Middle School: An Open Letter to My Son in this Time of Transition


Since my sensitive son entered 5th grade two years ago, his middle school experiences cause me to remember this awkward time of life in vivid, unwelcome detail. As I witness his struggles helplessly from the sidelines, my daily advice to him involves some version of “just survive it.”

Middle school, cross country
Watching your middle school race from the sidelines…

In an effort to offer more perspective, comfort, and loving support, I wrote this open letter to my son on how to make it through the awkward, difficult years of middle school.

Dear Son,

How did twelve years pass by so quickly? Here you stand now – not quite a boy, not yet a man. When pregnant with you, I received parenting advice from a dad that resonates with me today. “Transitions are hard,” he told me. At the time, he meant infant and toddler transitions, changes like starting solid foods, walking, potty training, and the countless other basic milestones of human development. At the time, we both failed to register the monumental transition from child to teenager that awaited us, the longer-than-you-might-expect middle school years.

The paradoxes during this time seem endless. Part of me wishes you could stay a little boy. Part of me can’t wait to meet the man you will become. All of me wants to make this uncomfortable time of change and growth easier for you. None of these things seem possible.

middle school, still little
You still look 5 years old to me in this photo…

All I can say, kid, is when you feel alone – and you will during this time – I’m here for you, always and forever. I stand by your side, even when I’m physically not there. Your mother loves you, no matter what, and, perhaps more importantly, likes you for exactly who you are.

I know you think I’m making this transition harder for you.

middle school, obstacle course
Middle school is already an obstacle course…

Unlike your friends, you’ve never played Fortnite for hours (or days) on end. We slowly scratch the surface of the Marvel universe of movies. You watch only under our supervision so we can discuss any disturbing images or subjects. I hear you when you tell me you can’t converse effectively with the other boys at school who have watched them all, multiple times. We completely missed the boat on the Fortnite phase. I know I’m cramping your style, but in this arena, I just refuse to change my parenting approach based on peer pressure. Once seen, some things cannot be unseen.

Middle school, my darling boy, is your last chance to hang on to the vestiges of childhood.

I want you to grow up, just not too fast. Believe it or not, some of your Marvel- and Fortnite-crazed friends might actually feel jealous of you and your “unreasonable” mother. If they spend all of their time in their room glued to a TV, a handheld device, or a computer screen, they might actually crave the kind of walks, talks, meals, board games, book discussions, and general quality time that you and I enjoy. Someday, you might believe me when I float this idea.

According to your accounts, kids start “dating” in middle school.

These days, I’m not quite sure exactly what that term means for 11-, 12-, and 13-year-olds without independent transportation. In my middle school days, we engaged in “going together” with the opposite sex, which meant holding hands as we circled the school hallways before class in the mornings, passing notes, sitting together on the bus, hanging out during field trips, and sometimes talking on the phone at night. Maybe it’s the same for you? I’m not quite naïve enough to think that’s the extent of it in the smartphone age.

You asked why I disabled the camera on your iPhone.

Pictures on the Internet last forever. Snapchat allows screenshots. Middle school boys and girls live day-to-day at the mercy of their newly emerging hormones and lack of prefrontal lobe development to comprehend consequences. End of discussion.

For the first time, you asked a girl out this year.

While she said “No,” I could not feel prouder of you. I honor and applaud your courage, your bravery, and your graceful handling of your first rejection in the dating realm. You treated her with respect and kindness, and when she did not return your affection, you licked your wounds and moved on. Unfortunately, she continued to pursue your attention, in spite of her lack of interest in you romantically. When she failed to secure your continued affection, she turned on you and teased you mercilessly, recruiting others in her bid to get attention from you in negative and less than constructive ways. I watched you hurt through this ordeal, but you held up great.

Neither of us derived much comfort from my words of wisdom on this subject: middle school girls can be mean.

Your old mom, who wants nothing more than to protect you from these harsh realities, was once herself a mean middle school girl. May I take this occasion to apologize profusely to the mothers of all the middle school boys I mistreated? In true karmic fashion, my heart now aches both for my own son and for what I put your sons through.

Does it help to know why middle school girls are mean?

If memory serves correctly, insecurity plays a major part. Middle school girls want boys to like them but don’t feel ready to deal with their affection when it comes. They worry that if a boy gets to know them too well he won’t like them after all. In this sense, it’s easier for them to hang out in a protective “pack” of girls (as you so aptly call it), rather than intermingle romantically with boys. Additionally, middle school girls share very few common interests with middle school boys. While you love to talk in detail about Warhammer, Dungeons & Dragons, and other boyish subjects, girls your age enjoy wildly different interests and topics of conversation.  

middle school, boba fett
Yeah, most middle school girls can’t relate to this…

Middle school girls also haven’t gotten used to their new bodies yet.

In some cruel joke by the universe, most girls emerge from middle school fully grown physically and a long way down the path of puberty. (Your old mom hasn’t grown an inch since the age of 12.) At the same time, middle school boys vary widely in their progress towards a manly physique. Some shoot up in height, while others remain boyishly short with peach fuzz mustaches and cracking voices. Middle school girls suffer the frustration of having to wait for boys to grow up (literally) and catch up to them in physical maturity. As a result, their affection quickly shifts to older, more mature high school boys. (Ouch!)

Middle school, dancing
You will catch up to that much taller middle school girl next to you…

While I know your feelings often get hurt, remember you are a smart, funny, kind, and good-looking boy. Be patient, and romantic attention from the right girls will come.  

On that note, I offer you these final five final pieces of advice on surviving your middle school years:  

  1. Be kind – first and foremost to yourself and second to others. Walk away from the ones who take advantage of your kindness without returning it. I give you permission.
  2. Focus on schoolwork. They call it middle school for a reason. Learning lasts; relationships often do not. Build the academic blocks of your future. Don’t worry about kids calling you a nerd or not being able to relate to the Marvel-heads and Fornite maniacs. You know how much you love John Green, the author of The Fault in Our Stars? He shrewdly asks, “Why is being a nerd bad? Saying I notice you’re a nerd is like saying, ‘Hey, I notice that you’d rather be intelligent than be stupid, that you’d rather be thoughtful than be vapid, that you believe that there are things that matter more than the arrest record of Lindsey Lohan.’” Be that guy.  
  3. Smell good. In other words, draw attention to your physical self for good reasons rather than bad smells. How do you achieve this goal? It’s easy. Bathe daily (with soap). Wash your hair daily (with shampoo). Wear deodorant daily. Brush your teeth (and tongue) twice a day. Drink a lot of water. (Believe it or not, it impacts how your breath smells.)
  4. Respect and consent. When engaged with the opposite sex, live by these two concepts. Respect girls and their boundaries. When you do find a girl smart enough to return your affections, ask first and get her consent before things get physical. Come to me when you need condoms. As a boy/man, you are responsible for this form of birth control and sexually transmitted infection/disease prevention – every single time you have sex.
  5. Stay alive. I’m not kidding. Suicide is the second leading cause of death in your age group (10-14) in the United States. I get it. Middle school is hard, but how unthinkably awful would it be to end your life there?

Survive middle school so you can enjoy the rest of your life. I promise it only gets better.

Middle school, cross country
Keep running. You’ve got this.

Thanks for reading. I love you.




  1. This brought me to tears and my son is only 3. I hope that I remember this post when he’s in the 5th grade. It’s gorgeous and poignant.


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