- Toad Jr. has a very troubled life. His dad's a total prick who doesn't know enough to spend his money wisely and refuses to accept responsibility for it, he lives in a run-down Noir city, and he's shipped off to the farm at the end of the season no matter what you do, thanks to his Jerkass father. He can also potentially be beaten up by Tweedle Dum/Dee.
- Vivian's suicide by way of removing her ribbon in Episode 5, and the entire scene surrounding it, including the exposition of her Dark and Troubled Past, as well as Georgie's reaction to her death:Vivian: I'm sick of everybody thinking that they can just— do what they want with my life. I thought it would be different here. But it's all the fucking same. Do you think I wanted to be this person? What I did to Faith and Lily... to all of them... Every day I have to look Gwen and Hans in the eye and pretend I don't care. I have to forget what I've done to them. What I took away from them. I look at Nerissa and I hate myself. I can't pretend anymore. Goodbye, Georgie.
- Georgie's death scene in Episode 5. He may be a Grade A asshole as well as the killer (making him a major antagonist in the game), but the physical and mental anguish he feels in his last moments are heart-rending - he may be a monster, but he's still human enough to sympathize with him and the soul-rending anguish he goes through while slowly dying of disembowelment right after accidentally driving the only woman he ever truly loved to kill herself. His last moments are an even bigger dog-kicking. You can either leave him to die slowly or finish ripping his guts out, which, while faster, is clearly absolutely agonizing. Apparently, Bigby doesn't believe in using guns.
- In a fridge sense, the reason Woodsman left town in episode four might have been that his friendship with Holly and Gren was irreconcilably shattered when they found out that he was a frequent customer to Holly's prostitute sister, Lilly.
- In the end, if you decapitate the Crooked Man after bringing him in for his trial leads to Fabletown being scared of you. All the work you (might) have done to get people to trust you, feels all for nothing. When going past the Fabletown Offices the next day, no one but Gren looks happy to see you and if you try to apologize to Snow about killing the Crooked Man, she has no time to listen. Even during the final conversation with Nerissa at the end of the game, Bigby can admit he doesn't know where he and her stand.
- Holly's reaction to her sister Lily's death in the comic adaption. In the game, she takes the news stoically. In the comic, the shock causes her glamour to fail. Then the Trip Trap's jukebox starts playing Simon & Garfunkel's The 59th street bridge song, and remembering that it was Lily's favourite song, Holly finally breaks down in tears.
- Burning down Aunty Greenleaf's magic tree on Snow's command in episode 3. Really take a good luck look at Greenleaf's face when her single source of income (making black market glamour spells from the tree) gets burned to a crisp by you. Snow even looks ashamed of commanding you to do this.
- For added bonus, that is her family heirloom.
- A minor one, but when Bigby asks "How much longer is this gonna go on?" He just sounds so tired and defeated by everyday life grinding down on him. No mail for the past seven days, everyone is afraid of him. It can't be easy.
- Bigby's apartment is also depressingly run down. He has little if any personal affects beyond basic necessities. And its a known fact that he lives in the 'smallest apartment in the Woodlands'.
- A strange one would be if Bigby kills The Crooked Man before the trial then if the player chooses to leave the courtroom then Bigby will call out on all the citizens actions and how they complain to Bigby and Snow despite how much the pair try to help (in his words "we've been through hell trying to keep you all safe and to make you all fucking happy but all you do is complain, so fuck this!"). It's somewhat heartwarming and tearjerking at the same time because he finally stands up for himself and makes his own decision but it's tearjerking for Bigby as this is how much the story and his job has affected him.
- A Meta Example: Following an extremely long hiatus and a large amount of vocal desire by the fan base, Telltale Games announced The Wolf Among Us Season Two, to great positive opinion and anticipation. Then, in late September 2018, Telltale announced that they were preparing to close their doors and that all in progress projects, including The Wolf Among Us Season Two, were cancelled.
Tear Jerker / The Wolf Among Us