By Baila Sebrow


I’m 32 years old and was recently set up with a gentleman who is 38. We went on three dates and each date was special and different. (I have gone on many dates with various people, so I feel confident in saying there was something different and special about these dates.)

I grew up with observant parents and kept strictly kosher and Shabbat. I never had a formal Jewish education, though, so anything I learned was through family and friends. As I entered my early twenties, I became a bit less observant; however, Judaism is still important to me. I am with my family for every Shabbat dinner and lunch and major holidays. I keep kosher but will eat vegetarian food at non-kosher restaurants, and I observe Shabbat on some level but will use my phone and car to see family and friends. I have gotten to a place in my life where I feel that I can incorporate religion and make it count for me, without being on either extreme.

Back to the gentleman I was set up with: He grew up completely secular but is now exploring the world of spirituality and religion. On our first date, we had a great time and there seemed to be a connection. It was also very much an interview, similar to Orthodox dating. He asked questions such as how many children I want, if I want my kids to go to a Jewish school, and if I’d be open to eating at only kosher restaurants in the future. On the topic of Jewish education, I explained to him truthfully that I don’t spend much time thinking about it; however, my initial reaction is that Jewish education is certainly important, but I don’t think children should only be exposed to Jewish people because the real world is not all Jewish people. I understand that one may interpret that as “No, I don’t want my kids to go to Jewish school,” but I see myself as an extremely open-minded person, and not everything has to be so black-and-white, nor am I set in my ways. So, for example, the compromise could be that the kids go to Jewish school but are involved in extracurricular activities to expose them to people with different backgrounds. He also brought up the idea of being shomer negiah, something new to him, which is not exactly what I had envisioned for myself, but I told him that I’m intrigued and absolutely open to trying it.

After I made this commitment, he seemed to be a little flustered and said that this is going to be “very difficult.” Nonetheless, I assured him that we don’t need to spend much time on the topic, and we can simply give it a try.

During our three dates, I found him to be extremely attentive, caring, curious, and a G-d-fearing man. He embodied a lot of qualities that I have been searching for and there really wasn’t a box that he didn’t check for me. He mentioned throughout our dates what a nice time he’s having, how relaxed he feels around me, and that he is attracted to me. Everything seemed to be really great, but he called to let me know that he doesn’t feel that we should continue seeing each other; it was nothing I said or did, but more about him and the spiritual / religious journey that he’s exploring.

It has now been two months since we spoke, and I think about him every day. It’s been a hard pill to swallow that while there was such a strong emotional connection there, religion may have been what ended it. I feel that I wasn’t heard when I said I will keep an open mind to religion and that he didn’t quite seem to do the same in terms of compromise and negotiating where and how we can fit religion into our lives so that it works for both of us. It’s hurtful that someone can see me in this light when Judaism has been a part of my entire life, and to be judged by someone who decided to become religious much later in life.

Is this someone I completely let go of and move on from, or is there any kind of hope in making this work?


In layman’s terms, it sounds like this gentleman contracted a case of “cold feet.” When two people are in a relationship that appears to be headed in the direction of getting serious, and one backs out, it is usually because there was strong enough doubt to cause fear or hesitation.

Yet, for those who are professionals in dealing with issues in dating and relationships, the reality is that “cold feet” has a motive behind it. In many cases, the real drive to end a relationship never gets detected, and relationships that for all intents and purposes should have worked, end instead. When it’s the result of a misunderstanding or something assumed, the fracture of such a relationship is tragic.

There are those who believe that cold feet could be a fear of commitment. In such a case, the person will always look for a reason to get out. Meaning, he or she has a history that keeps repeating itself, with the same script but different characters. Since you don’t make any mention of his prior relationships, I will go with the premise that in your case his backing out has nothing to do with fear or plain refusal to commit.

It appears that you are both in different places with regard to hashkafic outlook. You grew up observant, but over time chose to be a bit less vigilant; nevertheless, you have never given up enjoying the spiritual aspects of observance. In fact, you make it a focal point in your life to spend all the Shabbat and yom tov meals with your family. The way you describe your steadfast tradition is beautiful and touching. You are surely a true inspiration to many who have veered to the left but dropped rituals and their connection to family as well.

