How to address issue of friend not replying to specific questions

Question

Background:

I have a friend named "Joe". When talking to him through messages it feels like he drops off mid conversation. On several occasions I asked him a direct question like "when are you back from vacation" he doesn't reply at all. He replies to the next question. Other people notice he does this as well. Another example was he told me he liked his new home and how it's a lot different than his old one. I asked different in what way and he never replied.

What I tried:

when I was with him I told him I find it rude when someone does not answer a direct question. He agreed. I mentioned I feel like he sometimes doesn't reply to my question. He said "when did this happen?". The only example I could think of in the moment he had a valid explanation for so it wasn't really constructive.

Considered:

It was him that got this friends group into using a specific messaging app he likes. It supports read receipts but he has his turned off. I'm wondering if all this is some sort glitch and he isn't getting some messages. I've waited days and got no answer.

What I am looking for:

Without making him feel defensive how can I find out why he doesn't respond? If it's a technical problem maybe it can be easily fixed. If he prefers phone calls, that is fine. If he doesn't like talking about certain subjects, I would like to know the subjects so I can avoid them.

I am looking for answers with actionable advice. Please don't reply with "this isn't possible" or "you can't do this". Thanks.

Answer 1

There are many reasons why a person might not answer a direct question like "when are you back from vacation?" As you've suggested, they might not have seen it. They may have been distracted by some other thing you said (or something in their environment) and just forgotten the question. Or they may actually not want to answer it. After all, your friend does not have some sort of legal obligation to answer any old thing it occurs to you to ask, right?

What I do in this situation is to ask again, but in a different way. Don't just repeat the same words. There are two reasons for this: first, if they did see/hear the first question, repeating it word for word will be seen as rude. And second, adding more information will increase the chances you get an answer if the person was choosing not to answer.

Example:

you: stuff

you: when are you back from vacation?

you: stuff

them: answers stuff but no mention of vacation

you: I was wondering if you would be back from vacation by Friday or not, because I wanted you to come and watch the game with us

The extra information gives them a reason to answer. In fact, I have a general "give before you take" rule that recommends giving people a piece of information before asking them a direct question. Not every time -- the normal ebb and flow of conversation includes plenty of short direct questions -- but if someone seems to be ducking or ignoring a question, add more information when you ask it again, in order to encourage an answer.

In general, coming to someone to complain about a behaviour you think they do a lot doesn't work. People just say "I don't do that", as you've seen. Instead, react when it happens. If you don't feel like asking again with more information, you can "go meta" and say "is there a reason you don't want to tell me when you're coming back?" -- you say you want to know what topics your friend doesn't want to discuss, and this could help with that.