Category Archives: Dating


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

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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


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


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


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


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.


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.


Help! I’m getting older!

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I’m not ready for cats and pottery class, but I don’t know how to deal with the fear.

Cary’s classic column from TUESDAY, FEB 7, 2006

Dear Cary,

I find myself pondering the notion of dating again after the demise of a long-term relationship. I’m female and in my late 30s, and I find myself increasingly self-conscious about being “an older woman” on the dating scene. While I’ve always been aware of the power of female youthfulness, the volume of that cry for the young ones seems ever-increasing, and sometimes it gets downright mean, as if women who age do so out of spite. In this big bad Northwest city, it seems cruelly competitive, and even scrolling through the letters section of Salon, I come across nasty references to women’s “expiration dates.” I can’t say I blame men for wanting to date younger women, and I’m not looking for an explanation or justification for this state of affairs. I know men face ageism in dating, too, but it’s far less common on the other side of the gender fence. The whole thing scares me and I don’t know how to deal with that fear.

I do have a few things going for me in the midst of this onslaught of matron-itis: I keep myself in great shape, I delight in all the feminine trappings — from fishnets to backrubs after a guy’s had a hard day to debating politics because it’s sexy, plus I’m blessed with excellent health. While I don’t lie about my age, I could shave off some years and successfully pass (but it’s not about that for me). While I’d like to have a serious relationship (marriage, most likely) with kids in our shared life someplace, I’m not at the mercy of my biological clock. I wouldn’t mind adoption, stepkids, foster kids, or even just being the crazy aunt ‘n’ uncle to the kids down the street. So I’m not racing against time in that regard, which relieves some pressure. Plus, I am pretty flexible about age myself. If some beguiling 58-year-old presented himself as a potential suitor and we were compatible, I wouldn’t think twice about hopping into his sidecar and blasting down the road with him.

I’m not the type to adopt a fire-sale mentality when it comes to dating — hardly desperate, hardly dependent upon a man to define my value. But I still find myself psyched out by the fact that I’m not as young as I used to be, and that that may count against me in more cases than not. I don’t need to hear that I should date in massive volume to better my odds or that my own self-worth is more important than the worth anyone else might ascribe to me. I simply would like you to tell me, friend, how exactly to run between the raindrops of this age thing? I’m not quite ready for cats and pottery class.

Scared of Math in Seattle

Dear Scared of Math,

There are people who can give you advice on dating and so forth, but I don’t think I’m that person and I don’t think that’s what you’re asking for. You’ve made it clear that you don’t want to hear certain predictable pieces of advice or platitudes. Plus you’ve written to me, as opposed to maybe some other person who might be able to offer more in the area of practical advice. That in itself says something.

So after reading your letter, which was very enjoyable — I like the way you have thought this through, and I like the way you express yourself, especially when you note that some people seem to think women age purely out of spite (that was good!) — I went over it again looking for actual questions or problems that I could address. And I found this: “The whole thing scares me and I don’t know how to deal with that fear.”

Now that I can relate to. The prospect of aging scares you and you don’t know how to deal with the fear. That’s a very honest statement. I think it’s a great place to start. It’s a great place to stop, too, if you get what I mean. It’s not really about age, it’s about fear.

You’re dealing with aging very well already. You’re taking care of yourself. You’re thinking through the options it presents and what it requires of you and so forth. But you didn’t say you don’t know how to deal with aging. You said you don’t know how to deal with the fear.

The fear, the fear, the fear. How does one deal with fear? How I deal with fear is mainly I try to identify and make concrete what it is I’m actually afraid of.

Have you ever noticed that a person who is not afraid to state the facts as they are can seem fearless? A person who is not afraid to say I am a socialist or I am a Republican or I am 65 years old and who dares you to do something about it — that that person can seem fearless? What is it about saying the obvious? Well, it makes the obvious obviously less important.

Watch me: My name is Cary Tennis and I am a 52-year-old recovered alcoholic.That’s the truth. You want a piece of me? I had a friend who was a writer who lied about his age in order to seem more interesting. We’re not really friends anymore. I wonder why. I am attracted to people who can tell the truth. It’s a good quality in writing as well — the ability to tell the truth. So I suggest you tell people exactly how old you are and let them deal with it. I mean, do you really want to have a serious relationship with a man who can’t handle the truth?

Another thing I suggest you do about your fear is to make a list of the things that you actually do fear that are related to aging. Make them concrete. Say them out loud: What if a man should reject you when you tell him your age? What would happen then? Would you have to go to the hospital? Would you be unable to speak for a month?

