Dear Navidaters,

My younger brother has been dating a girl for two months. Until now, all he told me was her first name; he’s generally a more private person. She ate at our house for Shabbos this past week. I was shocked to notice she is the same girl as I saw while in seminary a few years ago who was friends with the party girls in the seminary I was a madricha at. She did not go to the same seminary I was working at, rather she hung out with the more messed up crowd from my madricha year.

I don’t want to ruin my brother’s shidduch, but I feel like I need to tell him. I just feel so guilty doing it.

What is the best way to break it to him?

The Rebbetzin

Rebbetzin Faigie Horowitz, M.S.

Be strategic and smart. Tell him you recognized her and from where. Make it a chatty conversation and let him lead with questions.

Talk him about your madricha experience and what trends you noticed. You may carefully say something about seminary being part of a transition for some girls. The year in Israel for many is a learning process of making choices and owning a lifestyle, hashkofos, and perspectives. Talk about all these topics, spoken and unspoken, that concern seminary teachers and mechanchos. This is your opportunity to give context and perspective to the girls fresh off the plane that he may be dating.

Without knowing more about your relationship with your brother and wheth- er he trusts your judgment, it’s hard to make more suggestions other than to say go about this indirectly at first and see where it leads.

The Shadchan

Michelle Mond

Let’s break down your question.

Your younger brother is dating a young woman who used to hang out with the party girls at the seminary you worked at a few years ago. You do not know she was partying, and you do not know her relationships with these girls. You do realize this was from years ago. For all you know, they could be related or even neighbors back at home. Yet, you would risk your brother’s shidduch because you feel compelled to say some piece of superfluous information that you know. If you saw her often at the doctor’s office, would you then relay that it could be she has a terminal illness she may be hiding?

This is an unfortunate flaw to the shidduch system. While we simply cannot exist in a bubble, many outsiders see us every day and impart their own thoughts and opinions about us. Then, inevitably, it filters into shidduchim and can lead to rumors and lashon hara.

You don’t ask if you should tell him but how. May I ask you a question? What compels you to feel like you must “break it” to him and what, exactly, is the terrible news you would like to break to him? Do you have any faith in him to build an honest and open relationship with her on his own?

My advice is to simply stay out of it and trust his judgment. You don’t need to say everything you think.

The Single

Tzipora Grodko

Firstly, it’s extremely unfair that you’re assuming you know this girl based on who she hung out with back during the seminary days. You have no idea what she was struggling with, experiencing, or who she evolved into during that timeframe.

I know you mean well, but this is the epitome of gossip (and frankly, the ridiculous notion that one chapter of a dater’s life is defined by their one challenging or transformative year of development).

Spend time getting to know this girl, trust your brother’s judgment, and try to let go of your biased reason recognizing that it’s super limited. I didn’t hear you discuss any red flags nor display any current behavioral concerns. Focus forward, not back.

The Zaidy

Dr. Jeffrey Galler

To tell or not to tell, that is the question.

Is it a huge mitzvah or is it a huge mistake to tell your brother what you remem- ber about his girlfriend?

Different iterations of this dilemma have appeared in the Navidater column over the past several years. There are different levels of possibilities to consider.

First, the behaviors that you describe happened some time ago. People do grow up, mature, and change. Perhaps she is now a much better person than she had been when you knew her. It’s probably best to say nothing and trust your brother’s good judgement.

Second, if you do, nevertheless, feel strongly compelled to get involved, call her up, tell her that you enjoyed your Shabbos meal together, and invite her to meet for a coffee. There, you can quietly assess if she is still the same, troubled person.

Third, if, after all that, you still feel strongly that the girlfriend is very “messed up,” you may wish to consider what Rabbi Avigdor Miller, zt”l, often advised. You can send an anonymous letter to your brother, advising him to carefully check his girlfriend’s references.

Now, readers of this column might find the following interesting:

You have probably heard that various companies have developed Artificial Intelligence (AI) computer programs that give human-like responses to questions. I signed up with a program called ChatGPT and asked it to respond to this week’s Navidater question.

I was astounded by its response. In less than a second, it texted, “It may be best to keep your opinions to yourself. People can change and grow, and it’s not fair to judge someone based solely on their past behavior. Your brother may also be aware of his girlfriend’s past and may have already made his decision about whether or not he wants to continue the relationship. Ultimately, the decision of whether or not to tell your brother is up to you, but it’s important to approach the situation with empathy and understanding.”

Wow! Now, I can’t stop wondering if this plunge into Artificial Intelligence is enlightening or frightening?