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.

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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.

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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,

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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.

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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.

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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.

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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.