The purpose of a date is to get to know someone in a fun way but it can be too easy to spend the evening chatting and never find out anything significant or telling. Here are 15 questions that can help you learn more about your date's character and values and how well they blend with your own:
1. "What kind of relationship do you have with your most recent ex?"
History is the best predictor of the future. Attitudes your date has towards past beaus can be a clue to where you may stand if things do not work out. If they feel "wronged" by, say, the last five people they've dated, you're not going to be magically exalted from blame.
2. "Why did your last relationship go south? Who ended things?"
This is a lot to ask early on but can still provide relevant information. Listen carefully to the tone in which they share why things ended. You want to see that they are magnanimous towards exes and not full of animosity. Ideally, they accept some responsibility for their role (unless a relationship was abusive, it
always takes two to tango). If their ex ended the relationship, be alert for the possibility that your date may not be completely over it. That's not necessarily a deal breaker but a sign to be cautious and pay attention to signals.
3. "What do friends say are your best and worst qualities?"
Third party views can be very informative. You can also ask:
"Do you have any vices?"
"Do you have any history of addiction?"
"What are your worst health or living habits?"
4. "Do you think partners should share everything or should some things be kept private?"
Gauge your compatibility level with sharing (although comfort levels morph as people spend time together and gain more trust).
5. "What have you learned from your past relationships?"
We all learn from our experiences; it can be illuminating to hear perspective.
6. "Do you feel you are more the caretaker in your relationships?
This can reveal past patterns or the nature of your mate. Do they have a "rescue" complex (or hold the opposite, a sense of entitlement)? Do they feel things were one-sided (and was it accurate)? If there was an unhappy dynamic, what was going on that sustained it? These can be clues to emotional health.
7. "Do you feel comfortable expressing your feelings?"
If you're very expressive, you may want someone similar; likewise if you are more private.
8. "Are you usually on time or late?"
This question can reveal your date's level of conscientiousness and planning, and whether it's compatible with yours.
9. "How do you treat yourself when you want to do something special just for yourself?"
This is a fun way to find out if you have similar styles.
10. "Do you feel people are essentially good or bad?"
Find out if their glass is half-full or empty (and whether or not it matches yours).
11. "Have you ever been fired? Quit? What happened?"
Learn about responsibility, job history and sense of accountability.
12. "What are you most proud of?"
"What risks have you taken? Are there any risks you've avoided"
13. "How do you act under duress?"
How people act under stress is extremely eye-opening. You want someone who is kind and respectful even when things are not going their way. (Keep an eye out for people who say they are one way but then you witness something different.)
14. "What have you learned about yourself emotionally in the past few
years? How have you changed? How would you like to change in the next 5
years? Are there any parts of
yourself that you would like to dwindle or grow?"
This is an enormous conversation topic but very revealing! Learning important information about values early on can help you be selective about where to invest your time and energy. It generally seems to take about 3-5 months before people relax around each other enough to show true character so enjoy your date(s) and let time unfold.
