I trusted that he wouldn’t be another man who would profess how incredible I am and then in the next breath tell me that I’m “too much.”

I feel hurt and disappointed. How was I the cat’s meow on the fifth date and a sex buddy by the sixth? Cary, can you tell me what happened at five and a half? I can’t think of anything that I did. I really can’t. I’d tell you if I could. Why did he turn off, and more importantly how should I respond? Typically I would call and confront him (weirdness ensues), but this time I want to see what he does, and what you say, before I make a move to unearth whatever’s going on.

How should I proceed? And is there some way I can avoid this in the future?

A Little Broken Hearted … Again

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Dear A Little Broken Hearted,

As I go over your letter, trying to locate you, the image I get is of a woman spinning wildly like a child on a gleaming ballroom floor, throwing sparks into the night, arranging the very universe by her dancing, drunk with attractive power. I see a woman who looks only outward at the shiny, spinning world full of lights but never inward lest she fall, a woman who sees around her other shiny, spinning, fabulous dancers and is briefly drawn into their orbits as they are drawn into hers, forming figure eights as they orbit each other on a great dance floor in some marble ballroom. It is a fabulous, glittering ball, half-mystical, and in this ballroom there is no conversation, only dancing and gesture; nor is there any progression, or any time; there is only whirling and more whirling and when the whirling stops there is only a dreamless sleep of exhaustion in plush red banquet chairs, and then more dancing. There is no remembering of hard times here in this ballroom, nor is there any self-doubt, nor are any names exchanged. No one can remember the last time the music stopped, and no one can remember the last time a contemplative word was uttered. This is not a place where contemplative people come; it is just a whirling ball, glittering and festive and timeless.

That is how I picture you, as a glittering dancer at a ball, who met another glittering dancer and danced wordlessly until you exhausted him and then he whirled away. But when he whirled away you were sad. You expected something else. But what was it you expected? No one in this ballroom knew that you expected anything else. All anyone does here is dance.

This man who turned away from you and hurt you: What was the substance of your understanding of him? What did you learn about his wishes and desires? Was he looking for a wife, or just a playmate? Was he completely single, or partially attached? Was he what they call “emotionally available”? Do you know how one would go about ascertaining if someone is “emotionally available”? Did you consider that a handsome, worldly, charismatic former military man who is now in medical school might be in some ways not emotionally available? Did it occur to you that in your busy, whirling extravagance of spirit you might have neglected to closely study his eyes, how he reacts to you, whether he’s shrinking from you as you expand to fill the room with your fabulousness, whether he might have appeared short of breath as you sucked the oxygen out of the air around him, whether you might have missed any attempt on his part, however subtle and coded, to warn you that he was not the man for you?

It may be that you have great attractive power but only have transactions, not relationships, with men; that would explain why men come and go from your boudoir at will — because although you may dance with them and sleep with them, you have neglected the careful disclosure and attentive listening through which two people establish an emotional narrative. You almost sound like a woman in the last stages of a magical girl phase, when you still have the power, intelligence, vivacity and attractiveness of youth to draw men to you, but find that drawing them to you is no longer enough, that you are groping your way into the world of difficult compromise and self-disclosure that adult relationships require.

If you are ready for that, you will find your way. Here is a tip: The next time you are attracted to a man, try to see him not with your eyes but with your heart. Ask your heart what it sees. It may not see the glittering prince that you see with your eyes. By your heart I mean your intuition, your spider sense, the instant feelings of fear or attraction that you used to rely on as a child.

You’re going to have to stop dancing and making love long enough to hear what the next man has to say. What he says may surprise you. It may also bore you. Such is life outside the ballroom and the boudoir.

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Why can’t I find a relationship that will last?

Write for Advice
Cary’s classic column from FRIDAY, JUN 6, 2008

Am I destined to be lonely? Do I pick the wrong men? Why am I still single?


Dear Cary,

I believe that I have lost my ability to trust my judgments on relationships. However, I still believe in love, and I have not given up all hope.

Here is the situation.

