Figuring out interesting questions in friendly or romantic conversations

Question

How can I figure out which questions are interesting and will be pleasant for the person to whom they are addressed to answer?

I am a person who has an extreme problem conveying what he wants to express. I am pedantic, repetitive, redundant, verbose, and inflexible. My thoughts simply run too fast and they overwhelm me. I have difficulty in choosing how to express myself and even choosing the words themselves, as fast as I think, I have had one too many university professors asking whether I ever get tired or whether I could stay away from so much analysis and details. I have boring interests and I tend to miss many social nuances (trying consciously to make up for it makes me question whether or not there is a nuance when in fact there is none and useless because I can just pick up some nuance I fail to interpret it in a social context). I am otherwise excellent in picking up and interpreting nuances in an Academic or purely Linguistical context. My interests are broad but restricted to practical or philosophical or both. I am not interested in discussing any shows or other art, unless it is a practical matter. I am not interested in particular observations in society but only in more universal social phenomena. I enjoy culture and arts but keep it to myself or have very succinct remarks. People call me obsessed, fixated, boring, or incommodious. The complete opposite of affable. And I can only admit so. All in all it makes me believe that I should not talk or at least restrict it as much as possible.

So I want to ask people questions that will please them to answer those questions and let them do the talking. I can't simply get a laundry list of interesting questions because each person has their own tastes.

Answer 1

To ask questions that most people will find pleasant and interesting to answer, make those questions about the person and their thoughts and experiences, not about the details of the topic.

For example, you mentioned you had two friends talking about driving cars. You don't have any experience with this, and you started asking them technical questions. Most people don't enjoy playing an encyclopedia; if the answer to your question can be looked up in some sort of reference, it's probably not a good conversational question.

A better approach would be to ask them something about their experiences, opinions, or feelings. If they're talking about how much they enjoy driving, you can say you've never been able to drive, and ask them what's makes it enjoyable. If they're complaining about their commute, but likely have experience with other forms of transportation, you could make a joke that at least they're not stuck biking in the rain or dealing with local crazies on the bus, or whatever is relevant in your area. The idea behind that sort of comment is to get them to give their thoughts on the relative merits of, say, biking versus driving. You might find out something like they really enjoy biking but can't do it anymore for some reason, or they do bike sometimes, or they'd like to but can't for logistical reasons.

That's not to say you can never ask a technical question, but it should be to facilitate the conversation, not as the main conversation itself. So if they tell a story that involves popping the clutch and you have no idea what that is, feel free to ask for clarification, but don't start asking for all the details about how a transmission works. Keep your questions relevant.

The same principle applies for starting a conversation. If you know nothing about the person, you can ask something general such as about their hobbies, if they've lived in the area long, what do they do for work, etc. If you know you have something in common (a friend, workplace, organisation), then you can start with that. Examples might be "so how did you meet Bob?" or "how'd you get involved with the book club?" If they say they met Bob playing trivia, then you can ask more about that: do they play often, are they any good, what's something cool they've won, and so on. If the last question you asked doesn't lead anywhere, then you can pick a different general question or go back to something they said earlier. For example, if they said they met Bob while playing trivia in Boston, but the trivia thread dies out, you can ask what they think of Boston.

To sum up, ask questions that will require an answer that involves the other person's thoughts, experiences, feelings, or opinions. Don't ask questions that only supply technical information unless it's needed to move the conversation forward on the current topic. If you could get the same info from Googling and you don't need it to understand what they're currently saying, don't ask about it. Feel free to add your own perspective so long as you stay on topic and don't monopolize the conversation.

Of course there are exceptions, you might find a gearhead who loves getting into the weeds about how engines work, but 99% of the time, this method is what you want.

Answer 2

I may be wrong but I assume people are described as difficult mostly when they talk too much or with sudden changes of topic, not when they talk/ask too little. I certainly don't know if this is true in your case, but you may want to focus more on (active) listening rather than your focus on questions.

So I want to ask people questions that will please them to answer those questions and let them do the talking.

When practicing active listening, you will first listen and understand, then ask questions related to what people previously said (which cannot be prepared). Those questions seem to be exactly what you are looking for: pleasant to answer and encouraging to talk more. When you 'master' active listening, you will only bring up your own experiences and interests when they are close to the topic the other person already talked about, and you will certainly avoid being seen as boring.

Answer 3

This is not an attempt at diagnosis, but the issues you describe sound very much like one particular aspect of autism spectrum differences. Autism spectrum is a complex condition that requires understanding far more about a person than what you've shared, and I'm not qualified to do that diagnosis even if you were wanting to share.

But it may be helpful to find resources for people on the autism spectrum to better understand social cues and behaviors. It doesn't take having enough elements of autism to find these sorts of resources helpful, it just takes having one of the facets of autism that is pertinent to these resources.

To be as clear about this as possible, autism is a collection of a couple dozen traits, each of which could be considered a survival advantage on its own, taken outside the context of the society we live in. But you get all of these traits together in one individual, and they'll have an immensely difficult time communicating with others.

I'm on spectrum, and I have the issue you describe to a very significant extent. My interests are very different from yours, but that is expected. Different people are different, and some of us are very different. (To be clear, I consider myself one of the very different ones, though mostly for reasons I haven't elaborated here.)

What I do:

• I focus on trying to listen rather than talk in conversational settings with people who don't know me. Once I've listened to someone enough, I tend to have a much better idea of the sorts of things they're interested in talking about. I'm not always good at just listening. Case in point, I'm typing up an answer right now, literally as I type this, and that's not listening or reading. But it does take a bit of a mix of listening and speaking to really learn.

• I try active listening techniques, as fruchti mentioned. Most of my listening is more passive, because I tend to find active listening to be frustrating. Also, figuring out the questions I need for it to be considered active listening requires quite a bit of work, too. That said, it tends to be a more efficient way to learn about someone's interests than passive listening.

• I use online resources to learn about people, such as reading prior and new questions (and the associated answers) on IPS SE, reading various reddit communities, including r/autism and r/aspergers.

• I talk with people I encounter out in the world at large more than most people I know. Note: I don't mean on the clock service workers, they have jobs to do. To a large extent, I mean street people, because they're around and have time. Of course, I've not been doing that lately, because quarantining myself for COVID-19 is important, especially because I'm immunocompromised and more than half way to the age range where it's most deadly. In talking to these people, my intent is to learn about them, not teach them about me.

• I accept that most people are going to think I'm weird. I mean, yeah, I am weird, so it's perfectly reasonable for them to think that. But the more I get to know more people, the more I wonder: are there any of us who are not weird?

I am, of course, still working on all of this, so I don't have any easy answers for you. This is just what I do.

Answer 4

You put forth a long heartfelt question about yourself, followed by four longish comments. From the outside, that looks lopsided. You understand and explain very well what you are expressing, although perhaps you find it hard to process what others are saying. Can you follow a melody?

That might be the reason you speak volumes (based on what you processed already), but interact with difficulty (based on not processing what you hear in the present).

Processing new information based on what you hear is the challenge. But in most conversations, folks are happy to do the explaining when you ask "Can you help me understand?" "Yeah, tell me more" or "Keep going."

When you say you want to prepare yourself beforehand for any specific situation, you are thinking about talking, not taking in what others say. Unfortunately, they may be picking up on just that. Talking at people does not look friendly.

It is generous to give freely as you do, and it also charitable to be receptive when others are doing the giving - when they speak. Be patient with other, be patient with yourself. Would you be able to try that?