Rabbi Raffi Bilek
The 36 Shailas That Lead to Love
So the 36 Questions That Lead to Love comprise a list of questions that become increasingly intimate (by which I do not mean graphic or inappropriate). They were created as a part of an experiment to see if love can be invented instead of discovered, the idea being that the more you let someone into your self, the more connected you will feel. For those of who you are unsure what to do on an actual shidduch date or what to talk about, this list is a handy reference.
Obviously, you should start at the top of the list and work your way down – slowly. One does not on the first date open up question #29 (“Share with your partner an embarrassing moment in your life”). But it might very well be something appropriate a few weeks into things. It does take some judgment.
Fortunately, the start questions are really great for learning about each other in a very non-threatening way. “Given the choice of anyone in the world, whom would you want as a dinner guest?” is a great conversation starter! (If this exercise yields one-word answers and no more – “Rambam.” “Oh.” – then one or both of you are doing something wrong.)
I found the list very intriguing and can imagine many hours of discussion arising from these. Maybe you will as well.