- The second episode with the death of the "Shrine God" because his last worshipper has just died, and there's noone left to pray for him - and even though Natsume offers, it's no good "because you and I are friends". And then we see the final worshipper finally meeting the God in the afterlife.
- And the first episode, Hishigaki calling for Reiko, all alone and crying. Or the youkai who took on a human form to comfort Natsume as a child, only to be rejected by him because he felt deceived by her/it.
- And then there was that part in Episode Six where Natsume cries upon seeing the photograph of the bird Youkai girl he'd grown attached to, finally getting to be with the human she had so badly wanted to meet all her life, if only for a few hours before she vanished.
- The Zoku episode with Gen and Sui... Just... watch it. Particularly Sui's utter heartbreak when the villagers smash her statue to pieces in anger because they didn't stop the famine, even though it wasn't their jurisdiction, and throw the remains off the cliff. This is the beginning of Sui's descent into demonhood as she asks over and over "why?"
- Natsume comforting Gen in the same episode.
- Any moment where Natsume feels less like an outcast and more like he has a place where he actually belongs doubles as both this and a CMOH. Seriously, just, his absolute bewilderment at actually belonging...
- Tama-chan refusing to eat, and Natsume's realization why. Segues into a Crowning Moment of Awesome shortly after.
- The kitsune boy in the manga getting his name turned down, and believing he's useless again.
- The firefly spirit saying goodbye to the man she loved, in the manga, and then dying.
- Of course, the guy used to love her too, and his Anguished Declaration of Love when he could no longer see youkai was equally heartbreaking.
- Natsume and Reiko's life in general. For Reiko, she couldn't trust humans OR youkai and spent the days picking fights to fill the void. It's shown later that while humans called her a freak, because of her strength, even the youkai called her an omen of disaster. At least Natsume eventually found friends among both youkai and humans, but it's implied Reiko never really had that. Although Natsume's life up until that point was harsh as well.
- From the third episode of season one, there was a youkai who took human form so that she could talk to Natsume and comfort him by pretending that she was a human that could see youkai as well. However, once Natsume found out that the woman he thought was like him was actually a youkai...
- The first episode of the third season, Reiko discovering that the old woman she gave her mirror to and was invited to her home was a youkai after all.
- The third episode of the third season has an elementary school classmate of Natsume's come and ask for his help in identifying if that girl he's been seeing is a youkai or not. She is, and in the end, she dies. This doubles as a Crowning Moment of Heartwarming as well because Shibata (the friend) finally believes Natsume's "lies" and thanks him for his help
- Fourth episode of the third season elaborates on Natsume's utterly craptastic childhood, culminating when a prankster tree-spirit plays one trick too many and sends Natsume careening into a complete hysteric breakdown:
Natsume : (Shouting inbetween sobs) Go away. Go away! What did I do to deserve this?! Why do I...? You youkai... I hate you all!
- And just in case there were any doubt about Natsume's Woobie-status, a couple of episodes later we're informed that not only were Natsumes former guardians abusive and neglectful, but even the relatively pleasant ones treated like him like he was nothing but a nuisance. So when the Fujiwaras show up on their own accord and express a genuine wish to take care of him, Natsume promptly breaks into tears of relief.
- Early on in the third series, Natsume witnesses a cute winged Youkai being violently killed by a ravening face. This deeply upsets him, enough that he's still remembering it and being bothered by it episodes later — even after sealing the youkai that did it. It turns out that the winged youkai was deliberately set out as bait for the big one by the Matoba clan, the revelation of which seriously shakes Natsume's faith in humans. Then he meets the woman who was bonded with that winged youkai, who has sworn revenge against the Matoba clan for what they did. She did some serious damage in her rampage, but it's hard not to feel sorry for her when she's doubled over on the ground sobbing for her lost friend.
- Basically, the entire third season seems to have amped up the quantity of Tear Jerker moments
- An attempt to marathon the fourth series ended literally in tears after the fourth episode, with the voice-mimicking youkai and the human woman he wanted so badly to be happy. Especially how after their brief meetings end he goes on a journey to find the place she felt was so much like home and that, upon his return to their shrine she's long gone and he finally learns what her heartfelt last words to him weren't angry or betrayed at all - only grateful.
- In episode 7 of season 4, both Tanuma and Natsume are filled with insecurities and when they finally admit their insecurities, you can just feel and hear the emotions in their voices. This brings them even closer than before and for Natsume is a big step forward in their friendship. This trope teared up.
- The finale of the fourth season, unlike any other arc up to this point in the anime, took three episodes to build up. During climax of Natsume's flashback, Miyuko shouted and screamed at Takashi to get out of her home, and Takashi promptly ran, almost hysterically, to where he thought his old home was, to return to his "real" home, the home he knew is abandoned and empty, with nothing there waiting for him. All the while painfully crying out for his father over and over again. He didn't manage to reach the house that night, and it isn't until many many years later that Takashi came to give the house one last visit before it gets sold, only to break down in tears once more at remembering the short time he had spent with his father.
- Chapter 65, in which an intimidating ayakashi falls for Taki but obviously cannot communicate with her. He wrote a message on her classroom's chalkboard, but asked Natsume to keep it a secret anyway, and refused to say goodbye since to Taki, he essentially does not exist. Those two adorable rat-bunnies only made it ten times more emotional, as Taki kept trying to communicate with the first one and trying to find its friend, despite not being able to see it and not being able to even use her grandfather's circles any more.
The chalkboard message: "I'm lost...you saved me...If it could come true, I would love to bring you to play in that beautiful valley...I wish I could see it with you...this feeling...what do humans call it again?"
- And then Natsume just squeezes his eyes shut and curls up over his desk.
Tear Jerker / Natsume's Book of Friends
Natsume's Book of Friends has tearjerkers aplenty from the very first episode onwards. The sensitive are advised to watch with a wad of kleenex at the ready. Even people who don't cry often would be advised to keep a few kleenex handy.