By Baila Sebrow


I am not so new to dating. It’s been about five years, so I pretty much know most of the eligible guys out there. For the record, I consider myself modern Orthodox and very spiritual. Recently, a shadchan suggested a guy who is yeshivish, but not the typical kind. He watches TV and is worldly. I agreed to give it a shot. We had a great conversation on the phone, and we set a day and time for the date. He told me we would go to a lounge to talk, and I was really OK with that.

At the lounge he asked me what I wanted to drink; I asked for a diet soda, and he ordered the same. The bill came out to $12 plus tax, and he asked the bartender why the bill was so high for two small sodas. The bartender explained that it’s $6 for a drink. This guy made faces at him. We then took our drinks and sat down to talk, but he was still complaining about how much they charge for a soda, so I changed the subject. We then had a great conversation and we got along so well, even though it bothered me that he had complained about a $6 soda.

The next day the shadchan called me to let me know that the guy wants to go out with me again. I told her what happened and said that I don’t want to go out with him again. She explained that he just got divorced (he doesn’t have his civil divorce yet) and he doesn’t have much money now because when he was married, he first learned for a few years and then worked for his father-in-law, but now his father-in-law kicked him out. I see this as a long-term problem. He never went to college, he has no degree, and he has no money. The shadchan thinks I should give him another chance, but I don’t want to. Am I wrong here? Is this something that happens in the more yeshivish circles? I never had that when I dated modern Orthodox men.


When it comes to choosing who to date, nobody can tell you that you are wrong or right. A shidduch is a personal decision. To me it sounds like you are not judging him on the basis that he didn’t take you out to a nice meal in a restaurant. On the contrary, you were fine with going to a lounge for a drink. Your concern is that he complained about the $6 charge, something he never should have done in your presence, and certainly not to the extent that he did. That was way out of line. The way you described his reaction to the tab makes it sound like he doesn’t have much control over his emotions when he is disappointed.

Your second issue is with regard to his finances. We all know that parnassah is determined by the One Above. However, the fact is that he is in the midst of a civil divorce and you don’t know exactly what’s going on. The likelihood is strong that he will remain financially strapped for quite a while. To make matters worse, whatever job he had until now, working for his ex-father-in-law, is no longer an option. Even if he were to try to get another job in whatever field he is knowledgeable in, I doubt he will get a good reference from that man, and depending on what he did before, his lack of a college degree might hinder him further. That is a serious concern.

With all that said, I still must stress that one of the huge mistakes that dating women often make is assessing a man’s eligibility based on how much he spends on dates. There are plenty of cases where men who have spent excessive amounts of money on restaurants, shows, and gifts while dating have turned out to be very stingy with their wife after they got married. How much a man spends on a woman while courting her is in no way indicative of how he will treat her after he marries her. Please bear that in mind, even though you think you know a lot about dating in the five years that you have been out there in the shidduch world.

Then there are men who are very active in the dating pool and go out with many women; when they start adding up how much money they have spent in a short amount of time, it sometimes reaches a point that they want to trim down their expenses. They may plan to spend much less money on the first few dates with someone new. There is nothing wrong with initially establishing compatibility with one another before springing for an expensive meal or other activity, especially in the early stages of what may never even turn into a relationship. Another thing to bear in mind is that among the younger crowd, oftentimes the parents are funding their sons on dates, and the truth about a man’s finances often first comes to light when the relationship is advanced.

When I started writing my response to you, I validated your points of concern, because whatever is going on in his life with regard to his divorce and finances has nothing to do with you. You had honorable intentions when you accepted a date with this man. You demonstrated good character that you had no expectations of anything more from that date than the opportunity to get to know one another and determine whether there is any compatibility.

Though I have compassion for what he is going through in life, and I respect that he has the emotional energy to be proactive in rebuilding his life, he should not be placing anyone else in the same awkward situation as he did to you. When a man cannot afford to spend money on two sodas, and I assume he must have spent money on car fare or other means of transportation, he should not date in that manner. It might be in his best interest to take a walk someplace with a woman and bring along bottles of water or other snacks for the date and make it a relatively free fun activity. There are also many other recreational facilities that are free of charge, where spending money is not even a consideration. In fact, I advise singles of all ages to do that, particularly on a first date. You might want to relay that to the shadchan to suggest that to him for the future.

I will address your last question about whether this type of situation occurs in the yeshivish circles. After dating only modern Orthodox men, this is your first experience with a man who is hashkafically more to the right. I assure you that he does not represent the yeshivish hashkafic leanings where it relates to dating. As a side note, I get plenty of calls, e-mails, and texts about awkward dating situations among the modern Orthodox circles.

I had a recent case where a modern Orthodox couple took a walk in a park and the young man suggested that they get ice cream afterward. The young lady accepted the offer. However, the merchant selling ice cream would not accept a credit card, only cash. The young man did not have enough cash in his wallet for two ice creams, so he bought only one—for himself! In other words, he was enjoying the ice cream while the young lady was watching him eat it. When she declined to go out with him again, he was in total shock that she rejected him, since according to his reflection of their date they had so much in common. Bad middos, poor judgment, and impulsive reactions exist in all circles.

What may be more prevalent in yeshivish circles is the educational element. You stated that the man was learning for a few years, and then he went to work for his father-in-law, so he did not have the opportunity to advance academically. I imagine that since he was no longer a member of his ex’s family, they did not want him to be part of what may be a family business. That’s a heartbreaking and unfortunate circumstance that is not uncommon.

The tragedy is that whatever his age may be, he now finds himself financially strapped, and he likely has no clue what to do about it, where to turn for help, and when he will get back on his feet. As a kind human being you can feel badly for him with regard to what he is enduring, but you have no obligation to date him. Keep in mind, though, that what this man is going through can happen to anyone—modern Orthodox, yeshivish, someone with a degree, etc. If a person worked for someone for a long period of time and suddenly finds himself out of a job, that college degree may not help him much either. Or, a woman could marry an employed man and he loses his job, G-d forbid.

I am happy that you are cognizant about the importance of kind understanding and respect in dating situations. Continue to keep an open mind and date men who are of various hashkafic leanings if you find compatibility with them. The most important aspect is how the man you date feels about you and how he treats you as a woman. That should be on your list of top priorities.


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 Baila also hosts The Definitive Rap podcast for, Israel News Talk Radio, WVIP 93.5 FM HD2, and Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at


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