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

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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.

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