Blu

First of all, both characters would be completely unfazed by the other’s abilities. It just doesn’t seem right that Tomie or Pretty Boy would fall victim to the typical obsession that others have to them. That being said, this doesn’t mean they’d take no peculiar interest in each other.

Throughout the story of Tomie, we see at multiple points that Tomie likes a challenge (e.g. Umehara in the “Gathering” chapter, the youngest son in the “Little Finger” chapter, etc.). She always seems to take interest in going for the ones that don’t show any infatuation towards her. As I said, I don’t think Pretty Boy would have any sort of infatuation towards her. He wouldn’t be at her feet fighting for her love, rather he’d tell her some devastating fortune, and walk away like she’s any regular girl. This, of course, would peak her interest. A mysterious ghostly handsome boy who’s so nonchalant he barely spares her a glance? She needs to study him under a microscope and make herself his only thought immediately.

On the other hand, Tomie does stand out to Pretty Boy amongst all the girls that beg for his fortunes, but only after a while. That being, she never stops showing up at the crossroads. His interest is peaked when he realizes she won’t kill herself in despair like all the other girls he tells horrible fortunes to.

On her end, Tomie would be persistent. She shows up to the crossroads every night, waiting for the Pretty Boy to tell her something like “nobody will ever truly love you.” (which, honestly, probably gets her a bit pissed off, to which she tells him off and he doesn’t respond), and even gets some of her fanboys to track him down (which never works) to either kidnap him or harm him, depending on how mad his fortune made her that night.

On his end, he goes about like normal, telling these girls their fortunes, watching the utter bewilderment at his presence and despair after their fortune is told, and walking with an increased amusement at the sight of Tomie standing there once again. Being completely unaware of her power (curse) to make everyone around her completely obsessed with her, he assumes she is a devoted admirer of him. The difference between her and all his other admirers is that she will never just finally kill herself due to his fortunes. That gets him a bit peeved, and so he is also persistent in succeeding.

Of course, this whole situation does not just affect these two. Everyone around them gets involved. Meaning, all of Tomie’s fanboys get incredibly envious of all the attention she’s giving this mysterious crossroad’s boy, and the same goes for all of his fangirls (“with her otherworldly beauty, surely he’ll fall for her and not me!!”They say). Of course, this causes a lot of discourse amongst the student population in this town.

One person who is definitely affected, especially near the end of the story, is Ryuusuke. If Tomie believes all the gossip that Ryuusuke is the Pretty Boy like everyone says starting around chapter 3 or so, he’ll never be left alone by her. I think, though, she’d realize soon enough Ryuusuke simply does not look or act like the Pretty Boy enough to be him. Maybe in a case where Tomie is involved the rumour would die fast, meaning a lot of the events of chapter 4 and 5 wouldn’t happen the same way they do. Much to think about…

Anyway, as I said before, her interest in the Pretty Boy gets her fanboys extremely envious. As mentioned, Tomie probably tries to get them to hunt down the boy, but this definitely would never work. He is a presence that shows up only to do what he does best (devastating fortunes).

Their envy would build up more and more until eventually, when they need to take it out on someone, that person of course ends up being Tomie. In the typical Tomie manga fashion, she is murdered.

The question is, would this put an end to everything? Well, Tomie would probably just come back. In some cases she’d probably just move and find a new town to terrorize, but Nanchou-Shi is just too peculiar of a town for her to give up. And since Pretty Boy is (most likely) a spirit of some sort, these two have all the time in the world to continue this terrible dynamic.

TL;DR, Tomie and Pretty Boy would have an awfully entertaining and everlasting wild goose chase trying to figure out exactly “what the hell is wrong with this weirdo??”