10 Questions To Ask On A First Date That Reveal If You’re Truly Compatible

If you’re in the market for a committed relationship, then working out what set of problems you are signing up for early on is smart.

Philosopher Alain de Botton said that in a wiser society than our own, one standard question on any early dinner date would be: ‘and how are you crazy?’

What other conversations could we have?

Along with practical things (who wants kids, extent of prospective in-law interaction), we want to see evidence of character traits that are going to be our most useful allies in the relationship.

And we want to notice those stumbling blocks, too.

Does this person show signs of a healthy self-esteem; a smattering of self-awareness? What particular brand of monster do they become when they are hurt or disappointed?

Far be it from pessimistic, this level of pragmatism may be more romantic than we give it credit for. A partnership between two individuals that have acknowledged their flaws up front, and said ‘yes, please’ anyway represents true choice — something characteristically lacking in the couple that got it together because of loneliness or delusion.

Here are 10 good conversations for those first dinner/drinks dates.

1. What do you do, that you don’t like doing, for a long-term gratification?

This one gets to grit, which you need if you are intending on having a Long Term Relationship (‘LTR’).

Are they disciplined with exercise and their diets? Do they do a painstakingly tedious job whilst they move towards realizing their vision?

If a person’s stomach for the emotionally uncomfortable isn’t on an even keel with yours, you may lose respect for them. Plus, that lack of resolve signals their approach to handling the difficult periods in the relationship.

2. What are your biggest vices?

Obviously, nobody’s perfect. However, the brand of our particular imperfection matters.

If your date is still dealing with material world vices — drugs, food and alcohol — while you have graduated onto mastering your psychological vices, it probably isn’t going to pan out.

3. How do you deal with disagreements?

How’s their self-awareness? Are they mean or angry when stressed and upset, or do they spiral into shame? How is their disagreement style? Are they partial to a spot of impassioned raging, or are they more measured, cool and calculating?

How well you can argue as a couple will determine the length of the fallout period following the inevitable breakdowns.

4. What do you believe about relationships?

Everyone has something they believe about meeting the person of their dreams. It could even be something as prosaic as ‘not through Tinder’, which makes meeting you on Tinder an extra mental obstacle for them to get over before they take you seriously.

5. What has your experience with your exes taught you?

How responsible are they for their choices? Are they still playing the blame game with an ex? Are they going to do the same thing with you each time you mess up?

6. What did your parents get right and wrong?

Not everyone from a broken home is damaged about relationships. Similarly, not everyone birthed from a Brady bunch style arrangement will be entirely relationship well-adjusted. However, anyone with an inquiring mind has formed an opinion from their first example of a LTR. What’s theirs?

7. What frustrates you the most about others?

In others words, what will they try to hide from you the most? Ideally you’d prefer it if they were familiar with the concepts of projection and shadow work — but that’s probably asking too much.

8. What do you do just for you each day?

Are they taking their happiness into their own hands? If they are proactive about their emotional wellbeing, then you can rely on there being a similar proactivity in the relationship. If they are planning on delegating that function to you, then things are going to get ugly fast.

9. What do you value the most in your friends?

In other words, is there a solid basis for a friendship there? Is there substance? Will they still be amused by you after the honeymoon period sexathon steadies to something more steadier paced?

10. What do you believe about your beliefs?

Having beliefs is okay — provided that we aren’t taking ours too seriously.

If they’re gripping theirs with vice like strength, then not only might they embarrass you at dinner parties, but that psychological inflexibility is going to ooze into your communications. A little humility goes a long way.

Assuming that we know what we want, then bringing a little more intentionality to those early dates is no bad thing. These conversations are a good place to start.