As anyone who has experienced loneliness can tell you, feeling lonely is not the same as being alone. At the same time, it is possible to have many people in your life, while still feeling lonely.

Sometimes, the circumstances that lead to our loneliness are out of our control. Some of us have lost our spouses or gone through a divorce. Others have children who are building their own lives in another part of the world.

On the other hand, many of us feel like we have plenty of acquaintances and very few “true friends.” In talking with other men and women my age, I have come to the conclusion that part of the problem here is the cultural and technological context in which we live. Let me explain.

Feeling Lonely with Hundreds of “Friends”

If you are like most people, you probably have 100+ friends on Facebook. You may even send the occasional short message to ask how your friends are doing. But, do you ever ask questions that dig below the surface?

Maybe there is something about social media that encourages us to keep things on a surface level. Whatever the reason, I am convinced that true friendship requires us to ask the “tough questions.” If we want to be happy, we cannot allow ourselves to be satisfied with knowing where our friends are and what they are doing. We must know what is in their minds and feel what is in their hearts.

The next time that you have an opportunity to go out to coffee with a friend, why not take a chance and ask them a truly difficult question? The next time you have a Skype call with your kids, instead of asking them “what’s new,” why not get their feedback on a dilemma that you are facing?

Let’s refuse to let our relationships turn into blank canvases. Let’s paint them with bold statements and thought provoking questions.

Let’s Take a Chance with Intimacy and Ask the Tough Questions!

What is the most interesting question that you have ever been asked? Do you agree that asking “tough” questions is essential to building and maintaining friendships? Please join the conversation below.