I wonder if there is anything that can be done for my "problem" or if I should just learn to accept things as they are. I'm a rapidly rising executive at a technology company (we have "real" products and "real" profits so the dot-com burnout hasn't affected us at all). Never married, no children (no desire to get married or to have any kids), no girlfriend, no friends. That's my problem. I am very lonely a lot of the time, especially when I'm not working.
I can't bring myself to trust people enough to become friends with them. I can do OK at business receptions because we talk about business, but I am very uncomfortable in even casual social situations. When someone asks even a simple question like, "Where do you live?" I figure they are really trying to guess how much money I have. I especially don't trust women, which is why I haven't ever had a girlfriend. After I've gone out with someone a few times and they start asking "personal" questions, my guard goes up and I stop seeing them. As for male friends, I don't like sports or cars or sex, so I don't have much in common to talk about with them and thus don't "hang out" with guys. I had a good relationship with my parents when I was growing up, and my two brothers and I used to spend a lot of time together. But now one lives in Europe, one in Asia and I'm in the US so we don't see each other very much. Because of time changes, it's not even easy to talk on the phone very often.
Is there some way to learn not to feel lonely? It doesn't bother me all the time, but sometimes it seems very empty in my house. When I see couples together, or a group of men talking together in a restaurant, I wonder how they make friends and why they can share information about themselves but I can't. Is it unusual to be so distrusting, or do most people just cover it up better than I do? Why do people always want to ask such personal questions about others? I mean, when I meet someone it wouldn't occur to me to ask some of the questions people ask of me, like "Where do you live" and "Where do you go on vacation?" Is it normal to feel like everyone is prying into my personal business? This is just an example, but I don't care where my secretary lives, for instance, or what she did on the weekend. Why do relative strangers feel like they can just ask anything of anyone?
You speak of an extreme loneliness yet preventing you from making friends is an extreme distrust of others. An inability to trust others generally stems from some past experience where someone in whom we placed trust badly let us down. However, if this should be the case, to never trust another because one person has betrayed our trust is giving too much power to that person. There will always be those who abuse our trust. Con men and women are very plausible. They need to be in order to take our possessions away from us. Yet there will always be people who are fully trustworthy. What we can do is to trust a little. When the other person has shown that s/he can respect that trust, then we can trust a little bit more, and so on.
Another instance leading to difficulty in trusting others is perhaps a role model in childhood (a parent or some significant authority figure). In that case, one would learn vicariously about the dangers of trusting. There certainly are dangers in trusting strangers. But not to trust brings about the loneliness that you are experiencing. In other words, life itself is a risk. We can lock ourselves in a box for a lifetime and we will never get hurt and we never learn about love and friendship. Or we can boldly go forward risking all those emotional knocks and bruises that we all know about.
Further, you mention how indelicate and insensitive others can be in terms of personal questioning. It is true. You are right. However, it is also right to say that people are human. Albert Ellis, a renowned psychologist wrote that people are fallible, but they are also worthwhile. So expecting the world and all the people in it to be perfect is unrealistic and one is heading for an emotional fall if one pursues such demands. Cognitive therapists call such demands: "Musts and Shoulds". Rather than demanding that others do the right thing, it is better to say: "I would prefer it if s/he were more polite". Then we are being realistic in our expectations of the world.
Having said that, it is frustrating to meet people who are extremely insensitive. One thing we can do is to be assertive and respond positively to some remark such as "where do you live?" with perhaps: "Is it important?" or "Oh, around and about". You are allowed to say No in other words. Or sidestep a question that you feel is intrusive. If done politely, no harm should be done. However, understanding why such things occur may help. People often are shy. While I am sure that there are those who just feel they have a right to know all your business (those who have not learned about barriers and personal space), there are those who simply do not know what to talk about with strangers, and so ask questions. For a shy person, asking questions of the other is a good way to get the other talking. Since people usually love to talk about themselves, this is a boon for the shy person.
The fact that you see behind such questions, however, something sinister is unusual. But since you cannot know for certain that someone who asks where you live is either going to rob you, or wanting to marry you for your money, it would be helpful for you to cultivate a tolerance for those with many questions. Just because you would not ask such sensitive questions does not mean that others see the same sensitivity about where one lives. The groups of people you see together, for instance, and wonder how they made friends. One of the "hows" is that they began a friendship perhaps with trivia such as where one lives. When you do see groups of people laughing and chatting, you might remind yourself that it is your choice not to trust people, and with that does come a certain loneliness. Those other people you see in groups have chosen to be with others to avoid loneliness. But they have nothing more than you do other than the need to be with others.
I would like to move now to some areas where you too might start to make friends if that is your wish. Often our interests and hobbies provide meeting places. This assumes that you do have an interest outside home and work. I really believe that we need such a balanced life in order to be psychologically healthy. Having an interest outside home and work also provides more stability in times of crisis with home and work. In terms of an interest or hobby, 2000 years ago, in Egypt, some papers were found in a stone jar and turned out to be written, archeologists believe, by a religious sect. Well religious or not, the following is so profound that I thought I would like to share it with you. "If you bring forth what is within you, what is within you will save you. If you do not bring forth what is within you, what is within you will destroy you."
So, Bill, I hope you will take heart. It is never too late to start widening your circle of acquaintances and friends. You might find an interest in art, ceramics, learning a musical instrument and so on. There are dozens of interests to choose from. Or you might prefer a walking or cycling club. You notice I am speaking of group activities where inevitably one must interact with others. Others might well, of course, ask personal questions. Be patient and tolerant and do not assume an ulterior motive, other than: "I want to talk to someone, and possibly make a friend of you". It is called "small talk". It is pretty meaningless but a means to making friends.
Bill, one other thing might be that your self-esteem is low. Lack of trust of others is an indication of this. Try to raise your self-value. When you start to think highly of yourself, others will too. When you think little of yourself, there is a tendency for others to pick up on this and think as you do. There is a good book on the subject of self-esteem called Six Pillars of Self Esteem by Nath Branden. It is about having aims and goals and interests, and feeling good about achieving. This does not necessarily have to be achieving at work but can simply be in life generally. Once it starts, there tends to be a flow on effect. Finally, a good way to fill one's time and an environment where one can make friends is by giving. Choose some charity work for a few hours a week. Put some effort into it and it will be returned threefold.
Bill, if you work on not being suspicious of other people and start to be proactive in your social life, accepting that there will be some disappointments along the way, but many rewarding moments also, I think you will find good people like yourself to be with, and be a much happier person for it.
Many best wishes.