The dilemma of asking a personal question

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Many times when I read a guide on how to make friends, this idea of showing interest in the other person shows up.
I understand that humans have a drive to 'feel important', and I can be genuinely interested in others, the trouble is that I am always unsure of what is an appropriate personal question to ask

I know that questions such as 'What's your salary' or 'Are you gay' are NOT appropriate. But I find that very hard to tell from context and the person's communication if they are ok with 'What did you do over the weekend' 'Did you like your holiday', and it gets especially complicated after you've known the person long enough that you already know the basics such as 'what school did you go to' 'do you like your job etc'.
I find it specially tricky because I am a naturally quite open person, and here in southern England people tend to be very guarded and impersonal even in social occasions outside work etc.

Welcome to WP. It can be very tricky. I suggest asking as little as possible. Just enjoy whatever you happen to be doing together.

Prefacing a question with a disclaimer such as, "I hope I'm not being too nosy, but I was curious about..."

General questions can be better than specific ones such as "what sort of vacations do you enjoy" might be more welcome that "where did you go on your last vacation".

I guess one workaround would be to put out feelers rather than put them on the spot with a direct question that they can't dodge without looking rude. I don't know of anybody who would feel uncomfortable if asked what their job was, in fact a lot of people seem keen to talk about that. And "how was your holiday?" can be sidestepped by "oh, not bad, how was yours?" though again if they enjoyed their holiday then they'd likely want to talk about what they enjoyed. And "did you do anything nice over the weekend?" is also fairly easy to be unforthcoming about with "nothing very exciting, bit of telly, bit of football, bit of shopping." I agree it's rather personal to ask them about their sexual orientation if you're not close. And income is often something they like to keep secret, though I can't think of an innocent reason why they would. It seems strange that people so often do these resource displays to advertise how much they can afford to waste, as if they want us to know they're wealthy but they don't want us to know exactly how wealthy. Maybe if the income is low they're embarrassed to admit it, though the economic system can easily turn people into paupers through no fault of their own and it's rather a myth that it's your own fault if you're struggling to pay the bills.

My own failing is that I hardly ever remember to ask any questions at all, and even when I do remember, I can rarely think of any in the heat of the moment. So people probably think I'm not interested in them, which is only partly true.

I agree that people tend to have a strong drive to feel important, though for me importance is like money - I'm fine with somebody not wanting less of it than average, but if they can't be content with equality and expect to feel like they're part of some elite class of admired VIPs, I think that's just greedy, and rather stupid. For me, everybody's important or nobody is, and I don't admire people as individuals, I only admire some of their traits, not the whole person, that would be ridiculous. No doubt that annoys people who expect me to revere them, but I can do without egomaniacs in my life, and they know where the exit door is.

This is my main social awkwardness. I feel that if I ask a personal question I'm being nosy, but if I don't ask them I'm being aloof or disinterested.

Sometimes it helps if I can imagine the other person asking me the same question in the same situation. For example last week a colleague of mine (who I'm friends with) said to another colleague that he has an interview coming. He works full-time so I knew that this means he could be leaving, so I asked him if he's leaving. But I worried in case he might have thought I was being nosy, but then I thought that if I was planning on leaving and announced to someone that I had an interview somewhere else, he would most definitely ask me the same question "so you're leaving then?" So I then thought it was OK.

Sometimes though, I have gained enough courage to ask someone a personal question, only to wish I hadn't because they reacted with a "sshh!" even though there were no obvious hint that it was a secret. I was just asking because they'd already told me about it before but wasn't undated so I just thought that asking would make me look interested in them, as if I didn't ask they might think that I don't care and then I feel that is what deters friendships.

It's only little things like this that I find awkward. Otherwise my social skills aren't that bad. I'm just not the type to ask too many questions.

England can be tougher than what I'm used to, but if you can remember what they were planning to do, you can ask how it went, from watching sports, a knitting project, a birthday party or whatever. This would not work with one group I used to know who would come in on Monday declaring it a great weekend because they couldn't remember a thing about it.

