Dear Carol,

When I first got to college I was horribly shy and introverted, and had terrible social skills. Then I went through a period of intense personal growth, including encounter groups, and became more comfortable with emotional intimacy than casual social interactions. I did not have my first girlfriend until I was thirty. Later I had years of fruitless dating, even though I had opened up and become much more socially competent. Despite my improvements I was still fairly passionless, lacking in vigor: a bland and passive nice guy with marginal self-confidence whom women did not find romantically attractive. I had so much love inside to give, so much sensitivity, caring, and empathy, but could not demonstrate these well on a first or second date. (This failure to connect romantically has not precluded good platonic friendships with women.)

Last year I developed a wonderful Internet relationship with an exceptional woman in another state, who in many respects was the woman of my dreams. By the time we met, we were very close friends, as we had been honest and open with each other. We quickly developed a wonderful romance. Unfortunately, that ended by her choice after six months, even though we still remain good friends. She is now with another man, and deeply in love with him.

This relationship triggered tremendous personal growth in me. I am now far more self-confident, open, and relaxed than ever before, even a person of some passion and sensuality. I am genuinely more attractive to women now. Still, here I am at age 43, with only two relationships under my belt, neither of which was long-term. I know I have good relationship skills for a person with so little experience in emotional intimacy. I am now finding that women my age want to know why I am still single, and whether I have had a long-term relationship. They know from experience about common male failings, and are on the lookout for such.

Yet my background is misleading. One might think that being single, I’ve been a stereotypical playboy, hopping from woman to woman. Plus, my lack of a long-term relationship suggests a fear of commitment or a lack of relationship skills. My problem has not really been with maintaining relationships. Rather, I have not been able to make that initial romantic connection to women, except for those two times when we were friends first. So I feel haunted by my past, and dread those questions from women. I have already been rejected more than once on the basis of my past, and I fear I will not be given a chance to show how well I can do once there is mutual trust and affection. My last relationship was the kind of miracle that I cannot count on happening again, even though that wonderful woman is now cheering me on and coaching me as I date once more.

All recriminations aside (and believe me, I have blamed myself so much for my past), how can I move forward into another relationship? How can I get past the initial barrier of suspicion, so that I can show what is in my heart, and show how caring and sensitive I am? I feel as if I’m in a Catch-22, as if I need to first have a long-term relationship to prove I can do so, before I will be allowed to have one! I don’t want a short-term fling. I want to connect to an ethical woman of quality, intelligence, compassion, warmth, and passion. Yet these are the women who seem to be scared off by my past! I should add that I have learned to be a little reticent on this topic, to not reveal too much too soon, yet how can I lie or evade a direct question without being unethical or looking evasive? The truth looks so bad, if I give it in response to a direct question. What do you suggest I do? –Leo

Dear Leo,

Just about anything can put the kibosh on a potential relationship–sometimes the wind changes and a likely mate never returns another call. So you need to go about your life in the ways that interest you most, coming in contact with as many great people as you can and presenting yourself honestly in spite of your fear that your past will always get in your way. The lover you seek will understand that you had a horribly painful and shy youth (perhaps she did, as well) and that for a while circumstances and chance pointed you in directions other than long-term relationships. Look at it this way: Your growth has been hard-won. It’s precious. Your history can, if you are honest about it, lead you toward the people who will be most likely to respect it–and you.

This doesn’t mean you should tell the whole story of your life on the first date (that can sometimes be overly intimate, and it’s often better to let the getting-to-know-you process unfold a little more slowly). But don’t evade the truth–as you suspect, women will note the evasion and think there’s something fishy going on. Try to address their questions briefly and nondefensively, tell them you are glad to talk about your history in more detail if they want to know about it, and move on. Some women will judge you anyway, but look at it this way–if you became involved with them they’d soon start to judge other things about you, too. Now that you know you have what it takes, don’t let your fear stop you from connecting with wonderful people. Having overcome the kinds of barriers you have overcome is something to be proud of, and the irony of your situation is that your fear about revealing your past threatens to become as much of a barrier as your lack of social skills used to be. Don’t let that happen.