Let me play too: I fear being thought of as an old person. That is too vague. We want to zoom in even closer. And let’s make it you instead of me. I’m not playing anymore. So who exactly would think of you as an old person and how would that affect you? Well, say a man you like were to think of you as too old to date. Say he were to lie to you and tell you he didn’t want to go out with you because he was too raw from a recent breakup, and then you find out later that was a lie and really it was because you were too old for him. What would be the consequences of that? Would that make you lose your job or walk with a limp? Or say that you have a relationship and then the man decides you are too old and breaks up with you and tells you that’s why he’s breaking up with you. What would the consequences of that be? You would probably be angry and upset; you might be more upset than you expected to be. The real fear there, it seems to me, is the fear of emotional pain. It’s normal to fear emotional pain — to fear pain of all kinds. Would it be worse emotional pain if he broke up with you because you were older? How? Because age is something you cannot control?


You are a smart person. You can see where this is going.
What happens when we examine our fears in detail is a couple of things. Either they seem to melt away as trivial, or they lead to more existential things that genuinely do frighten us but which are big universal conditions that we share with all people. It is understandable to fear things we cannot control. That is the human condition.

I could do this all night. The issue is fear.

It also may be helpful to know that you do not have to get rid of your fear. It is OK to feel fear and continue to do what you are doing. There is a book out called “Feel the Fear and Do It Anyway” by Susan Jeffers. I haven’t read it … but it’s a great title, don’t you think? It’s almost all you need to know right there.

The real problem is the fear … itself. Oh, boy, I’m not going to have to quote FDR, am I? Actually, it’s sort of bracing to listen to that famous speech. Maybe before you go out on your next date, just listen to that old guy FDR hammering out his lines. It’s actually, as I said, rather bracing.


My boyfriend is my boss

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Cary’s classic column from MONDAY, NOV 23, 2009

I’m getting sick of being “the editor’s girlfriend”

Dear Cary,

I’m a college student and a reporter for my university’s paper. I’m a good writer — my work has shown up in publications beyond the university, and since arriving here I’ve established myself as “one to watch” in the English department. I really don’t intend to sound cocky, but I’m not affected with false modesty. I have a lot to learn, but I know I have a knack for this.

I’m in a fairly new relationship of about three months, with a boyfriend who so far has been entirely wonderful. We’re both ambitious types with busy schedules and social lives, but we make the time. I think it has been a revelation to both of us just how extraordinary it is to have another person who is truly in your corner.

Here’s the problem — he’s my boss. He’s two years older and is the editor of the school newspaper, while I’m a staff writer. We met outside of the newspaper, and other people are in charge of how much I get paid and where my articles run. We’ve had several serious discussions about ethics, during which we emphasized that I’d never, ever ask him to do me any professional favors, and he would never give me any sort of special treatment. The relationship is more public than I’d like at such an early stage — we’ve both gotten long personal lectures on ethics from the head of the journalism department, and how he heard about us is anyone’s guess.

The thing that bothers me is not the ethical question — I feel like we’re managing that. It’s that I’m entirely fed up with being “the editor’s girlfriend” and not defined as a reporter in my own right. I have never, ever been the kind of woman who would be defined by a relationship — it is extremely important to me that I be defined by my own actions and my own work.

I’ve been doing good work at the paper, and I’m likely to be getting a promotion in the next couple of semesters. But I’m so, so sick of having to hear jokes about my sex life every time one of my stories runs in a prominent place in the paper or I pick up a particularly coveted assignment.

These aren’t serious allegations — the newspaper staff knows that it is not my boyfriend who makes these decisions, and people from outside the staff are only kidding. My friends say to laugh it off, but the fact is that those small successes are things that I earned through a lot of hard work, and the suggestion that I’m somehow trading sexual favors for good assignments truly offends me. I worry that the staff will take me less seriously and that this could endanger my future at the paper.

I know that having a happy relationship and a successful career are not mutually exclusive, but I feel like I’m too young to be dealing with such a minefield. I don’t even know whom to talk to about this — my boyfriend and I are handling it as best we can, but I don’t know how to tell him that although I’m pretty attached to being his girlfriend, I’m getting damn tired of being “the editor’s girlfriend.” I’m not giving up on my work, or on my relationship, I just need to figure out how to reconcile the two.

Her Own Girl Friday

Dear Girl Friday,

I suggest you try to be a little lighthearted about this. Imagine strutting around campus wearing a T-shirt that says, “I’m sleeping with my boss and enjoying it. You got a problem with that?”
Picture yourself walking amid these yahoos with your head held high. Imagine striking them down with wit and glamour and sophistication. Imagine shutting them up and putting them in their place.

