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Know someone navigating a new parenting phase this fall? Share this list (consider pairing it with a coffee gift card!) to help family and friends grow together as their kids grow up. And join us again soon for more great conversation starters from our Tell me more blog post series.
Last summer as my oldest child approached her first year of middle school, I was having all the feels, as they say. The transition from elementary to middle school was tough for me to wrap my mind—and heart—around. And I don’t think I’m alone in that experience.
The days of wiggling loose teeth, playing pretend, and welcoming me home from work by running towards me full-throttle to wrap me in a hug are giving way to assertions of “Mom, I know.” And requests like, “Please don’t get out of the car at school, Dad.”
And the questions. So many questions. Questions from my middle schooler. Questions I have about my middle schooler. Cell phones, parties, walking around town without an adult … Is that even legal?
Worrying about the first days of middle school may seem quaint if we look back on this transition from the daunting world of high school or college “firsts.” But as my oldest entered middle school, I was not comparing it to first driver’s license or first days of college. Instead, the milestones in our parental awareness were things like first steps and first day of Kindergarten.
Even if it’s not your first time having a middle schooler in your life, each year and each child brings their own unique challenges. Homework solutions that fit one kid may not fit another. Technology changes so fast that we have to keep “updating our operating system” as parents desperately trying to navigate it.
But one of my favorite things about my kids getting older is that our conversations get richer and more thoughtful.
Tweet: "One of my favorite things about my kids getting older is that our conversations get richer and more thoughtful."
Yet if you’re like me, thoughtful conversations can be a challenge in the midst of daily logistics about carpooling and homework. Start the new school year off strong by committing to one meaningful conversation a week with the middle school student in your life. Here are eight ideas you can use as jumping-off points.
1. Tell me about something that you think is amazing.
One of my favorite things about the past few years has been the new book series, creative apps, music, and random facts that I’ve learned about from my kids. Expanded media intake may harbor challenges as we navigate PG to PG-13, but one of the great things about my kids getting older is seeing good through their eyes. My world expands as their world does. I hear new stories of loyalty or bravery. I laugh at new memes. I learn about history from random YouTube videos.
These new discoveries don’t have to be limited to media: maybe it’s a school club, a new sport, or even a scientific fact. As they grow in independence, asking them what they’re excited about right now can be a great way to learn more about your changing middle schooler.
2. What family rules do you want to discuss?
Whether it’s chores, technology limits, bedtimes, family expectations, or dating—family boundaries might become a touchy topic between you and your middle schooler. If a conflict seems to be recurring between you and your child around a family rule, set a time to talk about it (ideally not in the heat of the moment). This can give you a fuller picture of where your child is coming from. “I want to stay up later” may turn out to be more about having the same bedtime as a younger sibling, or not having any free time after a busy day of homework.
These are challenges you can work creatively together to find solutions for, rather than just insisting (rightly) that sleep is important for your growing adolescent. Opening family rules up to discussion doesn’t mean you give away the right to be the parent, but it can give you fresh insight into what is important to your child.
3. Do you need a hug?
For some kids in this phase, a lot of physical contact is natural, while others are happier with far less. Either way, physical interactions between parent and child will change as our kids grow. While it’s very important to talk about safe touch (if you haven’t had that talk with your middle schoolers, it’s definitely time), we must remember that human touch is one of the most important factors in healthy human development. 
We can help our middle schoolers develop in a healthy way by giving comforting contact in whatever form fits you and your child. While a hug may need to be initiated by you more often than in the past, a well-timed hug can perk up a droopy adolescent and remind them they’re not facing this daunting season alone. And we can help our middle schooler establish their own healthy boundaries around touch by teaching them that it’s okay to talk about it.
4. Have you heard any good jokes lately?
Even though it’s time to get serious about everything from grades to deep questions of belief and meaning, your middle schooler may still really enjoy being a kid. They might sheepishly or boldly request a favorite childhood activity like hide-and-go-seek or a good joke book. They may still play Legos in their room—or with friends. That’s great! Not every conversation has to be serious. These silly moments are just as valuable to your relationship and their development.
5. What is your favorite …?
While we may have known our kids, stepkids, or grandkids for a decade or more at this point in their life, it is important to remember that taste changes. Adolescence is all about change, and so making space to regularly check in with your middle schooler about little or big things can be a meaningful way to learn about their interests.
It can be disheartening when you change but the people you love assume you’re exactly the same. Whether it's a new favorite breakfast food, a new favorite sport, or a new favorite band, I find that learning about these new favorite things—which are often small things—can help acclimate me to the big changes happening in this stage of life.
6. What is God teaching you at school or at church?
One of my favorite things about middle schoolers is watching their faith deepen in complexity. I am so grateful for the adults in our faith community who disciple my kids, and I love to hear my kids tell me in their own words what they are learning. Asking questions during these years can help them start a habit of looking for how God is at work in the world and in their life outside of the walls of the church.
7. What do you need from me as you communicate with your teachers this year?
Whether you have been very involved or relatively hands-off with your child’s education up to this point, middle school is a good time to let them be the ones to communicate with their teachers, while giving them lots of support to do it successfully.
Sometimes I sense palpable frustration and honest confusion from my child about what they should do or say to address a situation with a teacher. If it's something they’ve never done on their own before, I’ll give a lot of guidance. I’ll offer to review an email they type up, or I’ll suggest a few options for times that might be good to approach the teacher with a question. I let them know what I would say if it was me. And if it seems like a particularly difficult situation, I may suggest a few ways the teacher may react, to help them be emotionally prepared for good or bad news. Then I’ll remind them that either way, we will still have a lot of options for how to move forward.
Communicating successfully with teachers (and in the future, professors, bosses, coworkers, or employees) is a skill that will take time to develop. Middle school is a great time to let your child practice while you can still appropriately be a set of training wheels for them to lean on.
8. No matter what, I will always love you.
Our middle schoolers may start to feel like we’re asking a lot of them; like life is asking a lot of them. Finals, travel sports teams, family responsibilities—there are so many new things to learn and navigate in this phase. Asking questions is a great practice, but it’s also essential to regularly remind them that no matter the answers to our questions, and no matter what our kids do, our great God loves them. We love them. Period.
Nine times out of ten this may cue the eye rolling. But you never know which time might be the moment that they really need to hear it.
After all of these conversation starters for us parents, here is one bonus idea for allowing your middle schooler to start the conversation:
(In other words: Allow comfortable silence to be a place they can raise their voice.)
Some of the most meaningful conversations I’ve had with my kids began when they spoke up in a moment of silence. Sometimes they shared a concern. Other times it was reflection. Creating regular spaces for comfortable silence can give a middle schooler a chance to find their voice amid all the daily noise swirling around them.
Shoulder-to-shoulder activities—like a car drive, walking together, or yardwork—can often be a natural fit for this. However, in my case I’ve found the car ride home after a long day of school is not the best time for reflection in our family. My kids are ready for a snack and some quiet. Each of my kids has a different time of day when they are more naturally reflective so, when possible, I try to be available for a long conversation (if needed) in the early mornings for one child and at bedtime for the other. Some personalities need a lot of quiet space to open up, and some may need less.
What’s your favorite conversation starter for a new middle school student and parent? Tweet us @FullerFYI. We love to keep the conversation going!
Click here for the next post in our Tell Me More series.
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