One year he resolved to "do better about keeping up" - apparently feeling bad that our entire message history was him texting me a month before the convention asking if he could stay with me, and me saying that he could. True to his word, ever after that, he has periodically texted me every few months just to make idle conversation. He even stopped going to the convention but still keeps messaging me periodically - which I appreciate because it shows he didn't view me only as a hotel replacement.

Still, I prefer our old arrangement. Frankly, I don't need to know how he is doing every few months and I find it a bit awkward to make small talk any way. As I just have one friend that does this it's not so bad, but if I had more friends who wanted to just regularly "check in" like this, I'd have to start blocking people, ending friendships, or developing an automated routine to tell the curious that I'm doing well and to ask about their family and our mutual friends, etc.

There's a bit of secret sauce here that I tend to rely on to prevent myself from being considered "that guy".

First and foremost, I do this as much as possible via e-mail. Phone or WhatsApp is indeed too "personal" for these type of things (save for one person, an old boss of mine, who I have a scheduled zoom call with once a month. But that's just because he and I just like the chit-chat, it appears).

I write up a long-form message, something like 5-8 paragraphs with real news about myself and the things I've been up to, and ship that alongside the usual casual chit-chat.

It's surprisingly useful - I think this is the only context in which long-form e-mail is a good thing.

But then again, I grew up in an era where e-mail is the devil, and this was not always the case (or so they tell me).

Compare that to a text , where you might send a sentence or two and expect them to come back with something- when in fact, they weren't thinking about YOU and therefore aren't prepared to respond. Hence awkward.

Liking to write helps a lot with keeping in touch.

I think it is the other way round. People criticize it because "How to make friends" is the first and more prominent part of the title, while the book is not primarily about that. "How to influence people" fits the content much better than "How to win friends" but "influence" isn't the most appropriate word either and I guess that would not have sold the book nearly as well as its actual title.

Apart from that I think there is nothing to criticize about the content, it might be trivial to a degree, but it is solid and ethical advice, if I remember it correctly.

Exactly. I have this thing that I'm not good at. I have this tool I use to be better at it. Everybody wins.

One might say that computers in general are tools for computational work, since people are not as good at crunching numbers in their head at a consistent, repetitive and deterministic fashion over time.

One might even be right. :)

I would rather make a calendar invite / use <insert your fav software> and remember to call <valued loved one or friend> and feel bad about having to do that...

Then forget to call and feel worse about forgetting.

This. I feel really, really guilty if I hear something great or awful happened to someone I used to be in touch with, but the relationship faded away into the flow of life.

Why wasn't I there? What? It's been 3 years since we last talked? How did that happen?

So, no to all that jazz. Enter Monica. :)

Improving social skills and using them manipulatively are entirely different things. If you've ever known or worked with psychopaths you'll get that immediately. I suppose there's a continuum but still.

As many things, influencing people isn't inherently bad, but depends on how and why.

And it also says "Charles Manson used what he learned from the book in prison to manipulate women into killing on his behalf" but I don't know if that can be blamed on the book.

This is unfortunate.