Thanks for the question! I'll quote the original question from the thread here:
On shabbos I was having a conversation with a relative of mine who is going on a fifth date tom. He is having a hard time "taking the conversation to the next level", in other words, moving from chit chat kind of talk to more serious talk. He is definitely a deep thinker and does appreciate intellectual conversations but isnt the touchy feely type and doesnt just open up that easily (like most guys). Does anyone have any good ideas of questions or things to say that would start a deeper conversation or that would lead to a more "opening up" kind of talk?
To start with, when this boy talks about taking the conversation to the next level, is he looking to have a deeper conversation intellectually or emotionally? He's described as
a deep thinker and does appreciate intellectual conversations but isnt the touchy feely type and doesnt just open up that easily
so not clear. But in order to make this practical for everyone, we'll deal with both independently.
Deeper intellectual conversation:
Think of what kind of topics you would like to be talking to your spouse about. What thought topics do you enjoy discussing with your friends? Hashkafa? Themes in literature? (That's wasn't meant as a joke, just in case someone suspects it is - every person is going to enjoy a different kind of conversation, so identify what you like.)
Then come up with a question on it. If it's a topic you enjoy, you probably have one - either unanswered, or a question you have an opinion on already, but would like to hear your date's opinion.
You can broach the question by starting, "You know, there was a conversation I was involved in recently, and I wanted to get your opinion on the topic..." or something of that sort.
And if you really want deep, don't just stop at his/her initial answer. Probe deeper. Keep asking questions (not as interrogater or someone giving a ferher, but as a conversation partner who is really interested in the other party's opinion).
A few of the answers in the original thread dealt with this angle. If you've been chitchatting for a few dates already, your date has probably mentioned something that hints to an underlying emotion. Bring it up. Say, "I was thinking about what you said last time about when your chevrusa decided to leave yeshiva. How was that for you?" Follow up questions could include, "How did you deal with it?" "Does it still bother you?" Make sure to empathize with him ("Sounds like that must have been really rough") and not just direct questions at him.
The idea of mentioning an incident that evoked emotion in you, sharing that with him, and then seeing if he has feedback or a reaction to it (i.e. "did you ever experience something that made you feel so excited/depressed/petrified") is another idea.
The ability to share both positive and negative emotions with your spouse is critical to a happy, healthy marriage. One really good book on it is Dr. Meir Wikler's "Ten Minutes a Day to a Better Marriage." I know a couple who started using the approach while dating and found it very helpful to the development of the relationship (and seeing where there were issues in the potential relationship that would need to be worked on).