Do you feel better?

Keep going with this. Conjure up an image that makes you feel powerful and proud. Make it vivid and real. Draw some cartoons or make a collage. Create the image of the superhero you are. Inhabit her skin. Name this woman. Give her special powers. Keep her image close to you. Appeal to her for strength and guidance.

And know this: Sexism pervades our culture. The assumption that a woman’s achievements stem from her value as a domestic, sexual and romantic companion rather than as a skilled worker is evidence of that sexism.

You know what else exists in our society? Morons. The world beyond your college gates is a nightmare of hulking, mouth-breathing morons. Morons even run newspapers. So be ready. You’re going to be encountering a lot of sexist morons.

So that’s the sociological part of this.

The other part is psychological: By mixing creativity, sexuality and power, you run the risk of incurring deep psychological wounds if things go wrong. By hooking up with your boss, however much you trust him, you have placed your fate in the hands of someone who may damage you, even if he doesn’t mean to.

That is my opinion, but I assume that it is also a fear of yours. If you sense that you are in dangerous territory emotionally, I would agree that you are.

Stuff can happen in such a relationship to shape the rest of your life. Sometimes people make decisions in such circumstances that last for decades. “Oh, he told me I’d be happier if I wasn’t writing, so I quit.” You know, crazy stuff.

How power, sexuality and creativity combine to damage the psyche is complicated. Let’s assume that our emotional responses are rooted in invisible structures formed very early. As a baby, you must be loved unconditionally. You are helpless. You have no vocational skills. You are just a cute, wiggling bundle that eats and shits and throws up and makes noise. You are not a cowboy or a princess. You must be loved and cared for unconditionally. We get older and develop skills, but underneath, our need to be loved unconditionally persists even after we develop great skills and charm and form adult relationships. One area where this need for unconditional acceptance seems to persist most deeply is in the area of creativity. Why is this so?

Could it be because creativity is our one way back to that primal state?

That would be my guess. Betrayal of this creative self reaches beyond personality self into some realm of existential pain and fear that is difficult to find access to. So if you are exposing this fragile, unprotected, raw creative pre-verbal self — the one that cannot protect itself but must be cared for unconditionally — to the upheavals of romantic and sexual relationship, you are in frightening territory. If for instance you were to break up you might feel unconsciously it was because you were not a good reporter. That may sound stupid. But these decisions, we do not make consciously. They are made by this pre-verbal, emotional self that reacts to rejection as if it were an existential threat. So I assume you feel concerned and confused for good reason. You are exposing your psyche to risks that you might not consciously understand.

What can you do? For one thing, you can begin getting assignments outside the school. You can strike out on your own so that there is no question in anyone’s mind how you did it. And  I would suggest, if possible, that you find some ally, a therapist or counselor or older friend, and go through this with that person, checking in frequently, discussing this, asking for protection, watching for ways that you have placed your fragile creativity in danger. If you are in self-doubt, ask yourself why. If you feel like quitting, interrogate your feelings. Honor them but interrogate them. It might be this frightened child who wants to quit. Beware. It’s complex. Keep moving forward.

p.s. You know that Yeats poems that ends, “I have spread my dreams under your feet; Tread softly because you tread on my dreams”? What a lovely and moving poem that is.


A fellow attorney thinks I’m crazy

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Cary’s classic column from Sunday, Jun 5, 2011

Sure, I’m crazy — for him! But I botched my approach! Now how do I wriggle out?

Dear Cary:

I have been following your column for years. I hope you can help me — I need concrete advice, almost like a to-do list on what to do next. I have ruined a wonderful friendship, and I want to repair it.

I am an attorney. My workspace, and all others who are similarly situated, is a cubicle, so there is no privacy. I really like one of my co-workers. He is close friends with our boss and is one of the most respected attorneys here. I wanted to have a physical relationship with him. He said that he found me attractive but did not want a physical relationship for a number of reasons. He repeatedly said that women are crazy. He has absolutely no patience for “out of control.” We managed to develop a fairly close friendship. I started to get too deep. Yesterday I left him a voicemail message saying that I needed to dial back, that he would meet the woman he has been looking for, maybe even this weekend, and that I didn’t want to be in a position of missing my friend when he started spending all his time with that woman, so I was dialing back. He got upset. He said that we were never dating, that the message was the type of message one would get from a girlfriend. I thought I was being honest and self-protective. But instead I revealed myself as being in too deep and like another one of the crazy women in his life (his term, crazy women). I called him on the telephone as we drove to our homes. He said that it was a crazy message. My voice rose. I asked how it was crazy. He said, “Well, you’re the one who left it.” I truly value our friendship. I feel as though I have lost all dignity and revealed my worst (to him), most emotional side. I need concrete and specific advice on what to do. How do I repair the friendship?

