In Part II, I wrote: Ask questions! Not factual questions (“How do you get to work?”), or at least not mostly factual questions. Look, if you’re not just looking for sex or fun (which is sometimes the same thing), you want to plumb the depths, and quickly. Or at least I do, to fend off the Terrible Second Date. The questions below are in my toolbox. Whether I ask a couple or all of them depends on how the date is going. This method is especially good for those who are shy or reserved.

Though the subjects are serious, I don’t want to grill the guy or treat him to a check-the-boxes questionnaire. When it works, the questions lead to exchanges between us – hopefully he asks “What would you say?” –  leading to a more open dialogue. 

1. What is your besetting sin? This question is meant to be playful, not necessarily intimate.  I always start that off with “I’ll tell you what mine is. It’s envy! I’m a childishly envious person,” so they see what I mean. I’ve had some revealing answers to that question (“I tend to be too nice to the women in my life”), but it’s always fruitful. Too nice?? What does that mean?

2. What would your former wife or girlfriend say about you? How would she describe you? This can be interesting, because it forces the guy to put himself in his partner’s shoes (I’m tempted to add “for once”). But it doesn’t work for widowers, because – as I said in The Dating Profile blog post – the typical widower’s assumption is that he was both adoring and adored, and so you’ll likely get that view of him as adorable, at least in his own eyes. Exes, however, tend to be…well, less adoring, going on scathing. If he tells the truth, some of that might come out, in which case I follow up with “Is any of that true?”. And I sit back and enjoy the rest.

3.What are you like when you’re angry? You can tell a lot about someone’s emotional dynamics from this one. Of course, the response is not always true, but still. You can often tell when B.S. is in the air.

4. What do you worry about most? This could be not only about their emotional landscape, or factual troubles, but how they relate to the condition of the country and/or the world right now. Again, it’s telling to know how they respond to this.

5. How religious are you? Unless you don’t care at all, this can be  important. It is for me, because someone devoted to any religion is not right for me. Many say they are “not religious, but spiritual.” In that case, I want to know what that term means to them…a vague sense of something we don’t know out there? Meditation? Astrology? Something else?

6. What are your political beliefs? I always bring up controversial areas, such as the Presidential election, the war(s) in the Mideast, or sometimes specific issues, such as abortion and immigration. This is such a deal-breaker question for me, I often ask it early on. Not everyone is happy about that, which shows something I need to know.

In my decades of teaching, I would tell students that what I look for in a good essay or response to an exam question is not  information, but interesting ideas. They would crumple at the word “interesting”…what does interesting mean? What makes a point in an essay an interesting,? I say, “An interesting idea is a way of thinking about a problem or subject in a way that provokes my own thinking”. ChatGPT is not very good at it. It’s hard to define, but like the judge’s famous definition of pornography, I know it when I see it. Or hear it, on a date.

Image by Mohamed Hassan at http://www.Pixabay.com