@weyrbound replied to your post: If you don’t mind going into it, what about Scriddler appeals to
you? It’s not a ship I’ve ever really considered - but then, I also
never really thought that hard about riddler ships in general until
Scriddler, for me, has a very strong dynamic. They can keep up with each other. With Jonathan in particular, he can actually outsmart Edward with his psychology knowledge and due the fact he’s likely older and therefore has age-given experience. But he doesn’t make a big deal out of it when he does it. He just leaves it as a thought for Edward to consider and move on. Jonathan can provide Edward with a guidance he needs and I don’t really see him getting from another character. Not really life guidance, but how to manage oneself. I always imagined Jonathan as being very mindful of himself and how to control himself, and I think Edward would want to learn from that. It’s not an easy skill.
Jonathan would be difficult to get to know due to keeping things so close to the chest and Edward would of course regard that as a game and keep at it accordingly. But the more he learned about Jonathan’s history, the more he would respect where he came from and how he got where he is. Jonathan, largely, comes from nothing and makes himself into something. Other characters have done this but to my knowledge Jonathan is one of the only ones who made it before becoming a criminal. Some characters are really good at being criminals but didn’t really make it anywhere legit. Jonathan can do both. Jonathan’s ability to match him both in wit and perception would keep him from getting too bored to either leave or start something just to see how far he can push this thing until it breaks.
Moreover, they really do just plain get along. They don’t fight, they don’t have any real arguments, they only manipulate each other a little and they even call each other for help now and again. They seemingly have this background ‘I’m cool if you’re cool’ sort of thing that makes me believe they could (mostly) peacefully coincide and probably help each other when they’re ready.