Please do not reveal my name.

Emotional Attorney


Dear Emotional Attorney,

Here is some clear, practical advice. Stick your head in his cubicle at your very next opportunity and say, “About that phone message. Just wanted to say. Sorry. I was a little wound up.”

Then he will probably say, “No problem. Don’t give it a second thought.” Or, “That’s OK.”

After he says that, be very careful. You are on your way out now. You are already done. Do not open up another line of argument.

He might say one or two more things. But you are already done. You’ve delivered the message. No matter what else he says, just say something like “Thanks. Just wanted you to know.” Or, “No problem,” and get out of there.

The next thing is the exit. Make your exit swift but not sudden. Make it even. Don’t rush out, but don’t linger. Try to get a rhythm into it, like, in terms of beats, it’s: One, pop your head in; Two, deliver your message; Three, acknowledge whatever he says; Four, turn lightly, in rhythm with your shrug, or your acknowledgment, and walk away with a light, relaxed step.Then settle into your cubicle and start reading a brief. Visualize a soundproof plexiglass wall between you, reaching up to the ceiling. He is not there. You are alone in your cubicle.

This should reassure him. The matter will promptly leave his mind.
Of course, the fact that it will promptly leave his mind is part of the problem. There is a huge issue remaining. It is an issue that, if you talk about it with him, will not settle things but make them more complicated. It would probably be a losing argument. At the same time, it would be intellectually dishonest not to mention it. Feminist advances in pay and freedom were won in hard-fought battles house by house, bed by bed and cubicle by cubicle. So while you may want to keep this huge issue out of the air for professional workplace reasons, let’s just state it for the record: He thinks women who express their emotions are crazy. He’s friends with the boss. So your long-term prospects for professional advancement may well be in the hands of men who think women who express their emotions are crazy.

Maybe you can change their minds. Or maybe you can find another law firm. There are lots of  law firms.

‘Nuff said, OK?

As far as maintaining your friendship with him over the coming months, do indeed “dial it back.” But telling him you’re dialing it back does not dial it back. It ramps it up. That’s what happened with that phone call. It’s one of those paradoxes. The way you actually dial it back is by changing the way you act around him. Visualize detachment. Look at him as though he were far away and tiny, like at the wrong end of a telescope. Speak with him in a controlled and deliberate way. Don’t share your feelings. Don’t ask about his romantic life. Keep your friendship professional.

And one more thing: Don’t call him on the phone from your car. If you find yourself having erotic thoughts about him, transfer them to someone else outside the office — a waiter, or a judge, or an attorney on the other coast you met at a conference.


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Mom says dump the boyfriend or leave home!

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Cary’s classic column from THURSDAY, JUN 25, 2009

We got caught making out and now my mom’s all like you have to break up with him if you want to keep living here

Dear Cary,

My name is V and I’m 18 years old. I have a boyfriend and he’s 18 years old too, but the situation here is that my family has never liked my boyfriend. Me and my boyfriend have been going out for 10 months, and he has always been a good boyfriend to me. The reason my family doesn’t like him is because of the way he talks all ghetto like.

My mom says that he has me threatened and that I’m scared of him, but she is saying things without knowing that my boyfriend actually respects me. He has never hit me or yelled at me, and if he did, I would tell him to watch it, and he’d be like, I’m sorry, babe. Besides that, Friday was his graduation, and after his graduation I went to his house to celebrate. While at his house, I called my mom and let her know I was going to be at his house, and she said it’s OK, she’ll go pick me up.

After a while being at his house, he was getting hot and turned on, so we told everyone we were going to the store, and as we went out the door, he pulled me into the basement and we went in there. We were alone, and let me tell you, I already lost my virginity before that with him, but we weren’t really doing anything besides making out and I did a striptease for him. After a while we heard people looking for us, and his aunt saw when I was slipping my dress back on and started to yell at me and told me to get out of her house. By the way, my mom didn’t know anything about me not being a virgin. So as I was putting my heels on, his aunt told my mom how she found us. My mom was upset, very, very upset after that day.

She hadn’t said anything to me up until yesterday, when she told me to sit down in the living room and started talking, and her rules were:

Break up with your boyfriend and you can live at my house under my rules and keep your studies at the university, or
Leave the house. If you’re not willing to leave your boyfriend, then go live with him and lose your studies.

