Obey Me! headcanons

Undates falling in love

Diavolo:

-He falls in love quite quickly. It's not instantaneous, and it takes a while for him to fully trust them, but it happens soon enough for him to be able to take note of the things they like before asking them out
-While he can't avoid his princely duties forever, he'd gladly spend whatever time off he has bonding with MC
-Bonding can be whatever MC wants to do; shopping? He's paying. Feel guilty for him paying? He's lecturing you about how much you mean to him. Cuddling? He won't let you go for hours. Reading? His arms are already full of books.
-Not super obvious when he's in love, but you can tell if you pay enough attention. Generally pretty composed until MC does something cute and he gets all flustered
-Seriously, MC can affect him like nobody else
-He really wants to take MC everywhere with him, mainly to show them how wonderful things can be at the Devildom

Barbatos:

-Not obvious at all, except maybe to Diavolo, Lucifer, and occasionally Asmo
-He falls relatively slowly, but still quick enough that it sneaks up on him before he gets a proper chance to figure out what he wants
-Doesn't deny it, especially if someone asks, but he responds cryptically and vaguely if MC is somewhere nearby. He's not scared, since he knows the future, he just doesn't have the time
-Subconsciously, he starts making more and more things for MC. It's not like he'd randomly show up with gifts or anything, he's more subtle than that. No, he hides it with a "I'm testing a new recipe", "My Lord requested this and there was too much leftover", or "I need a taster for my human realm recipes"
-Once he has time to recognize what he wants, he'll be incredibly direct with MC. He'll give them things and tell them flat out that he made it for them

Simeon:

-One of the slowest to fall, believe it or not
-He's in pretty heavy denial because on one hand he really doesn't want to fall and then on the other hand he doesn't want to hurt MC because they won't live forever like he will
-Everyone knows, often including MC. It depends how oblivious you are, but the signs are all there. That being said, he tries to hide it for a while in an attempt to spare MC's feelings
-After a while, Solomon chats to him about his awfully obvious feelings for them. Simeon takes some time to think about it and realises that he can't just sit and suffer in silence, so he tells MC how he feels with a nice dinner

Solomon:

-Shady Wizard doesn't realise he's in love until Asmo points it out to him
-He sneaks so many glances & soft touches that it's a wonder how nobody other than Asmo noticed. I mean, seriously, you'd think with how all the brothers distrust him they'd keep a closer eye on him
-He's actually pretty protective, giving them enchanted items of protection, holding their hand while they're studying, speaking up for them, death glaring lesser demons
-Honestly give him the chance and he'd face off against the brothers, maybe even Diavolo if he felt the need to
-Okay maybe not an actual full fight, more like threats and inconvenient pranks, but still. It's the thought that counts
-He's the only one who'll flat out tell MC with no help. No treats, no fancy stuff, just straight up "MC, I have feelings for you."