I'm a babe, a total catch -- so why am I alone at 39?

I just spent two weeks crying about my best friend's wedding dress.

By Cary Tennis
Published January 23, 2007 11:37AM (EST)

Dear Cary,

I'm a 39-year-old black woman who has had only one serious romantic relationship in her entire life. It lasted just six months. I never dated in high school, had a few "hookups" in college, and had just that one relationship when I was 24. I've spent the last 15 years piecing together a rather pathetic "dating" life with men I've met through either online/newspaper ads or the few blind dates I've been set up on. I continued to go out with the majority of these men for a little while because I was lonely, not because there was any kind of real attraction -- mental or physical -- on my part. The few men I actually was attracted to did not want any type of committed relationship with me, but stayed around for the sex. I've spent most of my 20s and all of my 30s basically alone.

I'm funny, smart, charming and dynamic. I'm complimented almost daily on my looks, so I know I'm not ugly. Oddly, men smile at and flirt with me all of the time at my job, in bars or on the street, but for some reason, they never ask me out. I've tried to take matters into my hands many times and instigate something with them, but they never take the bait. I usually find out later that they have chosen to pursue someone less attractive and much dumber. I've tried everything I could think of to be appealing and attractive to men without seeming lonely and desperate. Nothing. No one I know can figure out why I'm still alone after all these years.

Even though I have sometimes felt sad and dejected about my situation, I've tried to deal with it the best I could. I never let being alone stop me from living my life: I finished my master's degree, bought a house, traveled widely, learned three languages. I volunteer my time regularly. I have a career I enjoy, a wonderful family and a dear best friend. I wear nice clothes. I drive a very nice car. I have a good life in many ways. I thought I was handling, even thriving in, my singleness ... then I got a kick in ass.

My best friend announced two months ago that she is getting married to a man I introduced her to. I genuinely feel happy and excited for her. She has had a succession of bad relationships, and this man is a true Prince Charming. I am in the process of helping her plan for her wedding, which I am glad to do.

One night, after a lengthy, but funny discussion about wedding dresses, I hung up the phone with her and ended up having what felt like a complete breakdown. I haven't stopped crying for two weeks. I'm no psychologist, but I am sure that her upcoming wedding has probably triggered all of the feelings of rejection and sadness I feel about my stunted love life. I am overwhelmed with despair and grief, but I've been trying to hide it because I don't want to spoil her happiness.

In between the sadness and grief, I feel intense regret and anger. I regret that I'm almost 40 and the years are slipping away, but I have yet to participate in even one long-term relationship with someone I truly care about. I'm angry that people with less stellar qualities than I have seem to have no problems finding mates, while I spend all of my time alone.

Intellectually, I know that as a black woman it is a statistical fact that I will have a harder time finding a suitable mate than women of other races. I also know that finding love is sometimes based on just plain luck. Many people have and will die alone. Yeah, I get it. Yet, it doesn't make it easier to handle. I want to believe that I may eventually find the true love of my life, but my hope diminishes daily.

With time, I may eventually get over this and get back to living my life as I had before. Right now, though, I just want someone to say something that will ease the intense pain I feel. When I even hint at my sadness to friends and relatives, I hear the same bullshit, "Relax, it will happen when you least expect it." Maybe, but what do I do in the meantime? How do I continue to live my life as meaningfully and as joyously as possible when I feel nothing but a constant dull ache in my heart? How can I bear loneliness that is so deep that I sometimes believe it will drive me insane?

Alone for Life?

Dear Alone for Life,

You are doing all the right things and they aren't working. So why not try doing the wrong things?

The soul is full of contradiction and darkness. So it is always possible that when we are doing all the right things, our soul doesn't have its heart in it. It wants to misbehave. It wants to do the wrong things.

With apologies to all men everywhere, let me speak for men for a moment -- at least for the men who might seem right for you and who yet do not seem to be interested.

We men are filled with longing and things that don't fit -- guilt about blunders and lies we have told and failures we have brought about. Most of us are a mess is what I'm saying. And we're looking for a home for our messed-up selves.

Everybody is happy to house our goodness. That's no problem. And in our professional lives we are more than happy to be good. But who will house our darkness? Some homes are too shiny and they scare us; we don't know where to put our feet.

So yes, we're intimidated, if you want to call it that, but I don't want to call it that. Intimidation implies a contest between two people who are trying to outdo each other. That is precisely what a relationship is not about. A man isn't so much intimidated by a brilliant woman as just plain uncomfortable because there's no place for him to put down his ratty old bag of moldy paperbacks.

Oh, sure, we want to excel. But the desire to excel is fraught with guilt and fear: We do not want to fly too high, like Icarus. As a person for whom it is important to excel, you must know this well.

So what about your dark side? It is our dark selves for which we seek a home in a relationship. It may be that while men admire everything in you that is good, and find you attractive and would like to be with you, their dark side wants a home with someone who is -- not necessarily dumber than you -- but more openly flawed. Vulnerability might be another word for it, or visible hunger, a genuine, quiet, sad, compassionate hunger. Or even perversity -- not sexually, but perversity in the sense of being truly angry at God, of not taking it anymore, of feeling that you are genuinely fucked, of feeling the tragedy of your fate and accepting the tragedy of the fate of others. That's what many of us are looking for: We are looking for a home for the part of ourselves that is like the part of you that has been crying for two weeks. That is the dark part of you that we respond to. That is probably the part that you feel is least attractive, the part of you of which you are most ashamed. But that is what we long for: We long not for your brilliance, but your humanity.

So does this mean that brilliant women must dumb themselves down?

I do not think that is what I am saying, though if revealing your raw humanity seems dumb to you, then perhaps it is. Admittedly, I am the one who asked to speak on behalf of my gender, yet only as a corrective: I do not really think this is about gender or race. I think this is about excellence fatigue, the heaviness of Icarus.

So how would you feel about being loved simply because you are hot, hot, hot? Could you live with that? And what if the man who loved you just because you were hot, hot, hot was not able to meet all your requirements 100 percent? Could you still be loved by a man who has his own set of flaws?

I think there are plenty of men who will love you in their way. Why not let yourself at least be loved, even if that love is flawed?

Why not try being bad for a while? There is much about bad that is very, very good.

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