Boss inquisitiveness

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I have had a tendency to have bosses who are overly inquisitive, or invasive of my privacy, about matters which are very personal to me, and nothing to do with the job.

I've realised a common theme is asking questions or investigating what I get up to on the Internet in my spare time. I was recently asked by my current boss about my Asperger activities, leading to questions about my Asperger friends, leading to questions about what one of them does as hobbies, leading to a request to see some of his material (as writing's his hobby) which is online on a blog.

It's funny how people are so intuitive that they follow a line of questioning in a way that leads straight to your most deeply personal, private affairs, as if they can read your mind.

I find it impossible to refuse such requests since I consider it important to be as open in communication as possible with a boss, given that boss communication is challenging for me, that job insecurity is well above average for me, and that they ultimately, and at least temporarily, give you a level of security that you wouldn't have if you didn't have a job.

I find the situation very worrying especially as it isn't even the only time I've ended up having to give up material from the SAME guy to a manager in this same job after they directed conversation a certain way.

If I'm understanding correctly some plans I was recently asked to type up, I'm losing my job soon. This concurs with the fact with a manager recently telling me there'll be job restructuring with implications for admin (and I'm admin). Could this sort of knowledge of private, non-work related affairs contribute to people's redundancies or sackings?

In a previous job I was asked to give details of a webpage I had to a manager so he could go and look at it, which was about a deeply personal private matter to me (and anonymous).

In a job prior to that, I was once questioned by my boss about my private internet usage, who I was contacting, where they were, what sort of conversations I was having, etc.

Anyone else been in similar situations and how have you negotiated it?

There are several things you can do about it. One is publish your stuff you want to keep from employers under a pseudodynm and publish sanitized stuff under your real identity. Of course in doing this, you will have to scrub your previous postings as much as possible.

Another way to deal with this is to ask your boss why he or she is interested. This can be done casually ("Why do you want to know that?") or it can be done in a way to put off further inquiry ("Are you into me?" or "I didn't know you liked me so much"). One thing that the boss can be testing is your metal or if you will give into unreasonable demands. Someone who is overly compliant may be a good person to manipulate to use as a scapegoat or to do some dirty deed.

To begin with it sounded like small talk to me, like he was trying to take an interest in something you could both relate to asking about your friends writing but the end of your post sounds totally different. Why on earth would your boss need to know that kind of thing?

this sentence is what I'm talking about. When a boss asks you questions like this it usually means he knows the answers and is trying to see if you'd hide the info. You can of course tell him to sling his hook.
I'd avoid asking your boss if he's 'into you' lol it may sound humorous but not everyone would take it that way. You can find out why he wants to know so much indirectly by asking questions such as if he is interested in the subjects himself and what he thinks of them. Ultimately you'd be best not using work internet for things you're not comfortable with people knowing about, use your phone or something. If it's home internet usage and it's nothing illegal tell him to beat it. if it's illegal or reflects poorly on the company (as in anti-social behavior, booze and drugs or misappropriation of funds or equipment ) then you might have a problem, anything else is discrimination surely?