Dating can pose a multitude of delicate and sensitive questions that require the assistance of those who spend countless hours dealing with singles. In each installment of the Five Towns Jewish Times Dating Forum, a question pertaining to contemporary dating issues will be addressed by our diverse and experienced forum panelists. Questions and comments can be submitted to 5townsforum@gmail.com.
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Question: My son has been dating for several months. Often, after the first date, he claims he knows with certainty that the girl is not for him. He is conflicted about how to proceed: He is convinced the relationship won’t develop and therefore further dating is a waste of time and money, and will likely give the girl a misleading impression. On the other hand, he fears his reputation will be damaged if he doesn’t give a courtesy second date. Is a courtesy “chesed” second date always expected and necessary? Should he fear that he’s doing something wrong by ending it after one date?
The Panelists Respond
Bashi Salzman:
This is a very good question and one that I think about often while setting people up.
Shidduchim are not usually about statistics. Although the majority of couples have no idea if their dating experience will end up in a marriage, on a first date one or both parties are very nervous and are not able to show their full depth and personality. Even if in some cases the boy and girl are comfortable, there are many layers to a person and it takes time for a real relationship to develop. You are not doing a chesed by going out on another date; rather, it is the right thing to do and you are only helping yourself.
There are definitely boys who get a reputation that they dump after one date, and this is certainly not a path you want to take. Going out on a second date is the mature way to approach dating, and giving a girl the time to open up and show who she really is can be your “chesed.”
Bashi Salzman is a Far Rockaway shadchanis. She can be reached at cbs729@aol.com.

Madeline Gross:
This prevalent dilemma is difficult to answer decisively. The appropriate course of action is subject to the reasons provided and the introspective ability of the given dater. Some reasons are more cogent and some daters have a better ability to attain clarity of mind. But I will try to outline some important points to consider.
Shadchanim will often push reluctant daters to give it another shot. The rationale behind this prodding is that certain compatibilities are often missed in the highly tense and nervous atmosphere of the first meeting. It is common for a dater to feel they are not acting like their usual self with the pressure to make a great first impression. Tongues get tied, thoughts become scrambled, the “life of the party” becomes lifeless, and the intelligent resort back to their 3rd-grade vocabularies. Time allows for added comfort and the ability to objectively see the entire person’s character traits in normal form. This applies to physical attraction as well as religious and more ethereal allures.
However, this is not to say two dates is an absolute requirement. There is certainly a valid argument not to agree to a date when your son is absolutely convinced it will not go anywhere. I simply caution that you make sure your son can properly articulate why giving it another shot is useless. It is difficult to believe that, if your son has set realistic standards, portrays himself honestly, and enters each date with the attitude that he wants it to work out, he can consistently be certain after merely one date that it will not work. In these cases, the mindset and attitude when entering the date is often the culprit.
Even in the event that your son is completely convinced, another factor that can play a role in this decision is how your son feels the girl enjoyed the date. Very often, daters can get the impression that the feelings about not continuing are mutual. If the girl’s feelings weren’t evident, the shadchan can be a very useful tool when it comes to gauging how a first-date “no” will be received by the girl. In a case where your son or the shadchan doesn’t feel it was mutually understood, a “chesed” second date should be considered to avoid wounding someone’s self-esteem.
Although this question is from the boy’s perspective, the same basic advice holds true for the girls as well. I am an advocate of erring on the side of caution if there is any degree of uncertainty. Daters should consider doing themselves a chesed by swallowing their pride once in a while. Don’t worry, it’s not fattening.
Madeline Gross is a Woodmere shadchanis. She can be reached at madelinegross1@gmail.com.

Matty Sod:
Good question! When they first start dating, both boys and girls are advised by their mentors to always agree to a second date. After all, they are told, one never knows. Just a few years ago, most daters were heeding this advice. But, nowadays, we’re in “shidduch crisis” mode. Boys are being inundated with names, while girls sit around waiting for just one decent suggestion. Ask almost any good boy in shidduchim, and he will tell you that he could date every single night, if he so desired. Many boys (and girls, too) are getting “burned out” from dating, especially if they feel they are being pushed into going on second dates that are not shayach for them.
So, these days, unless they feel there is some potential, many boys are not agreeing to a second date. The most common reason they give is that they don’t feel any “chemistry,” i.e., attraction. They very rarely change their minds about this issue, even after a second date. I do feel that if everything else is great, attraction can grow. But most boys are not willing to wait and see if things will develop. After all, they have so many girls on their “lists.”
I always advise boys to go on a second date, if they have some interest in the girl or if they are really not sure. Sometimes, though, one knows for sure that the shidduch is not right for them—for example, if there are major hashkafic differences or major differences in life goals. In that sort of case, it is usually pointless to go out again, and may actually give the other person false hope. Especially when neither side is excited about the prospect of a second date, why bother with it?
You say that your son “often” does not go out again after a first date. This seems to indicate that sometimes he does go out with a girl more than once. I don’t think your son needs to worry about his reputation, just because he does not go on a second date with every girl. Plenty of guys don’t give every girl a second date, and they’re still being redt shidduchim.
May your son find his bashert very soon!
Matty Sod has been an active shadchanis for over 15 years. In addition to making shidduchim, she mentors singles throughout the dating process. She has written many articles on shidduchim and can be reached at mattysod@verizon.net.
Suri Flegman:
This is a question that is often asked. Although I do agree that sometimes you just have a gut feeling that the shidduch will not work, for the most part giving a second date is a wise and correct decision. Many people are not really themselves on a first date and should be given the opportunity of a second chance. I feel that unless the first date is an absolute disaster, a second is called for.
Additionally, I certainly am not worried about giving a misleading impression. A second date is at such an early stage that it represents no affinity or commitment at all. This is not a valid concern.
I also think that saying no to someone after only one date can be construed as a real insult. Even if you feel there is no potential, giving a second date makes the other person feel at least like they’ve been given a legitimate chance. No harm ever comes from being a mensch. And maybe you will see things differently on date number 2. It’s certainly happened before! I have seen couples that literally continued for the first few dates only with major arm-twisting (one of the parties clearly would have said no after date 1 or 2), and are now very happily married.
“You never know” are three words that drive singles crazy, but definitely hold real value in my book. I’m a believer!
Suri Flegman, a Lawrence shadchanis, can be reached at papimami86@aol.com.

