History BittersweetEnding / WebOriginal

* Campaign 1 of ''WebVideo/CriticalRole'' ends with Vecna sealed away, his cult defeated, and Vox Machina hailed as heroes. However, Vax'ildan - as per his deal with the Raven Queen - must go and serve her in the afterlife. This leaves Vex'ahlia without her brother, Keyleth without her lover, and the rest of Vox Machina without their friend.

* ''WebVideo/DreamSMP'': On both ''[[LetsPlay/{{Dream}} Dream's]]'' and L'Manburg's ends of the SMP war. On Dream's end, he won the war and showed the server who truly held the most power, but L'Manburg got its independence all the same. On L'Manburg's end, it got independence but it also got thoroughly trashed in the chaos (with Dream having earlier detonated TNT under its land), Dream showed that he could easily crush them if they tried anything again, and Tommy ended up having to give away his two prized music disks (which were partially responsible for his feud with Dream to begin with) to secure said independence.

* ''WebVideo/{{Jreg}}'': Centricide 8 ends with [[spoiler: Accelerationism and the centrists all dead]] though quite a few had to perish on the way. The Extremists [[spoiler: also decide to get along and ''not'' fight as the world is their own to control, though by the band getting back together they've restored their status quo in episode 1, much to their shock.]]

* Season one of ''WebVideo/SodorThenAndNow'' ends with all the engines appearing to have survived Patrick Boomer’s attack on Sodor, with Charles promising to rebuild Sodor. On the other hand, Sodor has suffered immense damage from Boomer’s attack, numerous engines have been damaged (with Duck’s fate being left unclear), and Sir Bertram Hatt is dead. Plus, it seems that Peter Boomer (Patrick’s son) has escaped.

* Webcomic/NuzlockeComics invariably end like these, seeing as the protagonist would have lost many friends along the way. No matter how happy the author might try to make the the ending be, it will always be permeated by the feeling of loss and lonliness, both by the reader and the characters.

* ''WebOriginal/TheCrawlspace'', the narrator gets away to safety, but is left with the guilt that she couldn't save her roommates, who disappeared without trace a few weeks after she left. The creature is also likely still at large and might even have escaped the apartment to seek further prey.

* On both ''[[LetsPlay/{{Dream}} Dream's]]'' and L'Manburg's ends of the SMP war. On Dream's end, he won the war and showed the server who truly held the most power, but L'Manburg got its independence all the same. On L'Manburg's end, it got independence but it also got thoroughly trashed in the chaos (with Dream having earlier detonated TNT under its land), Dream showed that he could easily crush them if they tried anything again, and Tommy ended up having to give away his two prized music disks (which were partially responsible for his feud with Dream to begin with) to secure said independence.

* According to Lily's Proposal of SCP-001 in the Website/SCPFoundation, [[TheEndOfTheWorldAsWeKnowIt this is how the world ends]]. According to the proposal, "The World's Gone Beautiful", SCP-001 is a phenomenon that will occur exactly 24 hours before the death of all life on the planet (from what isn't known, but it's likely that SCP-001 is unrelated and more just a PortentOfDoom), which causes unusually beautiful and vibrant flowers to bloom across 90% the world's surface, all air pollution to dissipate, and for all the living to feel a sense of calm toward their impending doom. All SCP staff and any sapient, non-aggressive [=SCPs=] will be released and allowed to walk free to spend their last day however they please, ensuring that the world will be beautiful one last time before it all ends.

* [[https://www.youtube.com/watch?v=V2RytpvQ9BA "The Domino's ad that vanished from YouTube"]] ends with Nick Robinson reaching the UsefulNotes/{{Tokyo}} headquarters of Domino's Pizza only to realize that Scott Oelkers, the CEO of the company and star of the commercial, had retired before Nick was able to meet him. At first, it seemed as though Nick [[ShaggyDogStory was left with no answers]], until he realized that Scott's retirement ''was'' the answer: because he starts off the video introducing himself as "President of Domino's Pizza", it was taken down since it contained outdated information. Further making this bittersweet was the bouquet of flowers he saw in the company lobby, where Nick had made the attempted call to Scott: he realized after the fact that those flowers were a "parting gift from other people who loved Scott just as much as [he] did", and that Nick had MissedHimByThatMuch. Despite not being able to meet his idol in person, Nick was nonetheless satisfied with the conclusions he was able to derive from his investigation, and able to see second-hand the impact Scott had made on others outside of his silly commercial.