And honestly I don’t know what to do. I need help because I love my boyfriend to death and he’s willing to help me out if I go live with him. As a matter of fact, he’s been looking for jobs already, and he talked to his aunt, and she said it is all right with her if I go with them, but I’ll have to get a job, and that’s OK with me.

My problem in deciding between one or the other is that my family has always been everything, but for some reason I have felt like they have been turning their back on me and they don’t want to listen to me. My mom is mad at me. She says she’s disappointed in me, and I’m afraid that if I stay here at my house that she’s going to keep on bringing this situation up, because my mom tries to control my life all the time. She says if I live under her roof, I do what she tells me to do. I have no opinion and no say in anything, and I am tired of them deciding for me.

I have already made a decision to leave my house and learn to be an independent woman on my own, and go live with my boyfriend and just make my life already. I am conscious that it is not going to be easy, but I just want to be with my boyfriend. To tell you the truth, I want for my family to at least get along with my boyfriend. That way I won’t have to leave. I really do not want to leave my house because of my little sister. She told me last night crying that she doesn’t want me to leave because she can’t sleep without me being in the room with her. I know I did things wrong, but in my opinion my mom is taking things way too far.

All I’m looking for is for someone to tell me their opinion on my situation and to help me out. I am really seeking some help.




Dear Confused,

I think you should stay at home for now until things can get sorted out. Ask your mom for some time. Promise to stop seeing your boyfriend for two weeks or a month while you sort things out. That will give her time to cool down.

Then tell your boyfriend the only way you can still keep seeing him is if he will go, on his own, to talk to your mom. He’s got to apologize and impress her that he is a gentle and honest man. He’s got to humble himself before her. But he’s got to be honest with her, too. He can’t snow her. If she senses that he’s trying to deceive her, or charm her, or sweet-talk her, she will become hardened to him. It’s got to be genuine. He’s got to say that he likes you very much, enough that he is willing to make some sacrifices in order to continue seeing you.

Now, you can’t get this all done in one conversation with your mom. So just tell her that for now, you want to stay at home and you’re having a “moratorium” on the boyfriend.

Here is the important thing: You have to have some flexibility and patience. When families suddenly break apart over something like this, it hurts everyone. It hurts you, it hurts your mom, and it hurts your sister.

So you need to use conflict resolution. If you can slowly resolve the conflicts, maybe this can be worked out to everyone’s benefit.

There are a lot of emotions involved. Your mom is trying to protect you, and you are trying to grow and be your own person. That naturally creates conflict. You have to learn to do some negotiating with your mom.

In negotiating with your mom, you have to have some things to offer her. What do you have to offer? Make a list of all the things you have to offer her if you stay at home: You can help take care of your sister. Staying at home will make your sister happy. You can clean and cook at home. You can be with your mom and keep her company. And you can stay in school so you can get a good job.

Your mom doesn’t really want you to leave. She wants you to stay in school. She wants you to stay at home. But she is trying to be a good mom. And she is trying to feel like she has some power over what goes on. So give her some power. Give her what she wants. But do that in a way that gives you some rights, too.

Now, after your boyfriend talks to your mom, you will want to see what she says. If you want to keep seeing your boyfriend, you don’t want to have to do it in secret. So you’ll have to figure that one out. If he can’t be persuasive, maybe his aunt will have to come talk to your mom as well. And if you’re going to keep seeing him, there will have to be some limits. Your mom won’t want him going into your room, and she won’t want you sleeping at his house or spending the night somewhere. You can guarantee she won’t want that. But if he approaches her on his own, and apologizes for what happened, and impresses on her that he truly cares for you and wants what’s best for you, she might agree to let you keep seeing each other.

You have this on your side: She doesn’t really want you to leave. She wants to keep her family together, but she wants some control and some respect. So this situation can be worked out. It doesn’t have to end in bitterness.

And don’t forget your little sister. You can “lobby” your little sister: Tell her that you very much want to stay at home, and that you just have to work things out with your mom. Don’t necessarily try to get her to take sides, but just be honest with her. In a pinch, she can tell your mom that she, too, really wants you to stay.

The most important thing at this crucial point, whatever happens, is this: Stay close to your mom and to your sister. Stay in school until you have a useful skill and you know how to get a job and support yourself. And don’t count on your boyfriend. I’m sure he’s great, but things do change. At 18, a year is like a lifetime. Things could change.

So the best solution is for you to try to negotiate something with your mom where you can live at home. You’ll have to give up some things, but so will she. She’s angry right now and being overly rigid. Show her you can compromise, and maybe she will accept your solution.

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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?


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.


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


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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