The fact that Jude and Joey haven't seen their father in years is somber. Especially since those knowing Homestuck canon will know that he'll soon possibly ditch them entirely for their half-sister Jade.
It gets worse when you inspect the blue lady portraits in the basement since the description all but states that that's exactly what happened.
Joey's narration: PA loves his BLUE LADIES portraits so much, he keeps redundant backups scattered around. Because it's ok if you ignore something supposedly precious to you, as long as you're paying attention to something kind of similar, in another location, right?
It gets even more worse when you realize that every single one of these characters, if they survive Hiveswap, is either going to die via meteor due to the Beta Kids entering the Medium or due to the Vast Glub when the trolls begin their Session.
Pretty much any dialogue from using items with the picture of Joey's mom. It is, for the most part, somber and devoid of snark.
Diary Key: You should write more about how you feel about your mom, and your mom being gone, and all that stuff, but... it's not easy.
Walkie Talkie: You... yeah. You really wish you could.
Ballet Shoes: [...] Though she passed when you were really young, before you could ever see her dance, you have a few tapes of her performance, and you could, of course, track down more... but... you know that only so many of her performances were recorded and once you see them all, that'll be it. You won't ever see your mom doing anything that's new to you again. So you save them. If you're patient... if you're really good, and you save them for the absolute best days (the ones you want to share with her) and the absolute worst days (the days you just really, really need to see her)... then you might be able to make them last a long, long time. You hope.
Clicking the picture of tiny Joey brings up similar sadness:
That little girl there? She's destined for big things. Big hopes. Big fears. Big worries. Big lonelinesses.
Now hold on, pull yourself together. What would your MOM say if she knew you were thinking like that?
You really wish you knew.
Jude's pigeons dying or flying away becomes this when you realize that this kid just essentially lost his pets. He sounds like he's about to cry when he talks to Joey over the walkie-talkie and he begs her to protect the only one he has left instead of risking a return trip.
This happens again when Joey indicates to him she won't be able to resist messing with the portal due to how he knows it could be dangerous and the way the walkie-talkie's signal starts breaking up. Given the plot of course what happens is exactly what he's afraid of, as the only real human constant in his life is beamed to another planet in another universe entirely.
Jude: Joey ple... I ca... ose you to...
Joey's second victory over the monsters is this. Even as triumphant music plays, the victory text makes it clear how close she is to a nervous breakdown.
This discussion of the Game Over scene and Joey's determination to do no harm:
Look at her face. She is not angry. She is resigned. Her expression may have been a joke, but I feel like struggling and fighting would make the Game Over scene much more horrible. Hussie did not depict her struggle for a reason.
Her face says, “Woop, I’m sorry, but I can’t do anything about my current situation. Fighting back would make me like my dad, who is the worst person in the universe, and I’d rather get eaten than get compared to him.”
Xefros is the most chipper, upbeat kid, even when crushed under a pile of rubble and in mortal danger. Whether he's really that affable, conditioned to accept his lot, or just putting on a face, he doesn't deserve the life he's been handed.
Despite ostensibly being a rebel, Xefros is quick to put himself down as "rustblood trash." He seems to really believe that he's merely a servant who should be grateful for what little he's been given. And Joey - not his supposed best friend Dammek - is the first person to ever tell him otherwise.
Dammek and Xefros' "friendship" isn't actually all that great. Dammek basically controls everything about Xefros' life, takes his things to make them his own, and doesn't seem to have tried doing anything about Xefros' cripplingly bad self-esteem despite being his Moirail. Based on what we've seen so far, Dammek is an unbelievably terrible friend.
Talking to Skylla on the train will have her say that her lusus is ill and likely won't survive the journey. It's especially sad if you've played Friendsim and seen how good of a relationship Skylla has with her.
Getting a mistrial makes sure that no one dies in that segment, but it doesn't come without damage. While Daraya and Lanque point out that Lynera is well-aware that the others hate her and complains about it all the time, this is likely the first time Lynera's realized that most of her cloister-mates want her gone so badly that they're willing to let her die and make arrangements for it to happen. Furthermore, the issue clearly isn't just Lynera; it's made clear that most of the jadebloods don't really like each other.
In addition to being a traumatizing event, Joey is also hurt by being forced into the Purplebloods' game by Marvus. If she talks to him after being given the task of killing a Tealblood, she tells him that she thought they were friends, and says that she's not sure that's true anymore when he says they are.
Barzum does not take Baizli's death well at all. When Xefros and Joey return to the purple car, she's writhing in agony on the floor. While he was killed in self-defense, it's easy to forget that the Soleil twins are on the younger end of the Troll Call trolls.
of the Game Over scene and Joey's determination to do no harm:Look at her face. She is not angry. She is resigned. Her expression may have been a joke, but I feel like struggling and fighting would make the Game Over scene much more horrible. Hussie did not depict her struggle for a reason.Her face says, “Woop, I’m sorry, but I can’t do anything about my current situation. Fighting back would make me like my dad, who is the worst person in the universe, and I’d rather get eaten than get compared to him.”