3 Questions to Ask Your Son Before He Starts Dating

A Father's Stance on Middle School Dating

A couple of 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:*

(Dear reader, you may be advanced in years and wisdom beyond me and have perhaps already traveled this path. Your advice and/or supportive anecdotes are more than welcome in the comments!)

Question 1:

What would you do if your girlfriend told you she was moving to Ecuador?

The first girl I ever asked out was Ariel Demas. We were in middle school, though I couldn’t tell you if it was 7th or 8th grade. My girl radar was in full effect, and I thought I was ready to take the leap. Ariel was cute, kind, and laughed at most of my jokes, so I sought her out after English class one day and abruptly asked her, “Do you want to go out with me?”

She said, “Yes,” and that was it. We went our separate ways, picking up books from our lockers and heading to our respective classes. Ariel and I “dated” for the rest of the school year, though I’m not really sure what that meant. I don’t think we ever hung out outside of school. I still played soccer and ultimate frisbee with my friends during recess. I don’t recall ever holding her hand. We certainly never kissed. The apex of our relationship would have been slow-dancing to Boyz II Men songs at a school dance. 

At the end of the school year, Ariel informed me that her family planned to move to Ecuador for a year. At 14-years-old, a year might as well have been a lifetime, and Ecuador might as well have been as far away as Peru. Though we didn’t actually “break up,” we silently, though mutually, assumed our relationship was over.

A few days before Ariel was scheduled to leave, my friend Josh, who was far more suave and socially aware than I was, urged me to get Ariel a parting gift. There were two stores he and I frequented together in those days: the comic book store and the record store. I imagined the latest episode of Spider-Man wouldn’t impress her, so we took to browsing the aisles of cassettes at Record City. After all, music has a profound way of speaking to the heart. I carefully selected a single off the New Release rack (I didn’t have much allowance back then, and I certainly didn’t want to spend money on a full-length album for someone who was walking out of my life), and we went on our way. 

Josh and I stopped by Ariel’s house later that day and I presented her with the token of my adolescent affection. She seemed grateful for the gesture, but wholly unimpressed with my selection. Apparently Metallica’s new single, The Unforgiven wasn’t the most natural choice as a going away gift for young, star-crossed lovers. And just like that our relationship was over. 

Idiotic gift-giving is the first sign that a middle school boy is not ready for a serious relationship. Though unlikely to break through to a stubborn or strong-willed teenager, this line of questioning could serve as a deterrent to early dating. At the very least it will prepare him for the characteristic of healthy relationships known as thoughtfulness.

Question #2:

How often do you want to celebrate anniversaries?

Notice the question is not, “How often is it appropriate to celebrate anniversaries?” Appropriateness has nothing to do with it. Your son could answer that question correctly (answer: at 6 months, 1 Year, and only annually following that) and still be totally unprepared for what awaits him.

I scanned Evan’s text messages a few weeks ago** and found a humorous conversation with his gal pal:

It is important to walk through this timeline with your son, should he desire to start dating. 10 days prior to the 1-month anniversary (not a thing), a middle school girl can and will start reminding him that their 1-month anniversary (nope, not a thing) is coming. This means that only 20 days after initially becoming a "couple" he will start receiving pressure to celebrate the first in what will undoubtedly be a long-list of meaningless celebrations and affirmations. 

As the (fake) Big Day approached, other text messages streamed in, asking my son what he would be getting her. She made it abundantly clear that she had been thinking about a gift for a long time, and he was expected to be thoughtful and generous as well. 

The night before the 30-day mark, Evan and I were driving home from soccer practice when he startled himself. “Shoot! I almost forgot I need to make cookies tonight!”

“What do you need cookies for?” I asked innocently. 

“My girlfriend. But she doesn’t know I’m making them.”

“Ah. Is it your ‘big day,’ then?” 

“Mmm hmm.”

We arrived home, Evan showered, and then, as he does most every night, he jumped on the Xbox. Just like that, the anniversary had been forgotten. As fortune would have it, my wife had already baked/burned a batch of peanut butter cookies that evening. When Evan was walking out the door the next morning, Erica smiled knowingly and handed him a baggie with a few imperfect cookies. “You don’t want to forget these,” she said with a smile. She had even placed the treats inside a cute little goodie bag she managed to scrounge up for him. (Granted, it was an old Halloween goodie bag, but it's your mom's thought that counts, right?)

At dinner that night, we asked Evan if his girlfriend appreciate the gesture. “I guess,” he responded. 

"Did she like the cookies?"

"I think so. I don't know. She didn't really say anything about it."  This is a clear sign that she most certainly did not like the cookies. But I didn't tell Evan. He'll figure that out another day.

