Holding Hands & Breaking Hearts: A Middle School Love Story

Third period.

Ten a.m.

Last week of school.

One of those mornings that has that soft smell of spring, but feels like summer. It’s a good one.

Dennis has a girlfriend. Fine choice, too—Sylvia. I’m assuming if I were thirteen, Sylvia would be the kind of girl I would be too shy to talk to. I would pine away in silence and obscurity. A goth-style yearning. But Dennis took a leap. Fortune and fate tend to favor the bold. Dennis has clearly been shined upon. The two of them are holding hands off and on. He keeps looking back, making sure I don’t catch him. Here’s the thing. I immediately look away every time, I don’t want to catch him, I don’t want him to even know he’s been caught, I refuse to spoil his morning. At thirteen years of age, holding hands with a pretty girl might just feel like the greatest moment of his life up to this point. So really, I’m not going to ruin that. For Dennis, the world is a much better place this morning. The Hot Cheetos he scarfed down for breakfast tasted a little better. He hated math class just a little less. He walks over to me, hoping fortune will reward him just one more time this morning.

“Uhm,” he stammers, with a little hesitation, “Uhm, I really can’t see the movie from my desk. I was wondering if I could sit on the other side of the room when we start to watch.” Now, I’m above ruining his morning but, I’m not above making him squirm a little. I smile.

“You know, I’d respect you way more if you told me that you desperately want to sit next to your girlfriend, instead of this bad angle routine.” I think I see a little sweat start to form on his brow. He leans in.

“Can I please sit next to my girlfriend? Please?” I nod. Go big or go home, right? The best moment of his life up to this point is about to taste just a little bit better.

And so it goes. I have to be honest, watching him lifted my mood a bit. It reminded me of the first hand I ever held that wasn’t about crossing the street. Hard to be in a bad mood reliving one of those.

I’m still smiling when I’m walking with a bunch of kids at the end of the day. I’m herding them to the front of the school. What I see next, literally happens in slow motion, like those moments before an accident. I spot Dennis about to turn a corner, and when he does, he’ll see Sylvia holding hands and smiling with another boy. It’s middle school, a lot can go down in a day. What’s worse is that I can immediately tell from Dennis’ big goofy grin that he is still glowing from the morning. The corner is turned… all the joy leaves his face. I can already feel his heartache and that cold ache that will seep into his gut in about fifteen seconds.

He sees them a split second after I do. His eyes begin to swell.

“Dennis!” I say sternly. He turns to me. At ten in the morning, he was a young man in love. Now, he’s the saddest little boy you’d ever want to see.

“Dennis!” I say again. “Get over here!” He looks confused. “Now!!” He walks over, baffled. I lean in. “Walk with me,” I whisper.

After a few steps, he finally asks, “What did I do?”

“You didn’t do anything. She just doesn’t need to see you cry.” Realizing that he’s not in trouble, his body relaxes, and his total grief from a minute before comes flooding back.

“I shouldn’t cry?” he asks, his eyes too gone to pull back now.

“No, you should cry your eyes out. I just didn’t want you to do it in front of those two. Trust me on this one.”

The tears start falling.

“I’m going to be late for the after school program. I’m going to get in trouble.”

“No. You’re with me and you’re not going back in until you can hold it together.”

“I feel like I’m going to throw up,” he says.

“I know,” I say. “Just keep walking. Deep breaths.” Not much sound. Just the final stages of this first good cry.

Not much sound. Just the final stages of this first good cry.

“Why do girls do this?”

“Dude, I have no idea.”

“But I mean, like when do you figure girls out?” I have to chuckle at that one.

“You never really do,” I sigh. He shakes his head. If he were older, this would be the moment we went for a beer. Maybe several. But I’ve got a job to keep.

“That’s the bad news,” I say.

“What’s the good news?”

“The good news is that you only have to figure out a few of them in your lifetime.”

“God. This sucks so much.”

“Yep. You will feel better, though. That, I can promise.”

“Have you ever had your heart broken?” he asks. I nod and he looks genuinely surprised.

“I know. Even with this face and this hair, my heart has been badly broken many times.” He rolls his eyes. Color is slowly returning to his face.

“Yeah, right. You’re just saying that to make me feel better.”

“Dude, my heart has been broken so many times, it sometimes feels like it’s held together with tape and glue.” I’m an adult and we have the same problem. He’s having a hard time wrapping his brain around this one.

“When was the last time?”

“Just a few months ago.”


“Did you see me cry in class, or crawl up in a ball on the floor?” He shakes his head. “See? I save that for home.” He smiles.

His eyes have dried. This first cry is over. We’re about ten yards from the after school program. He can’t wait out here forever.

“Okay, look. You need to walk in there with your head held high. You gotta fake a big smile. None of this bothers you in the least. Got it?” He nods and takes a deep breath.

“Anything else?” Okay. There is a lot I’d like to tell him. I’m walking that line between teacher and guy, and I know, I should go teacher. I really should. But he doesn’t need a teacher, he needs a guy.

“Yes,” I say. He’s waiting. Hanging on my every word. He’s not a kid. I’m not a middle-aged man. We are two guys with very recently wounded hearts. I pause.

“You know her good friend, Maria?”


“Date her.” He looks confused.

“Sylvia would hate that,” he says slowly. I just nod. For the first time, he actually smiles.

“You didn’t hear it from me. This part of the conversation? This part never happened. Understand?” Now, he smiles almost as big as he did that morning.

“Maria is pretty cute,” he says. Now, it’s my turn to smile.

“You ready?” He nods. “Remember, none of this bothers you. Smile. Say hello. Got it?”

Into the room he goes. I watch him for a moment. This stuff never gets any easier. Maybe it shouldn’t. You can’t know the light, without some darkness. Beautiful new beginnings can come right up out of this sort of dead ash. And, without the evil queen or the dragon to slay, Prince Charming is just a guy trying to get a date. The human heart is, above all else, resilient. I have known the horror stories behind some kids and they still shine with hope. I know older folks, trampled and stampeded on the road of love. Yet, given a little time, they start again. We are all resilient.

“It’s just a little tape and glue,” I tell myself. It’ll hold up just fine.


For more inspiring classroom stories, please check out Mr. Bowen’s recent bestseller, Our Kids: Building Relationships in the Classroom.


Feature image courtesy of Flickr, bailey.foster.

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