This story has been cancelled as a reboot involving many plot and character changes is replacing it. Link here: https://www.fimfiction.net/story/462928/tales-of-troubled-teens-reboot
(Alternate universe set before any of the events of the Equestria Girls movies.)
Meet Pocket Pair, a teenager high school student with an obsession over playing poker. One thing about him you may want to know about him, among the many other things there are to know, is the fact that he has Asperger’s syndrome, a form of autism. Among other things, this means that certain things, such as socialization, do not come nearly as easily to him as they do to most people, and as a result of this he has had great trouble making friends for a vast majority of his life, even up until his senior year of high school. Granted, he does have two people who call themselves his friends named Applejack and Ralph, and he sits with them every day at lunch. However, he does not believe they are really his friends since they very rarely talk to him outside of school and never actually invite him to do anything. Feeling bitter, upset, depressed, alone, and oh so desperate for change after a lifetime of not feeling he has friends, on the eve of his senior year, he makes a plan to make things better before he graduates. The plan is simple, get a girl, woo her, and then the love from the relationship should make things better… I mean after all, it works in all the Hollywood romances he watches after all…. Unfortunately, when he shares his plan with his table mates Ralph in particular takes offense to it, feeling it is just a pathetic attempt by him to get them to feel pity for him and give him attention, even though Applejack feels otherwise. Pocket Pair, fed up with Ralph’s failure to meet the standards he feels he should, tells him to put his money where his mouth and demands he make a bet with him on this or shut up for good about it, even offering to give him a choice to say who he needs to ask out with it. Unfortunately for him, this was a HORRIBLE mistake, because Ralph is so fed up with his “attention ploys” he’s going to make dead sure, he never makes another one And how will he do that? By making Pocket Pair ask out the girl who is BY FAR the meanest in the entire school … SUNSET SHIMMER!!!!