One of my close friends is in a relationship, but I'm pretty sure his girlfriend is cheating on him. Am I obligated to confront her? Should I tell him what I think is going on? I don't think I can just leave this alone.

This is a very hard position to be placed in, and I applaud you on your sensitivity to wanting to do it right. It seems to me that there are two central issues here, at least in terms of your response to the information that has come your way, the issue of remonstrating with a friend who is acting wrongly and the issue of spreading negative news. For the first, the Torah does tell us that when we see something in our friends that is imperfect or improper, we should try to speak to them about it and help them find their way away from that conduct. Here, that would suggest-- it gets more complicated, so this is not the final conclusion--that you should, indeed, speak to the girlfriend, gently and privately at first, and increasingly harshly if she ignores your first overtures.

That approach, however, has been recognized to be often ineffective for thousands of years. The Talmud already notes that there is a limit to how far someone has to go with remonstrating others, although the Talmudic standards would seem to require us to remonstrate with others until at least when they yell at us, or speak harshly back to us. Nowadays, we generally recognize that most people will not take our rebuke/remonstration well, and stay silent. So, in this case, if you know the girlfriend well enough and think she might be receptive to what you have to say, you might try, positively and constructively at first, to engage her in conversation around the issue. She might be feeling guilty already, and this might give her an excuse to unburden herself, and to brainstorm over how to make this better. But if you have no such relationship, it's hard to imagine a confrontation will produce much good.

What you might do, though, if you decide to go to your friend with your suspicions, is warn her about it first. While this will upset her, no doubt, it will also give her a chance to end her cheating relationship and think of how she wants to handle the crisis.

As to the boyfriend himself, your level of obligation depends on the reliability of your information-- if you saw the girlfriend in the act of cheating, you'd have to tell your friend, because that is part of protecting him from further loss (time, energy, and money he'd be putting into this relationship). With anything less than that, though, you'll want to couch your discussion in appropriately cautious terms, being very clear about what you know and leaving to him to decide how to pursue it. So, if you've heard consistent rumors about her, you might say, "Listen, I don't know if there's any truth to these rumors, and there may not be for all I know (since that is all you know), but I think you should be aware that there's this persistent rumor that..." If you have information better than rumor but less than seeing it yourself, say that; it is just important to remember that he is emotionally invested in this, and that your information is only as good as it is.

When you tell him, then, be sensitive to how difficult it might be for him to accept, and therefore be doubly cautious about how certain you are about your conclusions. If you've just seen her with this other guy, laughing and flirting, you can say that, but don't draw any further conclusions-- just tell him you were concerned, you don't know what it means, but you'd hate for him to not know about this and then be hurt later on.

Your goal, throughout, should be to help each of these people get to the best place possible for them, either by approaching her in a way that obviates the need to go to him at all, or by approaching her and then him, but telling him only what you actually know, and suggesting to him that he look into it further. It's a tough situation to be in, and I wish you luck with how you handle it.
Answered by: Rabbi Gidon Rothstein

Thank you for this question and for your impulse to help a friend. There is no easy or immediate solution to this and sometimes our lesson in these kinds of cases is that we are not able to control the world or others. No one of us is God. Once we’ve concluded that we’ve done all we can to help a situation we must accept that certain things are in God’s hands and our interference is unproductive and possibly detrimental.

The first thing, however, is that you must be clear about whether or not cheating is actually happening. Cheating is a heavy accusation and if you make such an allegation without knowing for sure, you may risk losing your friend’s trust. It may be worth the time to ensure you have the truth before doing anything.

If you feel as though you are convinced she is cheating, you may wish to confront her directly. Your question to her should be framed in the values you are upholding, namely your dedication to the well-being of your friend. In other words, this cannot be about you or about her – it’s about your friend, his loyalty to her, and his feelings. Your sincere care for your friend is probably the only way to garner her honesty and trust.

There are three potential outcomes of confronting her: a) you learn that she is indeed cheating; b) you learn that she is actually not cheating; or c) you are still unsure one way or another. In any case, your role is limited to helping to facilitate their open and honest dialogue – again, it is not for you to control their relationship. Therefore, if you learn she is cheating, you should advise her to speak with your friend and tell the truth. What he decides to do then is up to him, not you. If you learn she is not cheating, it might be wise to apologize for doubting her, as she deserves that respect and your renewed confidence as a friend yourself. And if you are still left in doubt as to whether or not she is cheating, you may then have to accept that doubt and trust that the truth will eventually emerge, which it almost always does (that’s the wonderful thing about the truth).

My only question for you is: Why can’t you leave this alone? Here is something that you are not entirely sure of yourself, but you feel absolutely compelled to get involved. I am all for sticking with friends and “watching each other’s backs,” but we must give pause to such sensitive compulsions. Matters of the heart can be volatile and if we choose to step between two hearts it must be done with calm reason, and without prejudgment.

In the end, remember that it is only your actions that you can judge. You are not in the position to rightfully judge either your friend or his girlfriend. Your conscience is the only one that you are ultimately responsible for. And if your conscience is clear, then you know you’ve done the right thing.

Thank you again for this sensitive question.
Answered by: Rabbi Paul Steinberg

Thank you for writing to Jewish Values Online.

This is indeed a delicate issue. People’s feelings and relationships are at stake, and you cannot act without great care and attention to all the factors.

The principles at stake here fall under the general categories of Lashon HaRa (evil tongue - speaking ill of someone), Tochecha (reproof or correction of someone’s faults), and Shemirah (guarding or protecting someone from harm). The concepts are easy; it is the delicate balance that is required to apply them correctly that is so difficult. >
Answered by: Rabbi Joseph Blair