request: any advice on what episode to introduce and OC to the supernatural in?
so there's a few things you want to consider here:
1. when does your fanfic take place?
it really depends on your story and what you want to tell to decide when it should take place.
for example, in my kol mikaelson fanfic i wanted it to take place when he arrived. so it begins when he is undaggered in season 3.
now could i have started it sooner? yes. but it was a kol fanfic and i didn't really want to start at season 1 and work my way up.
this might just be a personal preference, but when i start a fanfic and it starts several seasons before the love interest is even on the show, i won't continue reading. i imagine i'm not the only one.
but if i was starting a bonnie fanfic, i might start at season 1.
it also depends on who your oc is. if your oc is a mikaelson then it might make sense to start your fanfic in season 2 or 3 when they arrive. if you start before you'll have to think about why they're in mystic falls, why they haven't been daggered, why they're not with klaus or elijah etc.
you could also start your story when the mikaelsons are turned or sometime back then. i would personally advice against that. because that means you have a thousand years to get to the events of the show. we also only get flashbacks of their time before the show. you don't have all the events on what they were doing. realistically, you aren't going to be able to cover a thousand years. it's better to stick to the flashback format as that's what they use in the show.
2. what is your ocs relationship to the other characters?
might just be a personal preference, but i hate when the oc is kept in the dark for a very very long time.
all of the main characters on the show knew by season 3.
elena, bonnie, and jeremy learned in season 1.
tyler, matt, jenna, and caroline in season 2.
so if you're on season 4 and they still don't know it's a little odd to me.
my oc didn't know until season 3, but that was because for reasons i don't want to spoil, she was being compelled to forget whenever she learned. 
but as time went on it got increasingly dangerous for her not to know.
which is something you want to consider.
at some point it becomes unrealistic that they haven't been involved at all if they're incredibly close to the main characters,
for example, if elena had a sibling they're definitely going to get dragged into it at the latest season 3.
i don't remember katherine going after jeremy but she did go after jenna. so did klaus. klaus also went after caroline.
so unless you give a reason for these characters to not involve your oc, it's going to be incredibly difficult.
not to mention that their lives are heavily intertwined with the supernatural so your oc is going to be left out and there's only so much of that they can take.
3. as for the actual moment, you have to think about what you want.
it's difficult to say what the "right" moment is because it's different for every story.
for me it was because the story was speeding up and it was increasingly difficult for my oc to not know and for others to keep it from her.
for example, she had just kissed kol and wanted to start a relationship with him right before she found out. he didn't tell her, but he would have to once they entered into a relationship.
(spoilers for my fanfic) 
she found out because she got stuck in the school when esther put on a spell on it at the end of season 3. she was supernatural but didn't know it. later she found alaric when he had kidnapped caroline.
4. think about how you want it to impact your oc.
there are two ways your oc will learn about it. either they're told or they witness it.
do you want it to be an intense moment for your oc?
or do you want something more calm?
for example, if you're writing a klaus fanfic that isn't exactly tied to the events of the story, then you might have it be a moment where he comes clean, he's honest with your oc, maybe it's a cute moment, maybe it's sad, it's whatever you want.
but you should also consider what makes someone tell your oc?
again, in my fanfic my oc witnessed it so they had to tell her. kol refused to compel her and didn't let anyone else do it either. 
but if nothing forced them to, then what's the reason?
were they feeling guilty about keeping a secret?
did the character finally feel they could trust your oc?
maybe they were in a relationship that was getting serious?
those are just some things to consider.
i personally regret going with a more dramatic scene. i wish i had written it where kol told her. i think it could've helped their relationship.
if they don't tell your oc, remember that you'll also have to deal with the potential fights that could come with that. your oc might feel like they were lied to and betrayed. like they weren't trusted.
the way they're told could also majorly impact how they process it, which i already talked about.
5. as for the actual episode, i don't think there's a right answer.
i think it depends on the stuff above. if you're going for something more dramatic, then one of the more eventful episodes.
could also be linked to an episode where something big happens to a character your oc cares about.
for example, let's say your oc is caroline's sister. caroline might be inclined to tell her when she turns, or when they think klaus died and caroline thinks she's about to die too because he's her sire. then caroline could feel that she has to tell her.
i hope this helps!
                                      
                                          
                                   
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