I recommend getting a copy of Dale Carnegie’s Book “How to Win Friends and Influence People”.
One thing that works is to try to find a way to ask something about a trait you admire about the person - an area where you feel this person excels yourself and ask them about that.
Is the person wearing clothing with a logo of a sports team? Ask them about the team. “Go Bears” (or other team name) is often good for a smile and a good ice breaker. Ask open ended questions about broad subjects like weather or “how do you know (name of host)” can work at group gatherings.

I feel that you can ask any question if you are not going to judge, and willing to hear the actual answers. Don't ask about anything you don't want to know, say like STD. I'd try to stick to general, pleasant topics like cooking, crafts or movies. I've known enough people who like to complain, and I really don't want to be their therapist. I seem to have the unfortunately talent to make people open up and pour their souls out. I never intended to know them that much.

Yes it's an interesting book and without reading it I might never have realised that so many people want to be flattered. But I soon worked out that I couldn't handle the boredom of listening to somebody talking about their own interests when they had little or no connection to mine, and the whole thing felt like a sellout, pretending to be interested just to butter people up. In fact Carnegie was a salesman who (in his book) applied his psychological salesmanship methods to the art of winning friends, and as salesmanship is mostly a con trick, so are Carnegie's social tips. I'm sure they're quite powerful for making short-term gains, but for me friendship is a deeper and more long-lasting thing that will eventually collapse if it's built on lies. Even if I could stand allowing the entire conversation to be about them, and retain the random things they said to me, I'd not be happy with a friendship that was so one-way.

So instead, I try to look for common interests and a nice reciprocal conversation about those, where nobody is straining to take an interest in stuff they don't really like. It's a rare thing to find such "like minds," and if I used the Carnegie approach then I expect I'd have a lot more contacts who had some goodwill towards me and thought me an interesting person, but it wouldn't be me they liked, it would be the fact that I seemed interested in them and seemed to admire them. There'd be nothing in it for me on the level of friendship, and the constant sublimation of myself to their ideology would wear me down. In theory I could just ditch all but the ones who weren't greedy, the ones who said "but enough of me, what about you?" The trouble is, that doesn't happen very often. People - self included - are depressingly full of themselves, in my experience.

^ It is true that Carnigie worked with sales people. His biography included managing radio talent - which is a bit like sales. I disagree with the idea that Dale Carnegie recommends false flattery. He specifically says that flattery is false, like counterfeit money and that you will get into trouble passing it sooner or later.

If you really think you are better than everyone else at everything else and there is nothing to admire about anyone else you have a problem called narcissism.
Also some people are competitive by nature, so praising someone may seem like “admitting loss” which is intolerable to the competitors.

OP wanted to know how to converse with and take an interest in people. Topics of common interest are a good option for conversation. So are topics of special interest for the other person. I had a co-worker who was a biologist with a phd. He had switched careers to computers layer in life. His hobby was bird watching. He would take trips to observe birds in different parts of the country. I would often ask him about bird watching, which I felt he knew more about than I did. I would ask him about how he photographed them and many other things. I learned a lot about birds and about him.
I could ask him “do any bird watching lately?”. Asking about current events in an are that interests someone if a good way to keep the conversation going.
I had another coworker who had many hobbies - one was Rubic’s Cubes. I am interested in that too. We could talk about cubes and I learned a few things I didn’t know from him. He also had a hobby of building things, he liked working with wood and electronics. He built a electronic videogame/pinball machine full arcade size. It had a flat screen tv/monitor as a top and buttons to serve as bumpers, and a second screen to display scores. It used a computer to emulate the arcade hardware and ran copies of original roms. He also built a box with mirrors and leds to create an infinite hallway. I learned about things by asking questions like “what do you like to do when you aren’t working?” Or “do anything interesting over the weekend?”

Another book to look at is Seven Habits of Highly Effective People.
It says “seek first to understand, then to be understood”. It can fit well with Dale Carnegie’s book.