“El reading Hopper’s letter at the end of Season 3 absolutely destroyed me.” That’s how one Redditor goes, summarizing one of the terrible heartbreaks of Stranger Things. Reading that, I couldn’t think of anything but ranking the most gut-punching Stranger Things moments, tear-stained moments, and emotion-laced dialogues – from the scale of least to most emotional moments.
The saddest moments of Stranger Things
Rated based on the no. of tissues you require – from a few to a bunch and more.
Will’s endless trauma
Will’s trauma isn’t just a one-season plot — it’s a permanent shadow over his life. From Season 1’s “Mom, it’s me… I’m right here” in the Upside Down to Season 4’s quiet car scene where he turns away tears while telling Mike, “You’re the heart,” it’s clear he’s still carrying isolation, fear, and unspoken truths. The worst part? Everyone else gets to move on between monsters, but Will never truly leaves the darkness — it’s still in him, lurking, like the Mind Flayer is just waiting for round two.`
Surprising theory: quiet, artistic, spends a lot of time alone, and feels like an outsider – what exactly made the Mind Flayer choose Will. The Demogorgon supposedly hunts by sensing fear, and Will’s lonely bike ride on that rainy night in Season 1 made him an easy psychic “blip” in its radar.
Jonathan and his share of loneliness and trauma during initial days
Remember in Season 1, Episode 4 (“The Body”), Jonathan is seen sitting alone in his room, developing the photos he took in the woods. The images show Will’s friends, carefree and laughing — a world Jonathan can observe but never quite be part of. Then he catches sight of Nancy smiling at Steve in one of the photos. He lingers on it just a little too long, that quiet sting of knowing she exists in a space that feels unreachable to him. No words, no music swell — just silence and isolation.
We all been there. Unrequited love and one-sided emotions. All while there is turmoil boiling in his home, with his brother gone missing, mom acting neurotic, and the fatherly figure being entirely absent.
Many men could relate to Jonathan’s teenage struggles and bottled-up emotions, which pretty much shapes up his future even when he is in a stable relationship with a girl like Nancy.
Steve always being the guy left behind
It’s weird, watching Stranger Things and realizing Steve Harrington is basically me in a better jacket. You’re there for everyone — the late-night drives, the “text me when you get home,” the listening ear when their heart shatters. But when the dust settles? They go home to someone. And you… you just go home.
There’s a scene in Season 3 where Steve is in the back of the Scoops Ahoy shop after Robin comes out to him. They laugh, they share this beautiful honesty — and then she starts talking about her crush. And you can see it: the shift in his eyes. He smiles, he’s supportive, but in that moment, he quietly tucks his own feelings into a box he’ll carry alone. That’s the Steve life — you’re happy for people, you’re genuinely happy for them, but you’re also wondering if anyone will ever look at you the way you’ve looked at them.
People can’t wrap their heads around Steve Harrington being single — he’s attractive, kind, loyal. But that’s the point: life isn’t a fair equation. Looks and a good heart don’t guarantee love or success. Sometimes, being “the perfect catch” just means you’re the one holding everyone else’s net.
Max’s death
Max’s “death” scene in Stranger Things S4 is one of the most chilling, emotionally charged moments in the entire series — and it’s not just because of the horror visuals.
In the Creel House showdown, Vecna finally gets his claws into her. We watch, powerless, as Max’s body begins to twist in ways it was never meant to. Bones crack one by one, her arms and legs snapping like brittle sticks. Blood wells in her eyes, blinding her. The sequence moves in slow motion, the kind that forces you to take in every agonizing detail.
The cruelest gut-punch isn’t the gore — it’s her voice. Through labored, broken breaths, Max manages, “I don’t wanna die.” In that moment, she isn’t the cool, sarcastic skater girl. She’s just a terrified teenager who wants one more day. And the way Lucas is holding her, shaking, begging her to stay? That breaks you twice over — once for her pain, and again for his helplessness.
Hopper’s letter to Eleven
Hopper’s letter to Eleven is already heartbreaking on paper, but when you remember where both of them came from, it becomes devastating.
El had spent most of her life as an experiment, shut away, treated like a weapon instead of a child. Then, she finally found a father figure — not just someone to protect her, but someone to give her messy dinners, silly rules, and the kind of grounding love she’d never had.
Hopper, on the other hand, had lived years in grief after losing his real daughter. When El came into his life, she didn’t just fill a void — she gave him a reason to hope again, to fight again. In the letter, he talks about change, about growing, about the inevitability of pain. It’s not just the loss of a father or a daughter — it’s the shattering of the first real family either of them had.
Bob’s death right after being a hero
Bob wasn’t just a boyfriend for Joyce — he was a safe place in a world that had chewed her up and spat her out. For women like me, hopelessly romantic but carrying battle scars, he was proof that maybe, just maybe, someone could walk into your chaos and fit perfectly, like the last piece of a stubborn puzzle.
He cracked jokes, made breakfast, and made you believe the worst was behind you. And then, right after saving everyone, he was gone. No warning, no goodbye. Just like that, the man who made you feel safe left you standing in the rubble, alone again.
The one last moment of his smiling face before he was devoured by those demogorgons, who he had no idea about – that’s an image a Stranger Things fan will never forget.
Sean Astin, who played Bob, shared at a Fan Expo panel that Stranger Things creators Matt and Ross Duffer were in tears as they wrote the heartbreaking scene that ends with the simple line: “And Bob stops running, period.”
Alexei’s death at fair
Alexei’s death at the fun fair stung because he felt like an innocent child finally allowed to play outside after years of being locked away. He barely spoke our language, but his wide-eyed curiosity said everything.
For the first time, he wasn’t the hunted scientist — he was just a man laughing at winning a stuffed prize in the shooting game, soaking in the sights like they were proof he’d made it to safety. And then, in the middle of this borrowed joy, the danger he thought he’d outrun found him. The fair music kept playing, but Alexei’s game was over. That smile when he won the stuffed toy, moments before his demise, is priceless though.
Eddie and his last guitar solo
The world will never understand people like Eddie, and it’s okay. A guy who didn’t just succumb, but did something magnanimous – something that made him more than the “freak” Hawkins called him. He could have run. He could have gone with the plan.
And yet, there he was, in the blood-red sky of the Upside Down, playing “Master of Puppets” like it was the only thing keeping the world from collapsing. Every riff was loud enough to make you forget he was just a high school outcast — in that moment, he was a legend. All the while, I was shouting at the screen, begging him to run for his life. 😭
There you go, Eddie Munson’s death is the saddest and most gut-wrenching moment of Stranger Things.
Final thoughts
Stranger Things has a way of giving us characters who feel like friends, family… even pieces of ourselves. And when they go, it’s not just about the story losing someone — it’s about us losing them. These moments hit because they remind us that bravery doesn’t always win, good people don’t always get their happy ending, and sometimes the ones we love the most are the ones we have to say goodbye to too soon. But maybe that’s why we hold onto them so tightly — because even in fiction, they teach us how precious the real thing is.