Making Space for Awkward Conversations with Teens

“And these words which I command you today shall be in your heart. You shall teach them diligently to your children, and shall talk of them when you sit in your house, when you walk by the way, when you lie down, and when you rise up.” (Deuteronomy 6:6–7, NKJV)

In an age where children do not follow their parents to the workplace on a daily basis, it is incumbent upon us fathers to make time for fulfilling the commandment to teach our children diligently.

I have a son; he is fifteen … and the world is dark, and the stakes are high. One day, he will have to make his way in the world, setting his own standards and restraining himself rather than living under his mother’s and father’s rules.

His path toward wise decision-making now and in the future is shaped by his thought life. Sins of the mind are secret sins, and they have an insidious way of robbing men of their sons and their daughters. We take great precautions to protect our homes from robbers and thieves by having locks and sometimes security systems as well, but what of those who would steal the hearts and minds of our children? How can we combat the enemy and have greater influence on a child’s thought life?

My wife is a wonderful partner in the battle for my son’s character. She has had some great ideas, and I highly value her input. We implemented one of these ideas several years ago when she suggested that we pick a routine time for me to have “awkward conversations” with my son. These would be conversations that, Lord willing, would help proactively shape his thinking in important areas.

Without a specific strategy, I might have delayed indefinitely for the “right” time, and might have had to deal with some of these topics reactively, which is not ideal. We began sometime in his seventh-grade year.

The topics that my son and I have discussed range broadly, as you will see on the list below. Some may sound shocking, but my wife and I believe that starting these tough conversations allows the parent to be a foundational source of information on these sensitive topics, a concept our pastor has taught.

Planning the Time

I work long hours in a corporate setting and don’t always feel like talking, so my wife and I drafted a list of topics for my son and me to discuss. We used the list-sharing app “To Do” so the plan would be handy and my wife could easily have input.

• Aggressive girls
• STDs
• Boy Scout scandal
• The husband-wife relationship
• Being a friend to younger siblings, not a ruler
• Circumcision
• The Catholic abuse scandal
• A multitude of school-related interactions
• Homosexuality
• Pornography

Understanding the Time

We chose a time that would be consistent and adequate, but not open-ended, so that any awkwardness would have a defined end point. The end point was also a time when our son would naturally move on to another activity, a strategy to avoid him dwelling on topics too long (which could happen, for instance, at bedtime).

For our purposes, that time has been the one day each week that I pick him up from school. The ride home gives us a twenty-minute conversation window, and when we arrive he has various free-time activities to switch his focus to.

At some point our sessions developed from “awkward conversations” that I led to an “ask me anything” opportunity that my son felt safe to participate in. I began inviting him to do so, and the consistent time and place has allowed him to plan as well. It surprised me the first time he got into the car and said, “Okay, I have three questions today.”

Not only the timing, but also the setting of our conversations is important. While driving we are able to look at traffic rather than feeling compelled to make eye contact. It allows the conversation to just flow without my son feeling conspicuous. My wife and I credit Dr. Jim Berg for the wisdom of side-by-side (rather than face-to-face) interaction and the lessening of tension that produces.

Also, repetition has been helpful. We have spoken about some topics more than once because they just didn’t click at first. Our pastor likes to say “repetition aids learning,” and that principle applies to these topics.

A Surprise

One day I shared with our pastor that God had allowed my son and me to develop a very strong relationship. He noted that he had seen a maturing in him, and I told him about our weekly interactions. I see those as a key factor in the growth of our relationship. It has developed far beyond my expectations for this time in our lives.

It is amazing how the conversations have become much more two-way with my son asking me for personal insights based on my experiences. That was the true surprise.

Other times when we drive together, we love to listen to audiobooks, and have done so ever since I started taking him to school in the mornings. We have listened to light-hearted books written by Mark Twain or P.G. Wodehouse and weightier material authored by the likes of Charles Dickens. We even “braved” the story of the Endurance together.

We always have a book we are listening to, and he always wants to listen to it. These shared experiences have also helped us bond, and they prompt other conversations. But as much as we enjoy audio books together, we don’t ever listen to one during our ask me anything time. It is reserved for a singular purpose, and we both recognize and value that.

Currently, my role as father/mentor/coach is in full swing, but the transition to father/friend is in sight and approaches ever closer with each passing year. I pray that the seeds planted today will pay off in the coming years as my son makes choices and as our relationship continues to develop.

The saying goes “Little people have little problems, but big people have big problems.” Just because he grows up doesn’t mean he won’t need a father. I also have another son; he is 12 … and the world is dark, and the stakes are high. I am seeking a time to implement conversations with him as well.