Someone once said “The best time to dig a well is before you get thirsty”. Sound advice that applies to the Dating, Love and Marriage World, insofar it is useful to hold some useful questions in mind as you go.

Part of me is tempted to say, just go out and enjoy your Date and forget the questions, and for sure there is a place for that, if you are definitely not interested in an ongoing committed relationship. If you are looking for something a bit more meaningful and longer term, then best you are a bit more hard nosed about it. Let’s face it you wouldn’t go out looking for accommodation or a car to buy without having some idea of what you want.

Here are some questions to consider when you are out and about with your latest Date.

1: Would you like to be like the person you’re dating?

If the answer is no, why are you dating them? Take note of your answer to that question. What is it exactly that you don’t like about them and stop and think is there some aspect of that about you? Asking yourself these questions can give you a lot of information about yourself and about the person that you’re dating. We are drawn to people for all kinds of unconscious reasons. It’s good to make this conscious.

2: What is it that attracts you to this person?

Is it just their looks or their hot body, their car, perhaps their status? All of these things are superficial and remember all that glitters is not gold. These things do not make a sound foundation for long term relationships. Why is it that you tend to be attracted more by these superficial traits rather than character traits such as kindness and social awareness? Could it be that you are still at the stage of development where you care more about impressing your friends? How about choosing the character traits you most like in a person and make that your yardstick for choosing.

3: Do you know your core values so that you can check out if your date shares them?

This is really crucial. For example, if you love to read and enjoy learning and your date wouldn’t know a book if it jumped up and bit him, it can make a real mismatch further down the line and if you feel like you have to apologise for spending your leisure time on personal development or reading or learning, then it’s useful to get clear about your core values in the early days. Your core values are like having a compass on a foggy moor.

This is like keeping the screen wash topped up in your car, so that when the screen gets cloudy you can see where you are going. It’s important to know your core values for making sure that your decision making in all areas of your life is built on what really matters to you. It saves you from going off course.

4: Are you being blinded by the chemistry?

We all know how wonderful it feels when you first fall in love, but when you engage in sexual activities soon after beginning to date someone, it’s easy to start seeing them through rose coloured spectacles because you’re full of oxytocin, vasopressin, dopamine and all that bonding chemicals makes you feel good.

Now don’t get me wrong, there isn’t anything wrong with chemistry and it’s good to enjoy it but don’t forget that it’s there and don’t forget that in effect it creates an illusion, so it’s no wonder that many people finish up feeling disillusion. This is how you finish up seeing them through rose coloured spectacles and you overlook negative aspects of their personality and you magnify positive aspects of their personality, so just remember you can get a distorted view. It is wise not to make any longer term decisions for at least 6 months when you are both a bit more grounded.

5: Is this person reliable and trustworthy?

Is your Date the sort who is willing to commit to a relationship with you or with anyone? This is something that you can only learn over time by observing how they interact and conduct their affairs with other people and how they operate in different situations with different people.

For example, how do they treat waiters in restaurants, how do they treat cashiers in shops and supermarkets, how are they with their family members and their friends, how are they with their work colleagues? You really need to see them in these different settings to see how reliable are they and are they to be trusted. Do they keep their word, do what they say they are going to do? Notice if they have long standing friendships, if not, why not?

6: How does their family get along?

What are the patterns and customs that your Date’s family has? Listen out, take note and ask questions. How do the family members treat each other? The late, great family therapist Virginia Satir reckoned that more than 90% of families were dysfunctional. So we’re not looking for perfect families here but there are degrees of wackiness and it is useful to see how your date’s family operates before you get any further involvement. Many people find themselves married to an alcoholic because they believed their Date definitely would never be like his alcoholic father whom he despised.

It’s useful for example to know what does it mean by “I have a very close family”. Does that mean that they spend absolutely every Christmas, Easter and birthday together and as years roll by you’ll be an outcast if you want to spend some time with your own family. Believe me, I have seen this happen.

So it is useful to know are there any family situations that can cause long term effects. Has there been addictions, mental illness, early hospitalisations, a number of family situations it’s worth finding out about. We’re not looking for perfection here but you need to be able to know what it is that you might be hooking up to.

7: What is their attitude about money?

Do they have any? Do they spend it, save it or do they have a good balance of both? Many clients I see discover when they are almost married that their partner has a mountain of debt that they knew nothing about. Why, I ask. Well they didn’t like to ask. Can you believe that?

If you’ve got any intention of spending a lifetime with someone or anyone, best you get used to asking pertinent questions. It’s totally reasonable to know about a potential spouse’s bank balance and to be able to discuss the subjects of money, sex and children because they are the three things that most people get into conflict about and you need to be able to discuss these subjects with them.

No. 8: Does this person have a vision for what kind of life they want to live or have they never even considered it?

Have you? What do you want? Do you know what you want? Why not? How do you expect other people to know what you want if you don’t know? Do you want to travel the world or do you want to settle down and start a family or do you want to do both? Would you ideally want to be more family focused or maybe your Date wants to emigrate to Australia and you might want to do that too and that’s OK but it’s useful to discuss these things. This is why identifying core values is important but it’s also good to know if you share any joint or reasonably compatible aspirations.

There was a popular musical film around when I was young called South Pacific, one of the lines in one of the song lyrics was “you’ve got to have a dream, if you don’t have a dream, how you gonna have a dream come true?”

The fact is we all create our own reality, so if you are going to have a dream, have a big one. If you don’t have a Vision or don’t know what you want, I encourage you to engage the services of a Professional Coach.

9: Does this person bring out the best or the worst in you?

Do you find yourself at ease with them, happy in your own skin, is there a fit between you both? Some couples, lovely as they are, simply do not fit. Most people do not understand that it is part of every intimate relationship to trigger unresolved hurts wounds and insecurities from the past in each other, mostly unwittingly, but that’s why in time the relationship needs to be able to accommodate discussion of these issues and you should feel supported and at least at ease about discussing areas of vulnerability. Do you find yourself getting irritated or angry around them? That of course will say a lot about your patience and tolerance levels, but as Desiderata says, avoid people who are a vexation to the Spirit.

10: Have you met their Mr Hyde yet?

We all have our Mr Hyde, or dark Shadow side, where the rejected and unloved aspects of ourselves and our history hang out, and that operate unconsciously. Other people can see it, but we can’t. They are a real part of the baggage that everyone has and it’s a huge mistake to be unaware of it or to decide to keep it hidden. It will create a wall between you and prevent you both being emotionally honest. Without emotional honesty there’s no real intimacy. The danger of not understanding this is that we all tend to project our denied aspects onto other people and see in them what is actually in ourselves. It is useful to be able to ask your Date about what kind of things they tend to feel angry about and how do they react. Forewarned is forearmed!

I hope you’ll keep these 10 questions in mind as you go through time with your Date. Remember it’s good to follow your heart but please take your brain with you.

Grace Chatting has a professional background in Social Work with children and families. She is MBACP Snr. Accredited Psychotherapist, Family Mediator, Relationship Coach, Founder of Relationship Academy and Author of the book “Mend It Don’t End It” Grace can be contacted on 44(0)7816491165 or by Email

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