The gentleman you dated grew up secular, unlike you, but is now discovering what it is to be observant. That, too, is deserving of many accolades. However, since you are both coming from vastly distinct places, it will ultimately have significant impact on where you each decide to plateau on the level of hashkafic stability.

You don’t mention how you met each other in the first place. Oftentimes, people who have been raised observant but with time became less religious are commonly matched with those who are not religious but express the desire to lean in that direction. I wonder if that is what happened here. I can understand the philosophy of such a viewpoint, in that it is assumed that one will help balance the other, but, realistically, the couple will be dealing with compatibility issues regarding hashkafah from an intellectual standpoint. Although you are ready to make any compromise necessary in order to have a life with him, he doesn’t see how it could be carried out, because it is possible that he may not want to put in his share of the work.

It would be easy to tell you to move on, but the fact that you took the time to write to me is indicative that you want to do whatever is possible to get this man back into your life. You need to first ascertain if religion was the real reason he ended it and not just an excuse. People are not always completely honest when they break up with somebody. The excuse they give is not necessarily the true cause, because they either refuse to share the truth, or it may be that when a person makes the decision to end a relationship, he may no longer feel compelled to give a full explanation.

Please bear in mind that whatever is really going on could be something entirely different (nothing to do with religion) that you cannot change, or that he has another mental image of what he is looking for in a life partner. I understand that you have grown to emotionally connect with him, but the fact is that you spent only three dates together. This was not a long relationship, nor was any promise of a future together made by him. It is not unusual to go out with somebody three times and it ends there. If it turns out that this is the case, you will have had all the closure he is obligated to give you, and as disappointing as it is to you, you will have no choice but to accept it.

However, if his sudden rejection is really just a misunderstanding, then not doing something that could straighten it out and mend a relationship that has good potential would be tragic. So let’s focus on that possibility.

Levels of religiosity play a huge part in the harmony of a marriage and family. You are comfortable with where you are holding in observance, though you are willing to adjust to possibly doing much more, as I understand in your willingness to eat at kosher restaurants only and send your future children, G-d willing, to a Jewish school. Not only that but, you are even prepared to observe the mitzvah of being shomer negiah. Such commitments are worthy of tremendous praise and it demonstrates that you are a person of high integrity who will make a selfless and devoted spouse.

When you say that he became “a little flustered” and then explained that it would be “very difficult,” he might be talking about himself. He may not be so sure that he wants to go that route. He may be dealing with uncertainty and confusion about religion and where he really sees himself in the future. Or perhaps — and this is not so uncommon among ba’alei teshuvah — he was specifically seeking to date somebody who is way more to the right. For example, as a shadchan I have had requests from women who are ba’alos teshuvah to be introduced only to a rabbi. I frequently get requests from men who are ba’alei teshuvah or still exploring religiosity and spirituality and dress very liberal that they only want to date a woman who will wear a sheitel and dress as modestly as a Bais Yaakov graduate. An ordinary frum man or woman is just not good enough for them. They want the whole nine yards, so to speak. Why they make such requests could have something to do with proving to themselves and others that someone who is more stringent in observance finds them desirable for marriage, or simply because that is what they are attracted to and aspire to become one day. There could be other motives that are more personal, too.

This gentleman may need reassurance that the fact that you were raised Orthodox and veered to the left means that you understand both sides of hashkafah and you can cite various personal experiences. There are cases where the relationship between a ba’al teshuvah and one who has been religious from birth does not work out because they are both coming from different places in life and neither is willing to be understanding of and patient with the other.

It might turn out that even though a couple might be right for each other, the timing is wrong. This gentleman may still be trying to figure things out for himself. I know you feel judged, but please don’t look at it that way, because when people date, in a sense they are questioning their own judgment. Ultimately, you do not want to be with a man who doesn’t appreciate all you have to offer.

To sum it up, contact him and listen to what he has to say. If you feel he needs the support that you will be there for him and move at his pace while he’s on his journey of observance, give that to him. But if he remains unwavering in his decision to no longer date you, then you owe it to yourself and your own dignity to let it go. He might decide at a later date to reconsider and revisit the possibility of trying again with you, or maybe not.

I will leave you with this thought. Rejection does not mean that that you aren’t good enough. It usually means that the person was not a good fit for you, and there is somebody more compatible who is deserving of the special young lady you are. 

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. She can be reached at Questions and comments for the Dating Forum can be submitted to


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