3 Crucial Questions to Ask Your Teen Who Wants to Date

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Ask your teenager these questions before they start dating.

My daughter decided not to kiss dating goodbye—and I was OK with that.

In 1997, Joshua Harris released I Kissed Dating Goodbye. Hundreds of thousands of Evangelicals read this book. It eventually sold more than a million copies and the language of “courtship” ensconced itself into the 1990s’ Christian speak. I was a youth pastor at the time and I too read Harris’ book. Like so many parents, Harris’ thinking fit nicely with my view of the world. Namely that there was a breed of human—the teenage boy—who would soon be out to get my little Jacquelyn. And furthermore, there was going to be no way I would let this happen.

For many Christian parents—particularly men—this is a familiar narrative. Like sentries on duty in wartime, we think it is the job of parents to keep boys away from our daughters. While well-intentioned, many Christians (including myself) used this book as further evidence that our daughters should offer an emphatic “NO!” to anything that looked like dating. In my family’s case, I pushed a belief on my daughter that she did not share. What I tried to do was control my daughter instead of talking with her. Rather than sowing understanding, I was trying to cultivate compliance. This approach backfired. It merely pushed my daughter and her dating life underground

In my 20-plus years as a school teacher, I’ve realized there are two approaches to our teenage daughters and their dating lives. The first is the, “I have a shotgun and am not afraid to use it” approach. While we joke about this approach, many Christian parents view dating this way. We really don’t want our daughters involved with boys and are willing to scare boys into not dating them. The second approach is a laissez-faire approach. This is the “Don’t get pregnant or an STD” approach. For the non-Christian world, this is all too common. As long as a girl doesn’t get pregnant or an STD, then pretty much everything is permissible. Between these poles, I believe there is land in the middle that parents should stand on.


This land is one where parents teach rather than tell. It is a land where there is discussion and not directives. It is a place where compromise takes the place of compliance. In short, parents together with their daughters build a mutual understanding of what dating will look like. This is a very hard thing to do for many families. The fear that our daughters will make monumental mistakes clouds our thinking and judgment. As a result, we try to get our daughters to bend to our wishes.

There are three key questions that should be at the heart of any discussion around dating:

  1. What do you hope to get out of dating?
  2. What are boundaries you want to observe as you date?
  3. How will you date so that it won’t impact your future happiness?

Parents should talk these questions out with our daughters. Even if we aren’t 100 percent satisfied with the answers to these questions, they are the basis from which parents can instruct and discuss what dating might look like.

Seven years after botching the job with my oldest daughter, I was given another chance with my younger daughter. This time around I was more open to the idea of my daughter dating. Was I happy about it? Not really. My desire to protect my daughter was still strong. But instead of coercing her into my way of thinking, I was focused on allowing my daughter to be who she was. I let her explore the world of dating and relationships with input from her mother and me. I did not force her to go it alone because I insisted she kiss dating goodbye—even when she didn’t want to. I let my youngest daughter decide if she wanted to kiss dating goodbye, and I’m OK with that. {eoa}


Daniel Anderson is a former college all-American basketball player, an expert educator, and a father of two grown daughters and a son. As a veteran high school teacher in the public school system, Daniel was troubled by how his students approached dating and relationships. He and his daughter, Jacquelyn Anderson—a 20-something and also a high school teacher—decided to address this need by equipping parents with The 10 Myths of Teen Dating, their first book together. Daniel and Jacquelyn both make their home in Portland, Oregon. Find out more about Daniel and Jacquelyn at thetenmythsofteendating.com.

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