Tips on Asking Questions to Guys

Specific information.

Asking questions for specific information can be a very direct thing, such as Do you have a girlfriend? or it can be an indirect thing What does your girlfriend think about (whatever)?. In both situations here you might be simply trying to find out if the boy has a girlfriend, but one of them hides your intentions (albeit not very subtly).

If you dont want to hide your intentions then just ask away, that is the easiest way to get information!

If you dont wish to make it clear what you are thinking, you can be more sneaky.

For example, you want to know Why doesnt he have a job right now? but you would prefer to be less direct, you could instead ask What are your career plans right now?

Another practice for asking questions in order to get specific information, is the art of asking leading questions. You might not be able to just ask somebody outright Are you dating anybody? without it being too uncomfortable, but you can lead into it with other questions. See below for an example of this:

What do you like to do for fun? -> What do you usually do on weekends? -> Oh, you are single then?.
The number of leading questions can be increased or reduced depending on answers. In the first answer, you might get I like to hang out with my girlfriend. Or you could get I like to as your first answer, who knows.

Making Conversation

Sometimes we just ask questions simply to keep the conversation going. Unfortunately, these questions are often generic and boring, and dont follow on from one another. The worst thing you can do is ask somebody a question, then ask them another question almost immediately afterwards that has nothing to do with the previous question. See below:

Question 1: So what do you like to do for fun?

Answer: Well, I like to play tennis on weekends and see movies if I get a chance

Question 2: Oh ok, so whats your favorite colour?

You might think this looks ridiculously obvious not to do this, but I have seen it happen many times before, as the person being asked
the questions. It can be incredibly annoying. A much better method would be to ask follow-up questions that are relevant to the previous answer. See below:

Question 1: So what do you like to do for fun?

Answer: Well, I like to play tennis on weekends and see movies if I get a chance

Question 2: Really? Cool, do you just play tennis for fun, or do you enter competitions?

Answer: I used to be quite competitive but it is mostly for fun now

Question 3: Oh, did you ever win anything?

and so on. See how much better this feels? Not only is the person you are talking to going to think you are actually interested in them, but they are going to respect you more for being a better listener. You might even get invited to play tennis with them sometime. Following conversation formats like this allows for a much deeper connection and a more enjoyable experience.

We dont just want to compile the best list of questions to ask, we want to explore the reasoning behind them.

Two final tips on asking questions to guys.

1. Be prepared to answer your own questions, if the guy says How about you? after answering, you would do well to answer it.

2. Ask follow-up questions about his answers, dont just keep firing off questions that are unrelated or it will sound like you are just reciting a list and not really interested in his answers.