Damon and Felicity Challenge 1
Vampire Diaries and Arrow Crossover
Post Vampire Diaries Season 4 Episode 1 + Arrow Season 2 Episode 13
Damon and Felicity have a small but significant history with each other. They became friends after Damon recued her from a mugging and possible raping, but the mugger never got the chance to rape her because Damon killed him quickly with his enhanced speed and strength.
Felicity was in college (MIT) and 19 years old during the mugging incident. In one of the very rare periods of his undead life, he had his humanity switch on and out of instinct he acted somewhat sweet towards her (Just imagine human Damon).
She was shock by his powers but more fascinated and while she did not like someone dying for her, she was not overly upset. She asked how he had powers and out of curiosity in seeing her reaction, he told her that he was vampire. Then she started to babble a bunch of questions like if he was going to kill her, suck her dry of her blood, turn her to a vampire, and other random questions. Without his humanity, he would have found her annoying and probably kill her but with his humanity on, he thought she was adorable and extremely beautiful, which he told her. After telling her that she was adorable and beautiful, she blushed and thanked him.
After their interesting meeting, they develop a pretty close friendship while Damon stays in town. He's stays in town because he is looking for some information about the tomb. Somewhere the down the line he tells her everything about Katherine, the tomb, and that he needs her help with research. She helps him and he leaves, but not without telling her to call him if she is ever in trouble. She wished him luck in freeing Katherine and that she will call if necessary.
She never calls him because she does not want to bother him and she does not want to see him with Katherine because she's fell in love with him. However, she hopes that he find happiness. Damon never notices her feelings because his head is too stuck on Katherine but he does care about Felicity very much.
After Damon's verbal fight with Elena at the end of season 4 episode 1, he leaves Mystic Falls and decides to travel a bit. He leaves his humanity switch on because he is just tired of being a monster (He does not leave his humanity on because of Elena). He leaves his phone behind in his room and also locates a witch "friend" to cast a anti-locater spell on him.
About 1-2 years have past since he left Mystic Falls. He is over Elena and wants to find someone to spend his life with. He sees Felicity on the news standing next with her boss Oliver Queen and decides to visit her in Starling City. He especially wants to see her because of that crazy idiot in the hood lives somewhere in her city.
Damon calls her by a cute nickname which is Angel or Little Angel. Just to make this clear, Felicity developed feelings for Oliver but DOES NOT love him. So, when she sees Damon, she pretty much forgets about Oliver because she DOES love him very much.
There will be about 4-5 months between Arrow Season 2 Episode 13 and 14. When he arrives in the city, Felicity is VERY HAPPY to see him again. Oliver and Diggle will be very protective of her concerning Damon but she will pretty ignore them, especially Oliver. Oliver will end up being pretty jealous, but he just lets it go in the end.
Damon and Felicity will grow from friends to lovers to being in love. They will fall completely in love with each other in the 4-5 month period. They will be completely faithful to each other (No cheating).
Damon will be inserted into season 2 of Arrow and maybe you could add a little AU stuff to extend season 2 before Felicity goes back to Mystic Falls with Damon. Stephan will eventually find Damon and ask for his help in searching for the cure for vampirism.
When Damon and Felicity fall completely in love with each other, she decides to become a vampire to be with him. However, with the news of the cure, he decides to change back to a human to give her the live she deserves. So, Damon and Felicity go with his brother to get his humanity back.
Felicity will be inserted into season 4, 5, and the rest of the Vampire Diaries series. This means that none of the drama or action that happens in season 4 and onward has happened yet.
When Elena sees Damon with Felicity (his Fiancé), her sire bond activates and she starts to cause trouble. However, Damon and Felicity will be completely faithful to each other.