Even with the right questions conversation may not flow quite as freely as you may hope. That's because you need to really listen actively to the answers that you get. A conversation is like a tennis match, with words flowing back and forth like the tennis ball.
Carefully listening to the answers you are given will give you another idea to pick up on which should lead you to another question and from there, you can progress the conversation, whatever your purposes is. If you listen carefully to the answers to your questions, conversation gets a lot easier and a lot more productive.
However, it is true that if you have some good, interesting questions conversations flow more easily than if you asked closed questions requiring a yes / no answer or boring questions that yield uninspiring answers or perhaps worst of all, if you asked embarrassing questions which make your listener clam up in silence, not wanting to answer you.
You can avoid all of those pitfalls with the following questions:
1. If you could live at any time in history, when would it be?
This will help you to see what qualities the person admires and what they would like to do with their lives, such as politics, theatre, movies etc.
2. If you were asked to do so, would you sing in public?
Again, you will find out something of the person's interests; you will also probably find out if they can sing or if they want to be able to, so perhaps you will uncover a shared passion for music. Also, you may well find out how shy or extrovert someone is, which will give you an idea of how to handle the rest of the conversation.
3. What are you passionate about? What really moves you?
This question has the advantage of having an element of surprise as people are not usually expecting this sort of question, but it tends not to embarrass them or put them on the spot because they can answer lightly with something like 'watching my baseball team win a game 'or a similar answer.
4. If you won the lottery, how would you spend the money?
With this question you will find out what motivates the person, what they like to spend their money on and also something of their attitudes towards their significant other; of course, you might also find out if they have partners and children you do not know about!
5. What is the craziest thing you've ever done?
People might lie about this, but they will feel free to have some fun about it; it does not even matter if they lie, since whatever answer they give is sure to lead on to further conversation, whether what they reply is really crazy or not.
6. If you were throwing a party for five people, who would you invite?
These might be a mixture of famous people and people important to them in their life. Whoever they say will lead on to further conversation about why these guests were chosen and how your choices match up.
7. If time and money was no object, to what causes would you dedicate your efforts?
This can tell you a lot about a person's passions.
8. What if your favorite comfort food meal?
This can lead to some great nostalgia and a trip down memory lane to uncover the associations as well as to swap recipes.
9. If you could pick one talent that you do not already have, what would it be?
You'll find out about a person's passions this way. And if you happen to possess the skill they wish to possess, why not offer to teach them?
10. If you could spend a whole day doing exactly as you wished with no demands and no responsibilities, what would you do?
People dream of those kinds of days and they will usually love to share these ideas. You'll really find what people enjoy doing with a question like this.
If you are communicating with a person online, you could also ask them to explain the reasons behind their screen name.
You will probably only need to use one or two of these questions in any situation. Remember that initiating conversation is the aim of these questions; conversation entails you properly listening to the answers that you are given and picking up on those answers to progress what you talk about.