OUAT-Romantic Headcannons 1
(At the time of writing this I have only watched up to Season 3)
What would happen if Rumplestiltskin liked you romantically? This is split into 2 parts, the first is if you reciprocated his feelings, and the other is if you did not. This whole thing makes it sound like hes a yandere or something, but honestly, from what I've seen hes willing to be a sorta violent (towards others) and possessive person when hes with someone.
Honestly he doesn't seem like a very social person at any point that I've seen so far in the series, so I think you will have to meet him through trying to make a deal, or through someone he knows, which will be very difficult.
Despite what he did with Belle while she was under the curse, I don't think he is the kind of person to just start flirting with you. This is mainly because he is insecure about himself (physically not actions wise), and also wants to stay on the track of finding/protecting his son.
I think he's the kind of person who just happens to show up at the right time and place when ever you need any help. He'll try to make a deal with you depending on what situation it is, but every time he tries it either is in your favor, or has something to do with you spending time with him.
If you do end up making a deal, I think he would have you help him find magical objects, or make magic potions so he can have more power. I think he would explain what the objects or potions do, but he would be very careful on telling you where he hides them or exactly how they are created until you know him better. To him, this sort of thing is like a date, away from other people and just between you two.
Even if he tries to get you to spend a lot of time with him, I think his love-language is actually gift giving, he often gets you clothes, jewelry, or magical objects that will protect you.
At first he'd be sort of secretive about his personal life (about his son and how he used to be before he was the Dark One), but after a while he starts to open up to you.
He's not that big on physical affection in public, but makes it clear to EVERYONE that you two are together or that he has an interest in you, if someone tries to flirt with you, he'd get very angry, and probably try to hurt them. I don't think he'd blame you for being flirted with, but he'd definitely ask questions on how you know them.
After you start dating for a while he becomes much more relaxed around you and more comfortable with compliments (calling you beautiful, smart, etc)
I think he is the kind of person who dates to eventually marry (even though this will take a while). And when you do eventually marry, he will try to give you anything in the world.
Just like in Part 1, I think one of the only way that you would meet him would be though making a deal with him, or meeting him though Regina or someone he knows.
Let's say you make a deal with him... During the deal he might try to get to know you more, but if you refuse to tell him much, he will try to make a deal with you that keeps you tied to him, be it taking care of his castle (Like Belle), or something that constantly ropes you into his trouble, but don't worry he will try his best to keep you safe.
While you are around him, he will keep trying to get to know you or give you gifts that would help you, both in whatever task he gave you, and in personal life.
If you still show disinterest in him, he will grow very cold towards you and eventually try to get rid of you (either death or sending you away depending on your relationship), this is because he sees love as a weakness to his plans. But even so, he knows deep down that he had feelings for you and probably wont forget about you, ever.
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