I’ve been dating for quite a long time and I can’t seem to agree to get married. All the guys say I’m the nicest girl they ever took out or dated, even some guys I dated for several months. I’m very considerate of my dates. Sometimes I even bake cookies for them after a few dates and I always call them back when they call or if they text. I never play games by not texting back, no matter how busy I am. Shadchanim consider me to be very open-minded. I also date guys up to nine years older or a few years younger. I’m also open-minded about hashkafa. I don’t care if a guy wears a black hat or if he’s a YU type of guy.

The problem is that I lose interest in them. In the beginning, I get very excited to meet a new guy and everything seems perfect, and it’s not that it always gets bad. There were times when I thought I could actually have married a guy. But then I got cold feet. The truth is that there have been many guys I could have married; they were all so wonderful. Then I meet another guy and he is great too, and sometimes better than the previous one. I don’t want to hurt anyone, but it ends up happening anyway.

I’m ready to give up dating if I keep hurting guys, even though that’s not my intention at all. What do you think? My brother (who’s married) thinks that I’m the female version of a “player.” I’m not sure if he’s making it up or if that’s what people are saying about me. But what I do know is that people think I’m either too picky or that I’m not really serious about marriage. The fact is, I do want to get married. Just to mention that I’m in my early 40s and still want to make sure I have a good reputation.


I don’t think you should concern yourself with what people think or say about you. According to the way you describe yourself and how you communicate with guys via text or phone, it sounds like you are truly a lovely person. Other than what your brother is telling you, it does not sound like your reputation is suffering because you get cold feet when it comes to getting serious. Quite the opposite, you stated “all the guys say that I’m the nicest girl they ever took out or dated.” I believe that your brother might be projecting his fears that your reputation could be potentially impaired if your patterns of dating continue in the same manner.

Your dilemma, according to your perception, is not that you are going out with the wrong type of guys, or that the guys you date have expectations of you that you can’t meet. On the contrary, you express being open-minded in various areas, including age and hashkafah. That is huge, and not as common as you might think. Moreover, you seem to be their match too, at least on paper. You have even dated some for an extended period. It is interesting to note that people who date a lot are immediately accused of being picky and not serious. Though that may be true for some, it is not necessarily always the case, as you seem to convey.

You talk about getting “cold feet.” It sounds like what keeps happening is that you really like somebody to the extent that you would presumably marry them, and then you back out. Typically, how long after you date a guy do you get cold feet? When it’s not after a few dates, but after you establish a long relationship with somebody, do you back out at the eleventh hour, meaning right at the point where you anticipate a marriage proposal? And how quickly after one relationship ends till the next one begins with the same ending?

I would like to delve into what exactly could be bothering you, and how do you foresee changes to affect the outcome? From what I gather, you are ready to stop dating altogether until you figure things out. That is not a bad idea. In fact, it’s a healthy alternative for longtime daters to do. Removing yourself from the situation for some time can give you the chance to view yourself from a more neutral stance than when running from guy to guy. If you find that history repeats itself over and over where you feel that you have no control over the outcome, then it’s best that you take a break for your own good as well as the next guy, who for all intents and purposes, will likely get hurt.

You say that sometimes the new guy is better than the one before. What does that mean to you? To me it comes across that deep down your gut may have been (in certain situations) telling you that although the previous guy may have checked all the boxes of compatibility on paper, you had a hunch that something was off. That does not necessarily mean the guy was bad, but it could mean that you felt a lack of compatibility in a significant area.

Although every circumstance is different, there are cases of single men and women who end relationships either because they find a real fault in the person or deep down, they don’t really want to be married. Yet, the outcome is still the same. You seem to be in a more complicated position because you seem to want to be married, yet you have no clue as to why you are rejecting seemingly good marriageable prospects. In other words, you fail to identify the reason.

Most of the complaints I hear from singles are that they wish they could find a great guy, and when they do, they would immediately marry him. What I find mind-boggling is that in your opinion, all your dates are great guys. What is it about them that in the beginning they seem so great, but after a while, they are not as great as you first thought? That is commonly seen amongst those who place the new people in their lives on such a high pedestal that it is impossible for any human being to remain on that level. When they get comfortable with you, you discover that they are not as you imagined them to be and then you end it. The new person seems better than the previous one because the previous one is no longer the idol you thought him to be. Does that make any sense to you?

I sometimes use the candy store analogy as it pertains to dating. A person walks into a candy store filled with an array of candies to choose from. He or she can only have one choice amongst the myriads of options on display. There are those that will automatically lay eyes on one candy, purchase it, and be done. Then there are others who cannot settle on one particular candy because there are too many delicious options.

I noticed that you disclosed your age at the end of your letter rather than at the beginning, and I get why you did that. It likely makes you uncomfortable to state your age right off the bat. Not every single man or woman finds the one they want to marry at a young age. People are complex, and what works for one does not always work for another. It’s not just about finding somebody with top-notch qualities. There are singles who date people who have all those qualities, yet they don’t feel a connection to the person. This has nothing to do with being open-minded. There is no way a person can be compatible with everyone they meet. As time goes by and you get to know a guy, it could be that you recognize unsuitability in the person. And when it comes to making a commitment, you may get scared that it won’t work out, which is commonly referred to as cold feet.

Please re-evaluate what type of person would be most compatible with you. It can’t be that every guy is so wonderful. It is okay to not feel that way sometimes. Be honest with yourself about who you are and what you feel you can bring into a relationship. And consequently, the type of man you believe would be the correct fit for you. It is also okay to decline a suggestion every once in while too.

It might be a good idea to ask vital questions early on after the first date or two, rather than waiting until later to discover that the person is not compatible. Find out what their future goals are in life, what they expect from their spouse, and if you are on the same page. That does not mean there can’t be any dissimilarity between you and a guy to have a happy marriage. I’m talking about things that are deal-breakers for you. What you are going through might involve excluding people early on that have certain characteristics that would not work for you in the long term. I would also like to recommend that you reach out to a mental health professional to help you identify and understand your struggles more clearly. n


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. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at Bsebrow@aol.com.



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