Brave dating is dating to discover who you are. A coffee date is a date at a safe location to meet with dates to discover who you are. You don’t have to risk too much to have coffee with someone interesting. Yet this coffee date can do much to reveal to you who you are—to you and your team.

To help this learning process, I’ve got some questions for you to ask yourself and your team.

Ask these questions before the date:

1. What appealing qualities does this person have?
2. What unappealing qualities does this person have?
3. What spiritual qualities does this person have? How are these similar to or different from your own?
4. What characteristics do you see in this person that would characterize someone with whom you could get serious? (This is a heavy question but there must be at least one reason why you said yes.)
5. What characteristic do you have trouble with by overvaluing (i.e. looks, style, faith, car)?

Be honest with yourself with these questions. Be honest with your team. You are not judging this person into a category of “never-to-date-again.” You are trying to put words and thought as to why you said yes to this date. This is not about the date. This is about why you said yes.

After the date ask yourself these questions. Bring your team in on these questions too. They make for a great and directed conversation.

1. What did you learn about this person’s activities, interests and life passions?
2. What spiritual qualities does this person have? How are these similar to or different from your own?
3. What characteristics do you see in this person that would characterize someone with whom you could get serious?
4. What characteristics do you see in this person you definitely do not want to see in someone with whom you get serious?
5.  How do those qualities and characteristics affect you—positively and negatively?
6. Did you notice anything surprising about this person or yourself? If so, what is it?
7. How were you stretched?
8. What things might you have thought negatively about before now, upon closer inspection, look different?
9. Does this person remind you of any significant person in your life? Is that positive or negative?
10. What are your reactions to the person? Do you find yourself attracted? Why? Is it a sick or healthy attraction?
11. Are you romantically idealizing this person? Analyze why you are so instantly smitten.
12. Do you find yourself not attracted? Why? Is that a good thing or a bad thing?
13. Are you turned off because this person seems stable and “boring?” Compare that to your last relationship with someone whose life was characterized by chaos and risk taking when what you really longed for was someone whose life was stable. Now that you are looking at it, how does it seem? Is that good or bad?
14. Did this date discover a pattern in you?
15. What are your fears and insecurities with this person?
16. How were you not yourself with this person?
17. Do you open up or shut down around certain traits this person has?

Yes, this will be a long conversation after the date. But think of the things you will discover—in you! And that is what is important. You are learning about yourself. Brave dating is dating to discover who you are. Your team—with the specific use of these questions–is to help you not let your defenses and excuses keep you locked up in a small world.

This is getting exciting. We’ve gone from theory into application. You can do this. Be brave.

(Questions taken from How to Get a Date Worth Keeping, pp. 124-126, and adapted.)

(Photo credit:  Gratisography.com)