Rabbi Yair Hoffman:
The “second date” issue is not a simple one. There are stories of many gedolim who did not wish to hurt the girl that they were dating and thus continued. At times it is an embarrassment to the girl when the boy does not wish to proceed after just one date—particularly if it is a girl who does not date much. It can be a blow to her self-esteem, something that by all means we wish to avoid.
On the other hand, the time and money factors are issues that should also be taken into consideration. The rule of thumb should be that if the young lady would not be particularly hurt if your son explains that she is a wonderful girl but he just doesn’t see it, then he should stop after one date. If there is a chance, however, that a rejection may strike at her self-esteem, then it would be a proper thing to go out on a second date.
Rav Chaim Shmulevitz writes that Peninah was punished even though she did nothing wrong to Chanah. The very fact that Chanah was hurt on account of Peninah’s actions, even though Peninah meant and did no wrong at all, was cause for Peninah to be punished. Rav Chaim Shmulevitz explains it as if it is a law of nature.
In order to mitigate the cost in terms of both money and time, I’d like to make the following suggestion. Your son should use the time on the date to think of someone else for her, such as one of his friends. In this way, he will be fulfilling the very important mitzvah d’Oraisah of V’ahavta l’reiacha kamocha. His time and money will be spent on the involvement in a mitzvah, and he will be engaging in gemilus chasadim, one of the three activities that maintain the world (see Pirkei Avos 1:2). It should, of course, never be revealed that his dating is for gemilus chasadim purposes, and the mitzvah of uplifting the esteem and self-perception of a bas Yisrael should be done with the greatest kavanah. It could very well be that in the merit of his being concerned for the future shidduch prospect of the young lady he has just dated, Hashem will bring him his proper zivug even more quickly.
Rabbi Yair Hoffman, a 5TJT contributing editor, is a mechanech, author, lecturer, and rabbi. He can be reached at yairhoffman2@gmail.com.

Baila Sebrow:
It was the perfect evening. The skies were clear, stars twinkling with exuberant brilliance. Yossi had a good feeling about this upcoming shidduch date. The shadchanis promised his mother that the girl is beautiful, comes from a fine family, and attended the best schools and seminaries, not to mention that her siblings attended only prime yeshivas and the mechutanim are pillars in their communities. Yossi shows up at the girl’s house, and in his mind concurred with the shadchanis’s opinion that, yes, this girl is perfect.
The date was everything Yossi could have imagined it to be. The girl was indeed beautiful, had impeccable midos, said the right words at the right time, smiled when appropriate, and nodded when needed. When Yossi returned home from his date, he told his parents that he had found his bashert. His parents were overjoyed hearing this wonderful declaration from Yossi. They immediately called the shadchanis and informed her that a second date is to be scheduled as soon as possible. No sense waiting too long, was their perspective.
To everyone’s disappointment, the second date deviated to disaster. What could have caused such a negative metamorphosis? Yossi went out on a second date and noticed that which was not apparent on the surface. Everything that emanated as positive qualities on the first date was the complete opposite the second time around.
This scenario commonly plays itself out in many circumstances, especially for one who is new on the dating scene.
In response to your dilemma and query, your son has been dating for several months. According to what you are stating, your son feels confident in his perception that after the first date he knows with certainty whether the girl should be granted a second date. In fact, he considers a second date as a courtesy “chesed” to the girl if his heart is not completely into it.
Dating is a decision-making process which can result in long-term, life-altering ramifications. The only chesed your son is showing is to himself. If he takes a girl out on a second date begrudgingly, it will be conveyed in his mannerisms, regardless of advanced etiquette skills.
The only fear your son should be feeling is whether he is doing something wrong to himself by ending it after one date. As in the portrayal of the above scenario, first dates can be deceiving. At times, a first date can feel as though two halves of souls were finally established as one, and contrastingly can also feel like mismatched shoes. The benefit of a second date is to give both parties the opportunity to review what may have initially manifested as either awkward or spectacular.
Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis. She can be reached at Bsebrow@aol.com.