Our first impulse might be to pick up some current event or to talk about how good or bad the food is or mention a few impressive things about ourselves. But if a date is the test of the heart then we must talk about things that help two people understand each other at a deeper level.
We shall know that the heart is succeeding at the test if at some point during the date, the person on the other side of the table tells us that he/she has never been asked such heavy, psychologically-weighty questions. This only goes on to tell how surficial most conversations are, how less they reveal of our souls.
Here are some questions that might help you get a better insightful peek of the other person:
1. What has made you cry recently?
We are not only accepting of their smiles but also of the baggage their heart has carried over the years. We wish to give them the full freedom to not only laugh but also cry in front of us. And in turn, we are also comfortable to shed a tear or two in their embrace.
2. To whom would you like to go back and apologise?
This question might serve as a release for the guilt the person has lived with for quite some time and can even serve as a medium for atonement.
3. What have your exes not understood about you?
This shows our willingness to learn from where the person on the other side of the table is coming from. We do not want to learn about their exes in order to feel insecure or to point fingers later on. But because we understand that the nature of someone’s past relationships is likely to predict that of their future ones. Also, their depiction of their exes is likely to show whether they have learned something from the past or are continuing to blame or lament.
4. What was difficult in your childhood?
We’re signalling that understanding their younger self will be vital to grasping how they behave and who they are as adults. It will also allow us to be more compassionate when their adult selves are overwhelmed by the dynamics of the past.
5. What do you regret?
We all have had roads that we haven’t taken, choices we did not make or situations we often think about before sleeping. By encouraging others to talk about them, we shall be gifting them what probably no one ever has – a chance to let their mistakes be heard and acknowledged, a chance for them to forgive themselves and realise that such mistakes are a part and parcel of being human.
Some other questions that can be asked are:
6. What do you worry about in the middle of the night?
7. Which of your friends do you envy the most?
8. What would you like to improve about yourself?
9. What is the role of money in your life?
10. What are you looking for in a relationship?