By Baila Sebrow


I’m a mature man who has been dating for many years. Every woman I ask out will say that I treat her like gold. I take them to museums, concerts, out to eat, etc. I am very open-minded, and I even date women my own age, from all backgrounds, and of all different looks. The problem has been that I get really taken by someone early on, and I think that this is the person I want to marry, but then I get cold feet. This keeps happening to me. All the women I date are just wonderful, and I wish that I could go ahead and marry one of them. It’s funny that each woman is better than the next. There is nothing wrong with any of the women I date.

Word on the street is that I’m a player. I don’t mean to give that impression, and I don’t want to hurt anyone, but it ends up happening anyway. I’m ready to give up on dating if it hurts people and causes so much trouble. What do you think I should do?


I am not sure why you have developed a reputation for being a player. As long as you treat each woman you date with respect, you shouldn’t be compared to a player. However, treating someone like “gold,” as you say, may not always mean meeting expectations about how a relationship is carried out. I am not saying that you don’t respect the women you date, but it could be that those you date or are surrounded by have different perceptions about what a player means. It is also possible that you developed that reputation because you date a lot. Oftentimes people are labeled negatively, based on an inaccurate assumption.

Delving further into the term “player,” you say that when you are taken by someone and presume that she is the woman you want to marry, you then get cold feet. How soon after you date them do you get cold feet? Is it after a few dates, or do you establish a long relationship with someone, and at the eleventh hour, you back out? And how quickly after one relationship ends till the next one begins with the same finale? All those questions can only be answered truthfully by you.

Let’s talk about the issue at hand that is currently bothering you. From what I gather, you are ready to stop dating until you can figure things out. I agree with you. If you find that history repeats itself, where you feel that you have no control over the outcome, then it is best that you take a break for your own good as well as for the sake of any woman you might potentially hurt.

It’s interesting that you find each woman better than the next. There are men who end relationships just as you, but in their case they do so because they find a fault within her, real or imagined. But the outcome is still the same. You are, therefore, in a more complicated position, because you have no clue why you are rejecting women. You have thus far been unable to identify the reason.

Most men who find a wonderful woman will be happy to marry her. What I find perplexing is that you find all your dates to be high-quality. You also say that you are enamored by them early on. Could it be that you place them on such a high pedestal that it is impossible for any human being to remain on that level, and when you discover that they are not as you imagined them to be, you then end it?

There could also be something else going on. And that is the “kid in the candy store” complex. A kid walks into a candy store and cannot settle on one candy, because there are so many delicious choices. Similarly, when people receive a gift box of chocolates, it is not uncommon — even for adults — to want to take a bite out of each. It would be a good idea to discuss this with a therapist, because it sounds like you really do want to get married, but you are unsure how to bring yourself to that level.

I’m going to go out on a limb and give you something else to ponder. There are singles who date people in whom they find good qualities, but they just don’t feel a connection to the person they are dating. You state that you are open-minded. Being open-minded is a good thing. However, even a good thing can be overkill. I am always suspicious when a mature person tells me, “I can date any age, personality, look, intellect, hashkafah, etc.” At the end of the day, that mindset usually ends up working against them. There is no way that a person is compatible with everyone he or she dates. As time goes on, and you get to know these women, it may be that you are recognizing the dissimilarities. And when it comes time to make that commitment, you might get scared, or get “cold feet.”

That said, it would be a good idea to reevaluate what type of person would be most compatible with you. But before you do that, take a good introspective look at yourself. Be honest about who you are and what you feel you can bring into a relationship. Based on your assessment, focus on the type of woman you believe would be the correct fit for you.

I also get the feeling that when you meet someone or you receive a suggestion, you might be hesitant to decline, just in case it may work out. Reexamining yourself and rebuilding your requirements should help narrow down the list of people you would have agreed to date in the past.

With whatever is going on, I sense that you are a laid-back type of person. There are times when such personalities do not necessarily make the effort to find out as much as they can in the early stages of dating. They think the information will somehow come through with time. This is why I frequently recommend that although it is important to have a good time on a date, also bear in mind that the first few dates should be treated like an interview. That should not be confused with turning a date into a question-and-answer session. A good idea is to tell your date a little about yourself, and see how she responds. That usually opens the line of communication, where the other person is eager to share his or her past and present. And when people feel comfortable in the other person’s presence, they tend to share more than they initially planned.

If your date is not that open to talking, you may need to ask direct questions. Ask the questions to which the answers will be significant to your life. You may find out early on, after the first date or two, that the person is incompatible with you, sparing you from dragging it out further.

I will point out that there are two important elements in a marital relationship that can have a huge impact on the union. One is financial, and the other is spiritual. I say it in the same sentence because both have the potential to make or break a relationship. Lifestyle habits in both those areas require mutual understanding. When one partner is a spendthrift and the other is frugal, that has been the cause for much disharmony. And even how one envisions money spent is important. What one person may think is important to purchase, another may feel is frivolous. With regard to spirituality, the non-spiritual partner will feel that he or she is on a different wavelength, while the spiritual person will feel a strong disconnect with the non-spiritual.

One’s goals in married life and plans for the future are high on the list in deciding whether that person is right for you. And if you find out that what your date wants or expects is not on board with your thoughts on the matter, do not assume that she will change her mind or that you will get her to change in any way. Shared ideals are part of building a healthy foundation with someone.

An example of an aspect where you don’t need to be similar to one another would be the viewpoint that if you are outgoing then you need someone just like yourself. In fact, some of the best relationships are where one partner is more extroverted than the other. It’s almost as though they help balance each other out.

The tips I am giving you are to help you eliminate people who may not be compatible with you in the early stages. Ending a would-be relationship early on is less painful for the person rejected. At worst, it’s a feeling of disappointment. That is better than the pain of a broken heart. 

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. Questions and comments for the Dating Forum can be submitted to


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