when shipping characters i tend to look into the characters themselves and see if there's any sort of thematic parallels or any other interesting literary sort of "vehicles" of development that could either develop each and both characters or illustrate a side of them that could reasonably exist but isn't shown otherwise.

unless i'm making a OC with my girlfriend, then it's just shameless bias for my S/O sorry not sorry fellas

Mostly the possibility of good back and forth between said characters. If you feel more can be squeezed out of their dynamic that's the kind of stuff that motivates me to ship.

When it comes to OCs, another factor is what new possibilities or paths do said shipping open to my OC. IT's why I tend to like when I get to ship characters with friend's OCs cause it opens the doors for brainstorming and back-and-forth of ideas.

First off I think about whether the characters/OCs look good together. Then I consider how their personalities compliment or contrast one another. If I think they could realistically work out then I become invested! I really like when characters actually feel like they’d canonically work out. I think it’s nice when characters look good with each other, but it’s more important to me that they actually make sense.

it depends on if i'm emotionally attached to both characters JDJHDJSH honestly both mono and poly ships are fine as long as i like the characters in the ship and can get behind them + brainstorm. the more i develop them, the farther i sink and my enjoyment grows with time!

It has to be with someone who is equally invested with their character as I am IF it’s single ship. I usually prefer single ship pairings as it’s easier for me to manage and I feel like I’m able to develop them more.
I’ve shipped characters where my shipping partner either completely skips on the character or forgets about them entirely and it’s not as fun that way.
I’m also not the biggest fan when a ship is… purely NSFW, I don’t mind NSFW at all because I’m an adult but if that’s the entire foundation of the ship I’m not interested.

When it comes to multiship I'm usually selective ! But I lessen up on rules quite a bit ♡

I mostly only ship w one person (bc i'm too much of a wuss to talk to anyone else abt oc dynamics at all even friendships sfsdgd) but generally if i see a character i like i ask nicely and make my own oc, or he'll do the same, and if we happen to make 2 characters that happen to match up well? cool ship. But for the most part i think its me seeing and going "hey marriage??". I get invested just from talking abt them, bc its hard to make a character who i really dislike, and we just kinda vibe and i get lowkey obsessed for like a week to a month in which the ocs develop rapidly and then i get attatched and u kno,,,

I think the most important think for a ship is that all members involved feel like their own distinct character. That they could very well stand on their own outside the ship, but the ship just elevates them even more. The ship can compensate for their bad traits and or amplify their good ones, but it's crucial the character has those traits to begin with.

For me, I like picturing characters I'm shipping learning more about each other.

Be it big pieces of backstory or tiny little quirks, I get super into imagining the dynamic shifting and growing more outward and multi-faceted as these people paint a more complete picture of the other: learning what makes the other tick and how that in turn can become part of how they themselves tick

With OCs, I rather ship with friends that I talk to a lot!!

AS FOR CANON DOE...I am just basic, if they get along and seem cute together then MAYBE I'll ship!!
Also my all time favorite shipping trope is opposites attract SO LIKE IF A PAIR IS LIKE THAT YOU KNOW IM LIVING FOR ITTT

I’m cheesy and usually like the canon couple that’s in the show. But otherwise it’s usually the two character that get me all cheesy and happy when they’re together.

For me, it's if the two characters in question have a nice natural flow in terms of how they act and speak with one another. Starting from there, and seeing where it goes.
:)