CR chart
RELATIONSHIPS
Positive
Mireille Duroc
Silver Wolf
"I'm pleased that others here are capable of being rational."
On the whole, Nathaniel likes Mireille. He thinks she is sensible and rational, unlike many other citizens of Adstring. While he respects her thoughts and ideas, he's still not sure what to think of her being married to Jean Louis (see 'Unsure'). He enjoys speaking to her, and her prim and proper way reminds him of his secretary at home. As such, he's comfortable bouncing ideas off of her and asking her opinion on things.
Hino Rei
Sailor Moon
"I meant it when I offered my help."
Nathaniel likes Rei, he genuinely does. She seems to have her head on straight, as well as be willing to help him change things for the better. He doesn't know much about her, but the more the two of them talk, the more he finds himself agreeing with her words. He has a feeling that she will be a very useful ally when push comes to shove. He also gets a little flustered around her because what are females.
Raven
Teen Titans
"You have my gratitude."
Raven was the one who initially saved his life (?) when Nathaniel crash landed in Adstring with mortal injuries. She is also the only person to know that Nathaniel is dead. He trusts her to not share that information with anyone- but only because he has to, as he didn't really have an option of not telling her. Nathaniel still isn't sure what exactly she is, and he's a little apprehensive about her powers (as well as unable to shake off the idea that she is a spirit), but ultimately, he considers her an ally and a good choice for one of the police unit leaders.
Hermione Granger
Harry Potter
"I hope that the progression of this government meets with your approval."
HE LIKES HER, HE REALLY DOES, BUT NATHANIEL IS AN AWKWARDTURTLE FOREVER THE END.
Unsure
Jean Louis Duroc
Silver Wolf
"I've known too many people in positions of power to put much stock in altruism."
John Mandrake wants to like Jean Louis. A lot. But he uncomfortably reminds Nathaniel of the magicians he used to serve- he's intelligent, devious, ambitious to a fault... and he wants to convert their budding police force into a military dictatorship of sorts, so that he can exert his power and influence over the people. Nathaniel sees a lot of himself in Jean Louis, and that scares him- but he also respects him for his intelligence and his political manner of speech and action. Of all of Nathaniel's relationships, Jean Louis is the man who makes him question his own thoughts and actions the most. For now, he remains polite and agreeable to Jean Louis, but who knows how long that will last?
Tom Riddle
Harry Potter
"Fascinating form of magic."
Nathaniel thinks that Tom is a pretty swell guy, but there's more than an inkling of doubt here and there. Nat isn't stupid, and he knows how to do his homework on someone- there's more than a little mistrust of Tom going on around the network, especially amidst other members of the Harry Potter cast. But Nat continues to speak with him, seek his advice, share their knowledge of magic, and ask him to participate in the government, because Tom is a rather likeable guy. Although Nathaniel won't put himself in a position to be hurt by Tom (that he's aware of, he doesn't know about all of the intricacies of Riddle's magic), he will consider him an ally until he personally has a reason to believe otherwise.
Castiel
Supernatural
"...you're one of the angels everyone keeps talking about, aren't you?"
Nathaniel isn't sure what to think of Castiel. Firstly, Castiel is/was an angel. And Nathaniel doesn't believe in angels on principle. Secondly, Castiel has proven that he cannot be trusted. But, ultimately, Nat sees somewhat of a kindred spirit in the him- not only is Castiel a good source of information on the afterlife, but he is also just as socially awkward and tl;dr as Nathaniel himself.
Unohana Retsu
Bleach
"...I'd like to thank you for healing me, but I think it's time I took my leave of the clinic.."
Nathaniel's first meeting with Unohana did not go so well. She thinks him presumptuous and arrogant, and he thinks her old fashioned and pessimistic. Still, she did heal him, and she shows no sign of a grudge toward him in their later conversations. So he'll be nice to her for now, but he's still wary of getting even further on her bad side.