3 Questions to Ask Your Son Before He Starts Dating

3 Questions to Ask Your Son Before He Starts Dating

A couple months ago, my wife and I were shocked to discover that, unbeknownst to us, our son had his first girlfriend. An eighth-grader, he had previously shown no interest whatsoever in dating. He talks about soccer and Destiny 2 and camping trips, but never girls. Yet sure enough, we scrolled through his text messages and discovered a thread we were not prepared for: an unknown number asked on behalf of a girl who sits next to him in band class what he would say if the girl who plays trumpet in the fifth chair asked him out.

He said, “Sure.”

This is how middle school relationship start. In fact, it’s apparently how they are maintained as well. Evan’s iMessage stream is a steady dose of mutual friends texting as third parties to intervene:

  • “Are you mad at her?”
  • “You should call her.”
  • “She wants to know why you didn’t call her.”
  • “She wants you to bring her some chocolate.”

As a father, I had hoped to hold my kids off from dating until they were well into their high school career, at the earliest. Middle school dating is silly and largely pointless. Nevertheless, I also recognize it as a coming-of-age ritual. He’ll learn, he’ll grow, and hopefully he won’t make too many bone-headed mistakes along the way. Most importantly, I hope he doesn't compromise himself or anyone else during this process of discovery.

While I once thought I would have hard-and-fast rules for my kids about dating, I’m now more interested in having conversations with them. At this point, I figure I'll be more effective helping them navigate relationships and situations rather than trying to prevent them altogether. This is new territory for my wife and I as parents. In an effort to help myself cope with the fact that I know nothing about parenting teenagers - and perhaps to help you if you find yourself on the same journey - I've decided to document some thoughts. Here are three important questions you can ask your middle-school son to help him know if he’s ready to start dating: