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 suffers a breakdown while recalling the discovery of Holly's sister's body. He can also potentially be beaten up by Tweedle Dum/Dee.
The breakdown of Faith and Lawrence's marriage. They were happily married royalty back in the Homelands, but upon their arrival in the Mundane world, things quickly went downhill as they struggled to adjust without help from the Fabletown government. With Lawrence unable to find work, Faith was forced to turn to prostitution at the Pudding & Pie to keep them afloat, and she eventually decided to leave him. Feeling like a failure and a burden to his ex-wife, Lawrence fell into a deep depression, culminating in his attempted suicide so that Faith would be free of him.
While searching Lawrence's apartment, Bigby can find Faith's last note to her husband still taped to the fridge, reminding him when the rent is due, that there's pizza in the freezer, and asking him not to come looking for her.
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.
Hell, Greenleaf's situation in general. She's not selling illegal glamours out of any malicious intent; she's only doing it to keep a roof over her head. And she's so worn down by centuries of being stereotyped as an evil crone that she's just... tired.
Greenleaf: You think I like being the old woman in these stories? The men are heroes, the ladies are whores, and the old hags like me get to watch everyone they love die.
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 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.
Even the ending is not particularly happy! Even if the player picks choices that favor diplomacy and empathy, and avoids getting violent, the final sequence shows that Fabletown's citizens are still very wary of Bigby, if not outright hostile. His final interaction with Snow is very dismissive and cold, and even if you offered Toad money for his glamour, he is sent to the farm along with his young son. Sure, you managed to stop the Crooked Man, but it's hard not to feel powerless when assessing the situation.