* At the end of ''WebVideo/PrettyDudes'', Zario and Jay take off together, not only leaving behind their LA problems, but also all of the friends who care about them, including the ones who nursed Zario during his bad trip ''that same night''.

* ''WesternAnimation/RedVsBlue'':

* According to Lily's Proposal of SCP-001 in the Website/SCPFoundation, [[TheEndOfTheWorldAsWeKnowIt this is how the world ends]]. According to the proposal, "The World's Gone Beautiful", SCP-001 is a phenomenon that will occur exactly 24 hours before the death of all life on the planet (from what isn't known, but it's likely that SCP-001 is unrelated and more just a PortentOfDoom), which causes unusually beautiful and vibrant flowers to bloom across 90% the world's surface, all air pollution to dissipate, and for all the living to feel a sense of calm toward their impending doom. All SCP staff and any sapient, non-aggressive SCPs will be released and allowed to walk free to spend their last day however they please, ensuring that the world will be beautiful one last time before it all ends.

* In episode 100 of WebVideo/ScottTheWoz, titled ''It's Awesome Baby'', [[VideoGame/MaddenNFL Madden 08]] [[ItMakesSenseInContext is destroyed forever in exchange for a timeline where people aren't legally forced to love Dick Vitale's Awesome Baby College Hoops.]] It gets subverted though, as Scott wins a sweepstake to make whatever game he wants.

* ''Machinima/ArbyNTheChief'':

* ''Machinima/RedVsBlue'':

* "Machinima/ShadowsOfThePast" at the end of season one after the two assassins trying to kill them and a giant mech with a crazy A.I and a mission to kill all "idiots" within a hundred mile radius are defeated. Venus is accepted into their group as a friend despite her betrayal and everything is shaping up to be a happy ending. Until the box. Sage activates an ancient piece of technology that transports him to yet another unknown world where alternate versions of his "friends" knock him out and drag him away.

* ''WebVideo/Jreg'': Centricide 8 ends with [[spoiler: Accelerationism and the centrists all dead]] though quite a few had to perish on the way. The Extremists [[spoiler: also decide to get along and ''not'' fight as the world is their own to control, though by the band getting back together they've restored their status quo in episode 1, much to their shock.]]

* [[https://www.youtube.com/watch?v=V2RytpvQ9BA "The Domino's ad that vanished from YouTube"]] ends with Nick Robinson reaching the UsefulNotes/{{Tokyo}} headquarters of Domino's Pizza only to realize that Scott Oelkers, the CEO of the company and star of the commercial, had retired before Nick was able to meet him. At first, it seemed as though Nick [[ShaggyDogStory was left with no answers]], until he realized that Scott's retirement ''was'' the answer: because he starts off the video introducing himself as "President of Domino's Pizza", it was taken down since it contained outdated information. Further making this bittersweet is the bouquet of flowers he saw in the company lobby, where Nick had made the attempted call to Scott: he realized after the fact that those flowers were a "parting gift from other people who loved Scott just as much as [he] did", and that Nick had MissedHimByThatMuch. Despite not being able to meet his idol in person, Nick was nonetheless satisfied with the conclusions he was able to derive from his investigation, and able to see second-hand the impact Scott had made on others outside of his silly commercial.

* In episode 100 of Scott the Woz, titled ''It's Awesome Baby'', [[VideoGame/MaddenNFL Madden 08]] [[ItMakesSenseInContext is destroyed forever in exchange for a timeline where people aren't legally forced to love Dick Vitale's Awesome Baby College Hoops.]] It gets subverted though, as Scott wins a sweepstake to make whatever game he wants.

* In episode 100 of Scott the Woz, titled ''It's Awesome Baby'', [[VideoGame/MaddenNFL Madden08]] [[ItMakesSenseInContext is destroyed forever in exchange for a timeline where people aren't legally forced to love Dick Vitale's Awesome Baby College Hoops.]] It gets subverted though, as Scott wins a sweepstake to make whatever game he wants.