After age 35, many seem to no longer believe in the term “soulmate,” and indeed I understand how over time– especially after suffering immense disappointment or loss– we may find ourselves in the singles scene losing faith in this notion that there may be anyone left out there that will ever connect with us deeply and care about our essence.  A kindred spirit is very hard to find, and it requires a lot of patience, something many of us tend to lack these days.   But every once in a blue moon, you may run across that rare gem in the dating world that is still looking for something far more meaningful than the rest of the herd.  How can you tell?  By the questions s/he asks while playing 20 questions.

When you are looking for a playmate, in other words someone to just have fun with and pass the time, a typical series of questions will including the following:

1. What’s your work schedule like?
2. What do you do for fun?
3. Do you like to travel?
4. What sports do you like?
5. Do you enjoy concerts, museums, plays, movies?
6. Where do you like to hang out?
7. What are your favorite restaurants?
8. Are you done having kids?

See how with these 8 questions alone, I am quickly able to decipher (1) if someone has the time and inclination to have fun, (2) whether they are done breeding, and (3) if our interests line up so we can have a good time.  Easy– complete all eight answers correctly within the first date, and you might well have a match for a playmate, assuming of course the chemistry is also there.

Now, if you are searching for a deeper connection, the questions will not be so easy.  They will take some time and thought in order to get to your core values.  More than just sizing up your brain, these inquires are trying to assess your heart’s capacity for empathy and compassion.  I could give you some of my favorite examples, but I would prefer if you came up with these questions on your own, for even the questions you ask reveal an immense amount about you personally.

Truth be told, playing 20 questions is a piece of cake after you get a few practice rounds under your belt the way it is normally played, with someone looking for a playmate.  It has been many, many years, however, since I have encountered one willing and/or able to play this game at a much higher level, where he would have the ability and desire to bear his soul.  Sadly, many seem to have either lost or sold their souls and all that remains is an empty shell, and this becomes apparent right away when you try to dig deep.  These people will either shut down, get angry or try to deflect your attention else where.  My advice would be not to press, but gracefully move on.

Learning to compartmentalize is a skill many can learn to perfect in the dating game, and I am truly not here to pass judgment or advocate for any right or wrong way to proceed, but I do want people to be aware of the fact that there is a major difference between how you play when looking for a playmate versus looking for a soulmate.   What you are looking for will drive the questions you ask, and let me just say playmates are a dime a dozen, and there are very predictable rules to help you along in the game. But, when someone is playing at a higher level of 20 questions, all the typical rules can and often do go out the window.  These rule benders are rare, and waiting for one to drop into your lap requires having tremendous patience and believing that good things come to those that wait.

By Regina A. DeMeo, Esq.