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1* Alpaca and Vinesauce being rejected in the same ''Tomodachi Life'' stream. Both are rather saddening to watch.
2* Alpaca's life, in general, would be this if it weren't PlayedForLaughs by Vinny. Her feelings have been rejected by both Clown and Walrus, and her girl charm rating got so low over time that it went ''into the negatives,'' and she has turned to cocaine and LSD use for comfort. When she finally manages to find a sweetheart, it just so happens to be Vinesauce, and wanting to fight against destiny, Vinny makes them break up. She finally gets together with [=BonziBUDDY=], however. Then Vinny declares that he'll be killing [=BonziBUDDY=] and that Alpaca will have to deal with it. Vinny soon does so, but Alpaca got with Walrus shortly afterward!
3-->"SORRY, BUT I'M JUST NOT INTERESTED..."
4* Groose and Lamb Chop, the ''only'' married couple on the island for the first 20 streams, get a divorce in Episode 21.
5* Two Faced cruelly abandoning Walrus for Donkey Kong, leaving Walrus in a state of severe depression. Even Vinny, who has done nothing but torture Walrus and treat him like shit since his relationship with Two Faced started, felt bad for him at this point, not hesitating to cheer him up by giving him one of his favourite foods. When he gives Walrus a new interior, Vinny actually sounds like he's on the verge of tears.
6** Making it worse is the montage of Walrus and Two Faced in love, which ended with Walrus sitting alone on the beach, staring out into the sunset.
7* In Episode 38, [=BonziBUDDY=] and Dolan are erased, leaving Levi depressed over the matter. Even when Walrus gets together with Alpaca, Levi doesn't see him as a father figure. He's more accepting of it when they marry, which could double as heartwarming, and hell, even awesome considering all the shit Walrus and [[DrowningMySorrows Alpaca]] went through.
8* Sponge asked Alpaca out. [[spoiler:She didn't even show up]].
9%% These links to the old Booru need to be replaced:
10%% http://vinesauce.booru.org/index.php?page=post&s=view&id=23846
11%% http://vinesauce.booru.org/index.php?page=post&s=view&id=23707
12%% http://vinesauce.booru.org/index.php?page=post&s=view&id=23690
13* Vinny invokes this when displaying a piece of fan art wondering if the Jahns feel homesick, turning up the music ([[https://www.youtube.com/watch?v=96wnpkcZIYw "Searching for Friends"]] from ''VideoGame/FinalFantasyVI'') while it is displayed.
14* Vinny played a ROM hack called ''Super Sponge Bros.'', which is a retread of Mario's original adventure, only with little to no environmental colour besides monochrome and red, ramped up the difficulty, and the game's enemies and [=NPCs=] being swapped out for either depressed ghosts, Mario and Luigi, or even a few cameos of other Vineland Island residents, all telling Sponge that "no princess will ever love him." When Sponge reaches the final castle, he finds out why the princess seemingly left him: She died waiting for him.
15* Small Face and Cling On breaking up after a violent fight (that Groose tries and fails to stop).
16** This was not intentional since wedding guests are randomly assigned and placed, but during Walrus and Alpaca's wedding later in the episode, both Cling On and Small Face can be seen among the guests. On complete opposite sides of the group.
17* It's actually sad to think that Lolly got absolutely no attention during Vinny's stream. In Episode 47, she had her birthday, and that was the first time Vinny noticed her in a long time, and in the following episode [[KilledOffForReal she's lost to the Jahns]].
18* Even after the island is saved from the Jahn invasion by Scully, Mulder, and Vinny, it's hard to not feel bad for those who lost friends and loved ones. Case in point: Seabiscuit, Vinesauce, and Wario lost their significant others, Alpaca lost her only child, and Waluigi lost his (possible) brother. This is sort of made up for the fact that Vinesauce got together with Cling On, and Wario got returned, but in the three's case, it's pretty heart-wrenching to think about.
19* From the very start, ''Survivor Edition'' is prone to this due to its premise. The very first person to get evicted (Dheerse) got some sad fan art despite being seen as a massive {{Jerkass}} during the stream itself. It didn't help that she'd found love in Vlinny. %% These links to the old Booru need to be replaced: http://vinesauce.booru.org/index.php?page=post&s=view&id=36240 -- http://vinesauce.booru.org/index.php?page=post&s=view&id=36265
20** From the same stream, Tingle and Clown Lady split up, with Clown Lady commenting on how people ignore her jokes.
21** Two Faced saying her "Walrus MMMMMM" catchphrase, which was seen as very cruel since she left him for Donkey Kong.
22* Episode 53 includes confirmation that "eviction" is [[ReleasedToElsewhere a euphemism for death]], as Vinny remarks to Two Faced that "it's a 50/50 chance. You're probably going to die... or not. We'll see." Amazingly, the fans were quick [[RescuedFromTheScrappyHeap to sympathize with an islander they hated]].
23%% These links to the old Booru need to be replaced: http://vinesauce.booru.org/index.php?page=post&s=view&id=38160 http://vinesauce.booru.org/index.php?page=post&s=view&id=38150
24* Episode 54 has the evictions of Two Faced and Seabiscuit, both characters divisive among viewers but still with fan followings. Those evictions also reduced the island's female population, even more, reducing the chances for sweethearts and marriages.
25** Seabiscuit's final words were that she and Groose would be besties forever.
26** [[https://booru.vineshroom.net/post/view/27419search=vlinny This bit of fan art]] interprets Two Faced giving the last gold coin needed for Vlinny to visit space as her letting Vlinny fulfill his dream in case he gets removed... knowing full well that she would die.
27* After David Bowie's death, some moments with his Mii become quite sad, such as his Space Charity song, which was about defeating cancer. The real Bowie died of liver cancer. Vinny's forgotten plan to send him to space also stings.
28* The results of a Strawpoll held on January 12, 2016, inspired Vinny to stream the 56th episode and release Music/DavidBowie's Mii [[InMemoriam out of respect]] for the actual David Bowie, who died just two days prior. This manages to be quite heart-wrenching not only because of the real Bowie's death, but because it means that Sponge ended up losing his one and only friend on the island.
29* During the David Bowie special itself (held a week after the real Bowie's death), Sponge lost Bowie, his best friend. This created a ton of sad fan art, but things began to look up when Sponge got together with Clown Lady, who had previously seemed to be dealing with repressed memories (after the Jahns left) and being perceived as unfunny (during the Survivor Edition). What makes this even more heartwarming is how Sponge and Clown Lady are the only people who can see Clown, one of their closest friends. Now, the three can remain friends forever.
30* There's also this small exchange between Vinny and David Bowie's Mii, that leaves Vinny quiet for a moment, and genuinely sounding sad after:
31-->'''David Bowie:''' "I'm still haunted by the horror movie I saw on TV last week..."\
32'''Vinny:''' "That was just a movie, David. Whatever happened last week was just a movie."
33* Somewhere between this and NightmareFuel is [[http://i.imgur.com/r5jT3VO.jpg this fan-made Mii]] -- all of the assimilated islanders, [[BodyHorror fused into a single person]].

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