I am 33 and single yet again after another failed relationship. I am college educated, I work a high-pressure job, have quite a large group of close friends, and have some hobbies that I am pretty devoted to. So I guess you can say that I am not one of those people who is desperate for a romantic relationship out of fear of nothing else going on in my life.

I have always found the dating world difficult, but this is mostly due to some lingering self-doubts that have been around since high school. My dating life so far has been approximately five serious relationships. The longest (which was my college boyfriend) lasted about five years. It was a very ugly breakup, and I didn’t really get over it for close to two years. I could casually date, but would normally pick up guys with various issues (drug, alcohol, honesty problems, etc.).

I met a seemingly good guy who didn’t seem to come with excess baggage when I was 27, and had even made plans to marry. It seemed like a pretty normal relationship, and by far the most stable of my life. He broke up with me at the three-year mark, and immediately moved in with a girl from his grad-school class. (They married months later.) This situation pretty much floored me, as at the time it pretty much came out of nowhere. I went into therapy, and realized that there were lots of red flags in that relationship that I just didn’t see at the time. However, I was eventually able to move on, and not let the sadness completely ovewhem me. It was extremely difficult. I do sometimes believe that I carry some major scars from that relationship, but none so bad as to make me “give up.”

I then found myself falling in love with a friend of mine whom I have known since college. Hanging out with him was always a riot, because he is somewhat of a smartass, and is someone I can converse with on just about anything. However, he also has a rather serious binge-drinking problem, and could sometimes be difficult to deal with during one of his famously ugly hangovers. I realized that my constant interaction with him was very unhealthy for me. So I went back into therapy, and got some clarification on why I felt this way, even though I knew it was a hopeless situation.

My friends, who are good-natured, could never understand why I was constantly having these issues. I would get “You are really smart, really pretty, really interesting, etc., etc.” (I am also the only one who is not currently in a long-term relationship or married.) Some of my friends even went so far as to try to set me up on blind dates, but there was no real spark. I even jokingly said that I had developed an allergy to dating. But the reality is, I would love nothing more than to be in a satisfying relationship with a nice man who has charisma and can make me laugh.

My therapist mentioned quite a few times that I was doing the right things by keeping myself active, not trying to over-focus on finding a nice guy, and staying motivated with my hobbies. I work out quite a bit, and play several sports recreationally.

So now to my latest situation. I wasn’t looking for a serious relationship immediately, but was looking at trying to see where things were progressing. He showered me with attention, and while it was a little overwhelming at first, it was nice. He seemed pretty levelheaded, and we seemed to share quite a bit of interests, and had like backgrounds. While I was still trying to completely let go of all the feelings for the friend with the drinking problem, actually dipping my toe into the dating pool really seemed to help that situation.

However, out of nowhere, I was broken up with. When I asked for the reason, I was given “stressed out because of work” as the reason. I sympathized, and was told that, however, he still wanted to be friends. I have now found out that the real reason was that he was getting back together with his ex-girlfriend — the same ex-girlfriend who had screwed with his emotions last year. I was upset, but not so much for him going back to the ex-girlfriend, but by his lack of candor. I have once again lost my ability to trust. Even by keeping casual, and not being clingy, needy, etc., I still feel as though I have failed once again, and picked a guy who obviously has some major issues.

So how can I learn to trust my own instincts again? I feel like my guard — which I find naturally difficult to let down but which was once again finally coming down — has gone back up. I feel extremely jaded as maybe I am destined to be alone, yet somehow I still hope that maybe I will find a nice man who will not be a complete jerk. If I am “doing the right things in life” according to my therapist — to place the focus on other parts of my life — why do I still feel that empty feeling that borders on jealousy when I see my friends who are happy? I also question how I can ever really relax enough to take another chance if I seemingly have really questionable attractions in men.

Yet Another Brick in the Wall

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Dear Brick,

What is your reason for seeking a man? It may sound like a dumb question but … Is it to have children and raise a family? To avoid loneliness? To feel relaxed and confident in your world? To enjoy sex? To demonstrate your value and attractiveness to others? To keep pace with your friends? Perhaps with your therapist you can dwell on these questions long enough to see some specific and detailed answers emerge. This might help you in several ways. For one thing, it can help you see exactly what you are losing when a man goes away. And so it can help you think how to replace those specific things that he was providing. If he was providing sex, for instance, and you miss the sex, then you can set about trying to find more sex. If the ache you feel is loneliness, then perhaps you need the company of others. If you feel wounded or betrayed, then perhaps you can work on that woundedness, exploring it, asking, Is it anger toward him, is it shock at how I have been treated?

