How to ask questions on dates

I was watching a Matthew Hussey video recently (Please don’t judge me…) and in it he spent quite some time talking about building a connection using questions. He used an analogy about not wanting it to be like a tennis match of questions and answers and more like a football game of keepie-uppies. Now, weirdly I’ve never been any good at all at doing kick-ups, but questions? Those I can do.

For about twenty years I’ve been a facilitator for group sessions and consultations, a job which requires knowing the process, knowing the people and trying to know nothing about the subject matter. You see, the more you know about something the more opinions on it you already have, so the more your questions focus in one area or become leading. Trying to maintain no preconceived notions about what something “already is” or “should be” means you’re much more likely to actually discover the truth about it.

When I was training other facilitators I taught them about three different types of questions that they should have in their arsenal and know when to use and when to avoid them. Yes, there are other theories about question types, but three seemed like a good number so made it easy to remember. They’re pretty simple concepts, and ones which on reflection also sit really comfortably in the world of dating.

Those early chats and dates are always challenging, after all. Part getting to know them, part trying to put the best version of yourself across and also part discovering what the two of you are like together, early interactions can be scary. Whilst sometimes conversation just flows as if you’d known them all your life, other times it takes a little bit of questioning to build up a rhythm or find the subjects around which you can engage.

A good questioner will use all three of these types of questions throughout a conversation, whether that’s face to face or digitally, and will be able to learn different things as a result of each of them. Use too many of one and things very quickly go off track; as with all good things it’s all about balance and blend.

1 – Closed questions.

Closed questions are by far and away the easiest and most commonly used questions in any conversation. They are also probably the least useful and most disappointing to be part of. Closed questions close an answer down to a single word, a single phrase or a single idea, and can often close off a conversation entirely. Some examples include:

Are you going away anywhere on holiday this year?

Do you like seafood?

When’s your birthday?

It might seem that you are opening up a world of potential with some of these, but all too often you find yourself hearing “Yeah, I’m going to Greece actually.” or “No, not really.” or “September.”

Each of these is finished with a full stop because for some people they have simply answered the question. They aren’t able to sense when you’re giving them the opportunity to open up a little more, explaining how you’ve always wanted to go to Greece as you’re fascinated with Greek mythology, or how you once talked your way onto a fishing boat in Goa and ended up choosing your pick of the catch and getting the hotel to fry it up for breakfast, or that you think you’re going to treat yourself to a record player this year as you’ve got a stack of old soul LPs gathering dust and quite like the ritual of putting a physical record on to play.

No, for many people it’ll be their chance to answer it, maybe following with a weak “how about you?” before moving onto the next closed question.

On the bad side, this is boring. It creates no flow whatsoever, and gives you nothing to work with. No-one likes an awkward silence, especially not with someone you’re trying to get ot know. But what it does do is show you an element of their personality and whether they’re compatible with you communicatively.

If they close everything down then either they don’t have the skills to communicate with you, or alternatively they don’t want to. Used sparingly, this can be a really useful tool to look at compatibility. Just watch out for yourself and whether you find yourself being the one closing things down – could be a sign that you’re not as into them as you thought.

Open questions

Open questions, on the other hand, are far more interesting. They are set up in a way which allows the other person to answer freely and at more length, and encourage them to elaborate rather than give short or even monosyllabic replies. They might look like:

What do you think about Love Island?

I absolutely love Japanese art, would you ever go to a manga exhibition?

If you could have a ticket to anywhere in the world, where would you go tomorrow and why?

Some of these may be cheesy, but they open up the conversation in a way that a yes/no answer doesn’t. They can reveal parts of your personality or likes and dislikes and ask for them to share theirs, but without setting out what you are expecting the answers to be.

You can then discover loads about them from how they answer, what they say and whether they’re speaking from the heart or not. If it’s something they’re passionate about you’ll be able to see it in their eyes; there is nothing more interesting or sexy than someone showing some passion for something, even if you have little idea what they’re talking about.

The only problem with asking only open questions is that they rarely give you a single answer. Sometimes a little information is all you need; if you need a simple answer then ask a simple question.

Leading questions

Leading questions are the most dangerous type of question there is. Formed as if it were a question, it actually tells the other person what you think the answer should be and encourages them to agree with you. Humans are herd animals after all, and if someone likes you and knows that in order to get on your good side they simply have to agree with you then they will, regardless of whether or not it’s their actual opinion.

Horoscopes and astrology is just a load of rubbish and mumbo jumbo, isn’t it? Nearly as bad as homeopathy, right?

I can’t stand vegans, they’re just the worst, aren’t they?

Surely you can’t still believe in true love?

Of course a strong person will give you their real opinion regardless, but they may temper it if they think it will harm their chances with you. It also runs the risk of you revealing something of yourself which may push them away – again, this might be useful on occasion but there are definitely better ways of doing it.

Of course, if you are playing a little devil’s advocate, or playfully bantering away and being flirtatiously provocative then it can be perfectly fine to do this – you just need to be very sure the other person knows it too.

At the end of the day, what you’re aiming for is the start of a conversation, exploring little bits of ideas, experiences, values, history and more to start getting a more rounded view of someone and share a view of yourself. It’s not a police interview, nor is it an interrogation of any kind; it needs to be playful, fun and flirtatious while also revealing more than you’d get from reading their bio.

Use a combination of all of these question types and you’ll be far more likely to have a good time and get to know them, and that’s what you really want, isn’t it?

(Two points if you spotted that final leading question, by the way)