“What did she get you?” we wondered.

“It’s, like, this coin bank thing. Which is annoying because it means that I have to empty my other coin bank just to put all those coins into the one she got me.”

“I can see that,” I chuckled. “But it sounds like she thought about that gift for a while.”

“Yeah,” he replied. And then, “I hope we don’t have to do this at two months.”

And there it is.

Parents, let your sons know early that relationships take work. A LOT of work. It can’t hurt to suggest to our boys that they will never be prepared for the onslaught of expectations that will suddenly be placed on them if they decide to date in middle school. Little things are ALWAYS big things, and there are A TON of little things! Burnt peanut butter cookies are only going to placate a girl for so long!

Question #3:

Is the girl you want to date going to help you become better or worse than the person you want to be?

This is one of the most important questions we can ask our sons. In fact, feel free to ignore the other two if you’d like. This question is the one that can give birth to the most meaningful conversations. See, every child has a vision of the kind of person they’d like to be as they grow up. It may not always be a crystal clear picture - it may not contain many specifics at all - but every kid has an idea of what it looks like to be a grown up. Certainly they have clarity about the kind of person they don’t want to be. 

No child enters middle school hoping to start smoking or become a teenage parent. They don’t aspire to be addicts or dropouts. They have hopes and dreams of becoming something - someone who matters. Once they reach middle school, the friends our kids choose become the biggest influencers in their decision-making. Intellectually, I have known this for a long time, but it hit me like a pillowcase full of doorknobs when I realized he was now dating a girl. More than anything else, at least for the next five or six years, friends will determine the direction of my son's life.

choose wisely.png

Some of the incoming messages I had been intercepting on his phone were cause for concern in this regard, so I knew it was time to revisit this topic of conversation. I reminded him that he will likely choose similar behaviors to the people he chooses to hang out with, which means choosing friends wisely is one of the most important things he can do. This is just as true, if not more so, when choosing to date a girl. If the girl shares his values, beliefs, and has similar aspirations for her life, the relationship has the potential to be mutually beneficial, encouraging, and God-honoring. But if he chooses to date a girl whose worldview and whose desires are a far cry from where he wants to be, it’s more likely than not that he will be pulled in a direction he does not want to go.

This was probably the most meaningful conversation I’ve had with my son in a while. He was able to recognize and verbalize (which can be a miracle when dealing with a 14-year-old boy) the fact that his girlfriend is moving too quickly with some things and that she probably isn’t wanting the same things for her life that he wants right now. That's a huge red flag for me as a parent. 

One of the most important things I can do for my son is to help him choose his friends wisely. Even his girlfriends. Especially his girlfriends.

Not wanting to force ultimatums on Evan about who he can or can’t date, this simple question allowed us to have a productive conversation about recognizing the need for healthy relationships all around. He walked away feeling supported by his father and challenged to make mature decisions about the friendships in which he chooses to invest. There was no immediate reaction to our conversation. He didn't go out and break up with this girl the next day. But I knew he was thinking about it - thinking about what he really wanted and the direction things were going for him the more time he spent with her. 

It's hard to say exactly, but from my vantage point it appeared as if he slowly began pulling away from the relationship. Text messages decreased in both frequency and length. He stopped FaceTime-ing her while playing on the Xbox. I can't be sure, but from all appearances it seemed as Evan was simply trying to ease out of things. And then, even as I was writing this post, she sent the message we had secretly been hoping for: "I think we should break up."

And there was much rejoicing.

Seriously. My wife and I feel like Evan dodged a bullet. We had concerns about where this girl was trying to lead him, and Evan himself acknowledged the same pressure. The break-up occurred right before dinner, and Evan was in an unusually great mood for the rest of the evening. He seemed lighter, relieved. 

Today is not the day, but at some point I'll have to teach the kid that it's not best-practice to simply start ignoring your girlfriend, even if you want out of the deal. He'll need to learn that break-ups are best handled honestly and directly. Or by gifting her a Metallica single. 

What about you? How do you handle parenting your kids through dating in Middle School or High School?

* Girls and boys are different. I'm sure the conversations I have with my daughter in the not-too-distant future will have their own distinct angle and tone. 

**If you don’t know this already, reading your kids’ phone messages is completely appropriate and, I would argue, one of the most important tools in your parenting arsenal. It most definitely does not constitute a breach of privacy. It’s your kid. He/She is a child. They don’t get that kind of privacy or secrecy yet.

Dan Jackson

Dan is a pastor, writer, speaker. He is the host of the Ordinary Faith Podcast and currently serves as a Campus Pastor for Southland Christian Church in Georgetown, KY.