So rather than suggest how you might better find and maintain another relationship — for which many guides exist — my approach is more to explore the various aspects of having a man and see how having a man is connected to your larger life aspirations.

If you can define how finding a man relates to some larger aspiration you have — to have family, to be connected closely, to have security or to avoid being alone — then perhaps your true desires will become more specific and vivid, and you will come to see how your past relationships fit into a larger pattern, and you will not feel that everything is so hopeless. Patterns will start to emerge. You will start to see what your big struggle actually is. You will start to see a direction. The direction may involve a relationship with a man or it may involve something entirely different. You may find, for instance, if you sit with this, that some vocation is pulling you in a certain direction. The direction may not be clear to you but it will become clear, if you can settle down and try to see what is in the distance.

This pattern that causes you so much pain may be a very natural thing and not a problem at all. It may be a sign of a certain direction that you are being called to go. If you quiet your mind and let various images come to you, you will see this. I wonder what those images would be.

You have a rich life filled with friends, work and activities.

Right now, I sense that you are keeping busy partly to distract yourself — from what? From these “lingering self-doubts,” I guess. And what those lingering self-doubts are, in truth, I imagine is the truth of your being.

Men come into your life and go out of your life. Men do not act the way you want them to. Their feelings change, or diminish. They drink too much or take drugs. They lie. They have something that you want but then the relationship turns painful. What is the pain about? Is it feeling that you will always be lonely? Is it feeling that others cannot be relied on, that they let you down, that they take advantage of you, wanting only sex and entertainment and then moving on? Is it a feeling of futility about the future, that you will never have the life you dream of having?

After looking at this for a while, ask yourself, Is this the big thing? Are these relationships with men my purpose in life? No? What is my purpose in life? Do I really want to get married? Is that the big thing? Or is it something else? Do I really want to be a singer, or a gardener, or start a business?

So how about this: Make this year your year of digging deeply. Make this year your year of facing the shit. If you can do that, you can find out who you are and where you are going. Then these other things will seem minor. You will reach a point where you look around and see that having a boyfriend or not having a boyfriend is not the issue. You are 33 now and no longer just out of college, no longer frolicking about. Your life is right here before you. The issue is how you get up in the morning and face your life. People will come and go. Your friends will come and go, too. Your family members will age and their status in life will change, as yours will. Try to see the big picture.

Underneath all this worry, there is a distinct, unique, thriving person with a powerful voice and a distinct view of the world, and capabilities no other person has. Maybe that person does not want to fit in and get married. Maybe that person wants to run away and be a crazy woman, live in a shack on the highway, or be an inventor, or an architect, or a criminal, an actress, a helper of children, a writer, a telephone operator …

So there I go again, ranting. But I want to clear away the generalities. I want to ask you to spend this year understanding your life in a new way with the help of your therapist. I want to ask you to identify your deepest beliefs and desires and work with her to understand how they have created these patterns that cause you so much pain, and figure out ways to get where you need to go. I think you can do that.

Cary Tennis Newsletter Sign Up

Warning signs

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Cary’s classic column from WEDNESDAY, NOV 12, 2003

I’m in love with her, she’s in love with him, and I feel like a confused, heartbroken sucker.


Dear Cary,

A few months ago, I had a one-night stand with a co-worker. She had recently been seeing another co-worker who broke her heart because he used her as a sport fuck. But she was in love with him.

After our first encounter, we agreed that our thing was a mistake and we decided to not let it happen again. But it happened again, and again. We saw each other for a couple of months. Then one night, after I had grown tired of keeping our relationship a secret, she tells me that she slept with her ex (our co-worker) while she was seeing me. I confronted him about using her again and I freaked out on her for letting herself get used. Our relationship ended, but we remained civil since we all worked together. That lasted all of about three weeks. On my birthday I got a call from her and she invited me over to her place.

We started seeing each other again for a few months. She told me when we started up again that she was not ready for a relationship and that she couldn’t promise me anything. I was fine with that. I really liked her and wanted to give her space. But she’d call me every day. After a few weeks of this, she told me one day that she was finally feeling comfortable with the whole thing. Things were going well. And I was falling in love with her. I even left my job (for a better one), partly so that we wouldn’t have to worry about working together anymore.

About a month ago, I called her before I left to visit relatives out of state. She was totally shut down and refused to talk to me about anything. She told me that she needed alone time. I lost it. I demanded to know why this came up out of the blue. I told her it was over between us. I was done with her wishy-washy behavior. Right before I hung up on her, she told me that things could still be good between us. Two days after the “alone time” speech, I called her and she told me that she changed her mind. She told me she wasn’t ready for a relationship — not with me — not with anyone. I said some nasty things and told her that she would probably wind up having a “relapse” with this snark co-worker who broke her heart.

I’ve called her and e-mailed her several times demanding an explanation. Finally she told me that she was still in love with our co-worker. And while she knows it’s not reciprocal, she can’t help it. I also learned that he used her for sex yet again. This infuriated me because it meant that I had been heartbroken over a lie. She was perfectly willing and able to have a relationship, just not with me. I still care for her and love her. She’s hurting herself by chasing this windmill. Now she refuses to talk to me. Meanwhile, she told him just about every little detail of the relationship that she and I had. I feel like I’ve been sold out.

I should have seen the signs. But she sent me mixed signals. I suppose I believed the good ones and ignored the bad ones. Why am I the one being punished? Why is she confiding in this asshole who uses her and refusing to talk to me? I’m over the fact that she doesn’t want to be with me, but I want to be her friend and she won’t even let me do that.

Totally Confused Heartbroken Sucker

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Dear Totally Confused,

Your house has been burning for months now, but you keep running up to the flames and getting burned. You can’t seem to take your eyes off the spectacle of destruction. You’re drawn to it. You’ve got to turn around. Look away from the fire. Let your eyes adjust to the darkness. Go carefully in the other direction. Keep walking until there’s no more heat on your back and you can’t hear the roar. Find someplace cool and safe where there’s first aid. And don’t look back.

It wasn’t your house anyway, it was just a place you were staying because you hadn’t thought of anything better to do. So once you’re safe and your burns have healed, look for something better to do. That’s your job now. Casual hookups and one-night stands are fine if that’s what they are. But if you’re really looking for a more stable, committed relationship, then don’t expect casual things to turn into something else. You need to get clear about your intentions with women. If you’re the type of guy who’s likely to fall hard for a woman, then make sure the woman you fall hard for isn’t going to burn you.

In the meantime, to help you more fully understand your situation, maybe it would be helpful to make the distinction between a wound and a problem. The difference between a wound and a problem is that the problem can keep wounding you. A wound just heals. As long as you stay away from her, you don’t have a problem. You just have a wound that needs healing. Now if you go out and take one more look at that fire, and get burned again, then you have to start all over with the healing process. So stay away from the fire until you’re healed.

What would it mean to be healing? It would mean that even if you do on occasion think about her, even if you feel occasional pangs of regret and longing, you can honestly say to yourself and to anybody else that you’ve made a decision to let that episode go, that you fully understand you have no role in it anymore, that it’s none of your business — none.

Here’s a suggestion for the future. Next time, take it slow. Do not go to bed with a woman right away. Give it some time. Get to know her really well. Find out where she’s at emotionally. If she’s getting over a boyfriend, back off. What you need to look for is the ultimate clean, unencumbered, uncomplicated kind of romance, full of slow trust and careful commitment. It might not sound like so much fun, but, frankly, you’ve been a little reckless with your heart. So guard it more closely. It’s your heart. Be careful with it.

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I’m 38 and want kids, but the men I’m dating don’t

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Cary’s classic column from TUESDAY, OCT 11, 2005

Since divorce, life has been pretty swell, but now I want to settle down and be a mom.


