How to ask about difficult topics on a date

Sharing/ Disclosing about your ‘stuff’

There may be something that you may have heard about the person you are dating and they may not (yet) have brought it up. If you have a question you should bring it up.

For starters, the information may be important to know.  There may be things that you are not comfortable with (and that’s OK).

Also important is the way you can talk about uncomfortable and vulnerable topics. In married life, there will be many uncomfortable topics that you will have to discuss. This is an opportunity to experience how you two can have such conversations.  Do not defer this conversation to a shadchan or research to find out the information; you will be missing an important opportunity.

How to ask

Mindset

  • You want to build your marriage on solid trust and open communication, even if it is uncomfortable.
  • You want to know who the other person is – warts and all.
  • You will survive if the other person is not who you wish they are.

Anticipate that they will be uncomfortable

  •  This part of their life might be uncomfortable for them to talk about. They may also feel that it is private and that they should control how and when to share.
  • Allow them to share in bits rather than all at once.
  • They know what is important for you to know. Don’t pry. That said, if there is something that you need to know a specific detail, explain why it is important to you.
  • As best as possible, create an environment of trust.

Wording you might use

Entry point. Ask permission. That prepares them for an uncomfortable conversation that may follow.

  • “There’s something on my mind. Can I bring it up now?”

Introduction. Provide emotional safety. Allow the other person the space to say that they are not yet ready to talk about it.  Allow them to control the flow of the information.

  • “I heard some things about your family. I want to understand it better. Can we talk about that now?”
  • “I know you had some challenges in your later teenage years. I want to understand that more. Can we talk about that now/ next time?”
  • “How would you like to have this conversation?”

Ask. Ask your question in nonjudgmental words. You might describe what you already know and ask them to tell you about the accuracy and their side of the story.

Extroduction. At the end of their sharing, thank them and assure them 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.”

Related

Dating at the Speed of Trust

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