I've been noticing recently that I have terrible trouble using e-mail (or its close equivalent, Mono messages) in a conversational context.

I think it's because I mostly see e-mail as a means of getting a job done; it's a businesslike medium, used to send instructions, questions, answers, acknowledgments, and in general information that people need for some reason or another. Therefore, I tend to keep my messages to the point, answering precisely the questions asked.

So when someone sends me a message on Mono asking ‘How are you?’, my immediate instinct is to respond with a paragraph or two telling them how I am, and nothing more. Typically a few seconds after I send that message, I suddenly remember that this is a conversation, and that therefore it's entirely appropriate to ask ‘How are you?’ at the end of the message, so I send a hurried follow-up with that.

And when a friend sends me angsty mail about their life problems, I often find myself completely at a loss as to how to respond. In person, if I had nothing helpful to contribute, there'd be a whole range of appropriate responses: nods, grunts of acknowledgement, sympathetic looks, hugs etc, to reassure the person that at least I was listening and I cared even if I didn't have any concrete help to offer. In email I find this dreadfully awkward and quite often will fail to respond to such a mail if I don't have any actual content (as some part of my brain sees it) to contribute. A couple of weeks ago this caused someone to assume I didn't want to talk to them, which suggests that it's something I ought to work on solving…

I wonder if it might be about silence. In a face-to-face conversation, long silences feel very awkward, so one naturally brings up additional topics, starts new threads, etc, so that the conversation continues. But in email, long silences are perfectly normal. It's fundamentally interrupt-based: you get an email, answer it, and go back to what you were doing, and because turnaround time is often hours or days, you don't spend your time doing nothing but wait for the reply. So if the reply takes a bit longer, that's normal and you just find something else to do; and if the reply never arrives at all, it's often not something you'll even notice unless you were genuinely depending on it for something.