Oliver's App: http://159.65.241.122/index.php?threads/9486
Alex: I think that he and Oliver could become more or less friends, and the sadistic bit of personality in him can actually be used in his favor. Given Oliver’s dark secret he wouldn’t mind to have someone that more or less shares this trait.
Max: They both share a really nice imagination trait, and he may not look like it, but Oliver can be quite a good candidate to get philosophical with…as long as you can handle his overly optimistic way to see the world and his obsession for sweets, especially cupcakes. He is also a bit too friendly, so her aloofness will just slide.
Marco: Oliver will obviously feel interest towards him and his multiple personalities, and probably wouldn’t mind to meet them all. However, be careful, he may let some mistakes slide, but you don’t want to get on his bad side. He will probably warn each personality once each time they take a wrong step, but that’s mostly it. If you push your luck too much with him when he’s angry you may not make it out alive.
Jaya: Both an influence and provider. He can give her “Special cupcakes” of the drug kind if she manages to find out about his little secret without getting herself in lethal danger. He can also be quite a confusing influence given his personality.
I’m also eyeing a couple more of your charries, but those are the ones I have more stable ideas about. If you have another idea I didn’t managed to get just say it!!!