Dear Cary,

I was violently thrust into the dating inferno after my divorce nearly six years ago. During that time I’ve run the gamut of interactions: everything from being played like a plastic Flutophone to having a couple of semi-rewarding, longish-term relationships to enjoying a few purely physical hookups.

During my period of self-actualization I’ve done the following:

Gotten a shitload of therapy

Realized creative dreams of writing and getting published

Learned how to parallel park on steep hills (on the left side)

Amassed a huge network of fabulous friends

Made peace with my ex-husband

Learned French

Got promoted and learned to accept, if not fully embrace, working for the Man

Traveled

Turned my ex-boyfriends into great friends

Learned to love yoga in 120 degree temperatures

According to the post-divorce survival guide, I’ve done everything correctly, yet I still can’t figure out why I’m approaching 38 and single. I have no problem getting dates, but finding someone who will, well, stick in this city has been problematic.

So, here’s my question. Lately I’ve found that the wonderful men who have been wanting to date me don’t want children. Either they’ve had their chickens or their need to create is sublimated by their artistic passions. I am still passionate about having kids. So, Cary, do I need to grow up and accept the fact that having kids may not be in the cards for me and allow myself to yield to these men who woo? Does it make sense to get attached to someone who isn’t on the same page? At what age does a woman throw in the towel? I’ve entertained having my own child, but lack of money and familial support make this a nearly impossible option.

Still Holding the Towel

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Dear Still Holding the Towel,

If having children is truly, absolutely, positively, without a doubt the one thing you most want to do above all other things, then you will have to make some major life choices, and quickly.

So please ask yourself how badly you want to have children. It isn’t enough to say you want it really, really badly. The question is, what are you willing to give up? Do you want it badly enough to give up living where you live and working where you work? Do you want it badly enough to compromise on the kind of man you raise those children with?

Or do you want to continue living in the city you love, working the job you have learned to appreciate, but just add a fabulous husband and a child or two — and perhaps a larger residence to accommodate the extra people?

If you’re willing to make significant sacrifices, and you start immediately, perhaps you can find a man, and a new home, and a new job, and get pregnant and raise some children.

But if you want to keep what you have and simply add some beautiful kids and a great husband, I would say the chances of getting all that are considerably slimmer.

So which is better? The fabulous life you have now, or the life you might have if you sacrificed what you have for what you want? It’s a matter of great unknowns and probabilities.

The situation is made more acute, of course, by your age. You are already well past prime childbearing age. You’re 38.

It’s not as though you’ve wasted these years. You’ve had a fabulous time. You could not have had this fabulous time if you’d been raising kids. Nevertheless, inexorable time has crept up, lessening your chances of conceiving.

We make choices.

So these are the two choices as I see them: 1) Devote everything you have to your one goal of getting married and having kids, which means being willing to compromise on everything else — job, city, man. Or 2) Devote substantially more energy than you already are devoting to the problem, but retain those elements of your life that you already know make you happy. That way, you may win the lottery and get everything you want, but if not, you have not given up so much.

My conservative bet would be on No. 2. Because even if you gave up everything you love to pursue the goal of getting married and having kids, there’s a reasonable chance that you would rush into something with the wrong man in the wrong town and the wrong job, and you’d be miserable, and you would have given up what you had. So the potential downside is considerably steeper; also, you might find that having children does not make you as happy as you thought it would.

So I suggest you stay in the city but narrow your dating, focus it only on men who want to get married and have kids. Put 100 percent of your effort behind that. Weed out the rest.

You may very well find a great man and get married and get pregnant and have some wonderful healthy kids and live happily ever after. Or you might adopt some kids. Or you might fall in love with a man who already has some kids. Or you might just enjoy your life as it is.

Believe me, not having kids is not the end of the world. For some people, in fact, it’s more like the beginning.

Cary Tennis Newsletter Sign Up

Dragged into the ring

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Cary’s classic column from Thursday, THURSDAY, JAN 30, 2003

My boyfriend promised we’d be engaged by Christmas but we weren’t. Should I let it go or move out?

