What questions should I ask on a first date?

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The worst thing that may happen on a first date is that the conversation peters out and you suddenly do not know what to say. There is of course a whole range of strategies to get over this problem or still better, to simply avoid getting into this situation.

While the ideal conversation topic for a date simply does not exist (What Do I Talk About on the First Date), it really does help if you prepare yourself in advance and think a little about how to lead an interesting conversation with other people. There is quite a lot of literature available on this topic: classic examples with continuing success are “How To Win Friends and Influence People” by Dale Carnegie (

Especially Carnegie points out something that is immensely important in every conversation: having an honest interest in the other person.

Spending long minutes staring at her boobs is not only stupid but will also destroy any chances you have with her. The questions you should ask on a date are those arising from a sincere interest – which is very easy, because if you are really interested in her and her life, the questions will come up by themselves, with no effort at all on your part, and all of a sudden you will notice that you have created a mutual feeling of having a special connection between you. And this happens without any tricks at all, and on top, with a lot of fun for you.

The point is -of course- not to conduct an interview, but to be as casual and natural as possible. The conversation has to develop by itself. You take up something mentioned a few moments ago and build up on it, step by step. What is most attractive is to show that you are interested, but without taking everything being said too seriously, amusing yourself at the same time.

We can therefore conclude that such a conversation is always a balancing act, switching back and forth from humour to seriousness, with a little arrogance thrown in-between. An exciting situation arises with is never boring but very interesting and funny, is generated this way. Serious issues and discussions should be avoided. Also never try to be the entertaining clown, because it is very difficult to get rid of this unattractive image, and it will be very difficult to take control of the conversation again.

The saying “Practice makes perfect” also holds true here: whoever is able to converse with the janitor, the boss, the neighbours or the fellow passengers on a train, can do the same with the woman of his dreams.

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