In case you had trouble finding depressing things on the internet, Bijan Stephen has an article on The Verge that handily links to several sites that trade specifically in the despair and hopelessness online: The feeling of online is ennui
It highlights how you can feel so alone and cold when in the midst of a billion babbling virtual voices. In the era of an American president seemingly spending more time making typos and complaints on Twitter than actually doing his job (perhaps a good thing), it’s not surprising that stories (and sites) like these would pop up.
Screenshots of despair is my favorite, partly because it’s a blog and not a Twitter account, but also because the humor mostly derives from being out of context, which makes it seem a little less hopeless and awful (though the blog author asserts “I am trying to break your heart.”)
One example:
It only gets better from there.