Dear Cary,

I have been dating my boyfriend for four years, and living with him for most of that time. We started (I think mutually) to discuss marriage about two years ago. I took a positive but relaxed attitude about it at the time, because I figured that it would come when it came. But it didn’t. I said about nine months ago, “Are we getting engaged?” and “When?” and was told not to bring it up again because it would ruin the surprise. This led me to believe that something was coming soon. Nothing happened. About a month before Christmas I brought it up again and my boyfriend told me that we would “definitely be engaged before Christmas.” I thought that this seemed rather noncontroversial, so I was pretty happy and relaxed.

Christmas, as you might guess, came and went. I got some nice stuff but no ring. (I am not ring-obsessed … I don’t want a big ring or even particularly a ring at all, but it seems to be the only way that I can talk about getting married with my boyfriend.) I brought it up about five days later, and got the “I was very busy before the holidays, etc.” runaround. My boyfriend has a fairly demanding job, but he works about two blocks from the diamond district. I would think that if he took one or two hours during the day to go pick out a ring, he could stay later at night. It is also not a money issue.

I didn’t spend a lot of time recriminating him. I have decided to work something out myself rather than bring it up again to him. My attitude is that he knows how I feel. We have been together a long time, and there is a point at which it is either gonna happen, or it ain’t. I am not looking for a husband, but I am looking for my boyfriend to be my husband, and, if he doesn’t want to, it is time to do what is painful and break up with him if that’s not what he wants to be. He does not seem to be brave enough to tell me himself, but if he wanted to get married, well … you know.

Our lease is up in the summer. I am thinking of saying then that I am getting my own apartment. Should I say something about that now, to tell him where I am on this, or should I just wait and continue to hope that we’ll get engaged before then and that nobody will be the wiser? I don’t want to pull some ultimatum shit two weeks before our lease is up, and I also would feel sort of sneaky looking for an apartment on my own while he thinks everything is fine. But I also don’t want to end up getting engaged in a hurry only because he doesn’t want to suffer the trauma of my getting my own apartment (I think he feels a bit too comfortable with our relationship as it is). I think that he would interpret “I’m getting my own apartment unless you get me a ring” as a threat meant to hurt him, but it really is only a fact, and something that will hurt me, too.

My boyfriend and I get along very well. We had problems during the first year or so of our relationship, but I think we’ve worked them out. There doesn’t seem to be a third party in the picture. My boyfriend seems happy to see me at night and he doesn’t disappear mysteriously or anything. There are no previous marriages or children on either side. We like our apartment and our life together. I can’t see that I would be happier alone, or happier with anyone else, but, honestly, I am not happy living together indefinitely like this. It’s fine for some people, but it’s not what I want out of life.

Sad

Dear Sad,

This reminds me of something that happened over 30 years ago, when I was wrestling. I was in junior high school and going out for the team. If you wanted to go out for the wrestling team, you got up early in the morning two or three times a week and dressed out and went into a little concrete block room, the wrestling room, and stood around a mat. The coach stood in the middle and demonstrated holds and asked for volunteers for various holds. Then there was a kind of round robin where volunteers stepped forward one by one into the ring. You didn’t hold your hand up or ask permission, you just stepped in and wrestled. We had been doing that for about 15 minutes, and most of us had stepped in and tried our hand at wrestling. And then the coach said, OK, those of you who have stepped in, I think you want to be wrestlers. And those of you who didn’t step in, I think you need to ask yourselves if you really want to be wrestlers. Because if you want to wrestle, you step in the ring.
I was startled but relieved, because I didn’t know it had been a test. And it wasn’t a test, really. It was just reality. If you want to wrestle, you step in the ring.

I think you need to tell your boyfriend that, based on his failure to buy the ring, you have reached a painful but inescapable conclusion that he does not really want to marry you. You can’t hang around and let him play you for a sap.

After you tell him that, and start making plans to move out, the ball is in his court. If he wants to woo you back, if he wants to convince you that you’re the most important person to him in the whole world and he wants to spend his life with you, he’s free to do his best. Because I remember what else the wrestling coach said. He said this doesn’t mean that the rest of you are off the team. If you want to prove that you’re wrestlers, he said, you can prove it. But I’m not going to drag you into the ring.