DATING FORUM

By: Baila Sebrow

Question

When my friend became single and started dating again, she usually turned to me for advice. She was unfamiliar with the dating world, and whenever she began dating someone she would ask me if I knew the person and what I might know of him. I was always honest with her, and she appreciated my guidance.

Recently she told me she was dating someone but was secretive about his identity; she didn’t tell me his name. Then, out of nowhere, she announced that she was engaged and finally revealed the name of her chassan.

The problem is that I know certain things about him that I believe would be important for her to know before marrying him. Right before the vort, she asked me whether I knew him. But by then, they were already engaged, and I felt it was too late to say anything, so I pretended that I didn’t know him.

Now I’m struggling with what to do. I don’t understand why she was so secretive about the relationship, especially when she always trusted me to seek my advice in the past. I don’t want to farshter her shidduch or make problems for her. At the same time, if what I know could affect her future, I would feel terrible if I remained silent and something went wrong. Should I tell her what I know, even though she is already engaged, or should I keep quiet?

Response

You are in a difficult position, and I understand why you’re struggling with this decision. You care about your friend, you have a history of being someone she turned to for guidance, and you’re now holding information that may or may not be important to her future.

But before deciding whether to speak up, I want you to consider a fundamental question. If you truly believe this information could materially affect your friend’s decision to marry this man, would remaining silent truly be the kindest thing to do? The answer depends on what you know, how reliable that information is, how relevant it is to the marriage, and whether sharing it would genuinely help your friend make an informed decision. There is no universal answer that applies to every situation, but there are principles that can help you navigate this dilemma responsibly.

First, let’s address the fact that your friend is already engaged. An engagement is a joyful milestone, and no one wants to be the person who introduces doubt or distress into what should be a happy time. You may fear being blamed for disrupting the engagement, losing the friendship, or being accused of trying to sabotage the shidduch. Those concerns are understandable. But an engagement is not a marriage, and the fact that a couple has announced their intention to marry does not automatically make every difficult conversation off-limits.

If you know something serious and credible about the chosson that could affect your friend’s safety, well-being, or ability to make an informed decision about marriage, the fact that she is engaged does not erase the importance of that information. In fact, the closer a couple gets to marriage, the more painful it can become to discover that someone knew something significant and chose not to speak.

Imagine learning after the wedding that a friend had possessed reliable information about a serious issue involving your spouse before the marriage took place. Would you be comforted by the explanation that your friend didn’t want to ruin your vort? Or would you wonder why someone who cared about you allowed you to proceed without giving you the opportunity to consider something that might have changed your decision?

Of course, not every negative comment, past mistake, or unflattering story warrants intervention. People are complicated, some people have a history, and no one should be judged based solely on gossip, rumors, or another person’s interpretation of events. But there’s a significant difference between sharing irrelevant information (that could cause unnecessary pain) and responsibly communicating something that a person genuinely needs to know before making a life-altering decision. That said, the question is not whether the information might upset her. The question is whether it is important, reliable, and appropriate for her to know.

Before taking any action, I would urge you to examine the information carefully. Is it something you personally witnessed? Did someone tell you something directly? Is it based on reliable information, or is it something you heard through the grapevine? Is it current, or does it concern something that happened many years ago? Has the person changed? Is there context you may not know of? Most importantly, is the information genuinely relevant to his suitability as a husband, or is it simply something unflattering about his past?

There’s a difference between knowing someone behaved badly in a relationship years ago and knowing he has a pattern of dishonesty, abusive behavior, or any issue that can affect a future spouse. There’s also a difference between a verified fact and a suspicion.

You must be honest with yourself about these distinctions. The purpose of speaking up should never be to punish someone, expose embarrassing details, or prove you knew something first. It should be to help your friend make a decision with information that may be important to her future. If the information is uncertain, you should not present it as established fact. If it is private, irrelevant, or based on speculation, sharing it could cause needless harm. But if the information is credible, dismissing it simply because the couple is already engaged may not be the responsible choice.

You mentioned that your friend had always come to you for dating advice, yet this time she withheld the man’s identity until after the engagement. Naturally, you’re wondering why. Maybe she was afraid that you would have an opinion about him. Perhaps she wanted to protect the relationship from outside influences while she was still getting to know him. Maybe she was concerned about privacy, or perhaps someone advised her not to share the details of the shidduch until it became more serious. It’s also possible that she knew you might have information about him and preferred not to hear it. But at this point, you simply do not know.

Even if she deliberately avoided telling you his name, that does not automatically absolve you of responsibility if you possess important, credible information. On the other hand, her previous willingness to seek your advice does not mean she was obligated to consult you about every relationship. Friendship does not confer ownership over another person’s dating decisions.

