Q: “I am dating Leah and she seems like a great girl. I heard some rumors about her family though she hasn’t said anything. Should I just assume that what I heard is just gossip from angry neighbors? I do want to get to the bottom of it. If I ask outright, Leah will be hurt and I don’t want to mess this up. Please help me figure this out. Thanks, Chaim.”

At Adai Ad, we get such questions all the time.  Yes, some topics are harder to bring up while dating. Some details of your life are uncomfortable to share. We bring our whole selves into the marriage and it is important to really know what you are getting into. And that you know that the other person has a full picture of what they are getting into.

The goal of shiduch dating is to find out if you will be good partners in life.  Does the other person want what you have to offer?  Do you want what they have to offer?  Will you be comfortable in their life? Will they be comfortable in yours?  Do you have similar values?  Can you accept the whole of who they are? Do they know and accept the whole of you?

It is critical that you share the aspects of your life that will impact whoever joins your life.  You shouldn’t withhold that information.  The surprise and betrayal that they will experience when they find out can quickly implode the relationship.  More importantly, you want to know that they accept all of you, especially  that aspect of your life that you are nervous to share (for example: debts, medical conditions, family situations, and mistakes that still impact your life). 

The question is not if you should share, but rather how and when to share.

It’s your story, your issue, your life. You should plan how to share it.  You may share a little and see the response and then share some more.  Depending on the topic, you may bring in materials or a professional to better explain the situation and the implications. You should also prepare your statement for not sharing more than you feel comfortable or is necessary.

During dating, it is crucial that you both know that you both understand and accept each other.

To that end, you should summarize what you heard to make sure that you understand it fully. Make sure you are very aware of how it will impact your life.  Ask questions.   “So, what I understand about this is …. Did I get that right?  Is there something else that I should know about this?”

Similarly, you should ask your date to summarize to you what they understood; you want to make sure that they get the whole picture and are OK with it. “I want to make sure that I explained this fully. Please tell me what you understand so I can clarify anything.” “Please ask all questions that you may have about this. It is important to me to know that you understand it all.”

Sometimes, the other person is uncomfortable sharing something about their life.  It is your responsibility to help them share so that both of you know that you accept each other.  You can start the conversation with, “I know this is your story and I would never share it” or “What would make you more comfortable to talk about it? Perhaps if we walked side by side rather than sitting down face to face? Maybe in the car?”  “This is your story and you know what is important for me to know. If I ask a question that isn’t necessary for me to know, just tell me.” “If you’d like, you can tell me just a little this time and we can pick it up again later.”

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With that in mind, this is what I ended up writing to Chaim in response to his question:

If it is on your mind, then you should bring it up.

Start with asking permission to go to a personal topic. “There’s something on my mind. Can I bring it up now?”  That prepares her for an uncomfortable conversation that may follow.

“I heard some things about your family. I want to understand it better. Can we talk about that now?” That provides her with a space to say that she is not yet ready to talk about it. It also sets the tone that she can control the flow of information.

“How would you like to have this conversation?”  Again, this gives her the control. 

And then just ask. In nonjudgmental words. You might describe what you heard and ask her to tell you about the accuracy and their side of the story.

At the end of her sharing, you can thank her and assure her that you would never share anything.  Not even with your parents or friends as you try to work it out. (In this case, you really should speak to someone who will keep confidentiality.)  “I know that was hard. Thank you for sharing. I have a better understanding of it all.”