- Ask the person if they have experienced heartbreak.
This tells you a lot about the person’s character. If she answers in the negative, it’s possible the person has emotional intimacy issues. If the answer is yes, it demonstrates humility. This leads to the next question.
- When was their last relationship?
You want to know if she is coming to you with a clean slate. Some people bring in old relationships with them, adding strain to the relationship. One must be fully ready to take on a new relationship and it is essential to know if they left the last one behind.
- How long was your longest relationship and why did it end?
If she doesn’t own up her half of the reason for ending the relationship, you don’t want to get involved with her. It takes two strong individuals to establish a relationship that is both healthy and loving. It also takes two people to ruin a relationship through lack of communication and trust.
When your conversation takes on a serious and heavy tone, ease up the atmosphere by gradually reverting to the easier or simpler questions. Make sure that the “easing the tension” questions are still related to the topic at hand so the mood will not become awkward or that you don’t emphasize the fact that it’s become really in-depth.
Be careful not to zoom right into sensitive territory too fast. Your eagerness to know your date more may propel you into that zone before she’s comfortable to do so. She may end up being defensive – and you may not get the answers you need. Think of the whole getting-to-know-you process as one that is like peeling away layers of onion skin or flower petals. You’re watching her unfold herself gradually, at a pace slow enough for you to take time to digest what she said and appreciate her fully.
Always remember that you will also have to answer your own questions. So be prepared to do so when you ask her the more serious ones.