You also mentioned that when she finally revealed his name, she asked whether you knew him, and you pretended you did not. I understand why you might have frozen in that moment. You were caught off guard, the engagement had already taken place, and you felt that there was no appropriate way to respond. But now that you’ve had time to think, I would not recommend building your next decision around maintaining that initial response.

You do not need to make a dramatic confession or create a confrontation. But if you decide that the information is important enough to share, you should be prepared to acknowledge that you were taken by surprise and did not know how to respond at the time. Stress that you don’t want to hurt her, interfere in her happiness, or make decisions for her, but that you would feel uncomfortable keeping something significant from her. Ask her if she would be willing to have a private conversation with you about it.

That approach gives your friend the opportunity to hear you without immediately feeling attacked. If you are concerned that the information is particularly serious or time-sensitive, you may need to be more direct. You should not, however, begin by unloading every detail or presenting your conclusions as the only possible interpretation of the facts. Your goal is to open a responsible conversation, not to dictate the outcome.

From a Torah perspective, this situation presents an additional challenge. We are taught to be extremely careful with our speech. Lashon ha’ra is forbidden simply because it may be true, and the fact that someone is engaged does not give others permission to discuss his shortcomings indiscriminately. At the same time, the Torah does not require a person to ignore a genuine concern when sharing such information can prevent harm.

The halachic concept of l’toeles, speech for a legitimate, constructive purpose is particularly relevant here. The laws governing such speech are nuanced, and a well-intentioned motive alone does not automatically make every disclosure permissible. The Chofetz Chaim discusses situations in which information may be shared to prevent harm, while emphasizing important conditions and limitations. Among the considerations are the reliability of the information, the speaker’s intention, the necessity of sharing it, the avoidance of exaggeration, and the importance of not causing more harm than is justified.

In a shidduch situation, that means a person should neither spread damaging information carelessly nor use the prohibition against lashon ha’ra as a blanket excuse to withhold information that may be pertinent. If you know something that could genuinely affect your friend’s decision to marry this man, you should consider seeking guidance from a rav who understands the laws of lashon ha’ra and the practical realities of shidduchim. Explain the facts privately and objectively, without embellishment or speculation. A rav can help you determine whether the information should be conveyed, to whom it may be conveyed, and how to do so in a way that is halachically appropriate. The goal is not to find a loophole that allows you to say whatever you want. Nor is it to remain silent simply because speaking is uncomfortable. The goal is to do what is right.

There is another important point to consider. You may feel that because your friend previously relied on you for advice, you have a responsibility to ensure that she makes the right decision. But you cannot make that decision for her. Your responsibility, if the information warrants disclosure, is to provide her with the opportunity to consider it. Her responsibility is to decide what to do with the information. She may ask questions. She may want to verify what you tell her. She may explain that she already knows about the issue. She may have information or context that you do not possess. Or she may become upset with you. You must be prepared for that possibility.

Sometimes people become angry with the person who brings them unwelcome information, even when that person is acting out of genuine concern. The information may threaten the future they envisioned, and the person delivering it becomes an easy target for their distress. If that happens, it does not necessarily mean you were wrong to speak. But neither does her anger automatically prove that you were right.

Your actions must be judged by the facts, your intentions, the careful way you communicated it, and whether you acted responsibly, not simply by how she reacts. You should not pressure her to break the engagement, demand that she accept your version of events, or insist that she explain her decision to you. You can be a friend without becoming the decision-maker.

I must also warn you that you may lose your friendship. She may accuse you of jealousy, interference, or attempting to ruin her happiness. She may believe that you should have spoken before the vort, or she may resent you for speaking afterward. There is no guarantee that doing the right thing will produce the desired outcome.

But consider the alternative. If the information is truly serious, credible, and relevant, and you remain silent solely because you fear her reaction, will you be comfortable with that decision later? At the same time, you must resist the temptation to justify speaking simply because you would feel guilty if you did not. Guilt alone is not proof that disclosure is warranted. Sometimes we feel responsible for things that are not ours to control. This is why the nature of the information matters so much. If it concerns a serious issue that could affect her future marriage, and you can communicate it responsibly, I would lean toward finding an appropriate way to make her aware of it. If it is an unflattering story, an old grievance, an unverified allegation, or something that has no meaningful bearing on her future, I would be much more cautious. There is no virtue in creating pain for the sake of saying something. There is also no virtue in withholding important information merely to preserve your own comfort.

Here is a very strong and stern warning. Do not discuss the matter with mutual friends, post about it, or turn it into a community conversation. And one more thing, do not let your hurt over her secrecy become part of the motivation for your decision. Whether she intentionally withheld his name or simply wanted privacy, that is not the issue you need to resolve right now. The issue is whether she should know something important before entering a marriage. 

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 [email protected].