im a lil late to the party, but a while back i came up with Mami Tomoe (from madoka magica) X Kanaya Maryam (from homestuck) (*^_^*)
i think both of them being the "mom friend/caregiver" type, who both seem to wish they could have more normal experiences being teenagers in really messy life circumstances, would be drawn to eachother from a place of empathy for the others situation
i also really like Kris (from deltarune) X Dave Strider (from homestuck), theres this one artist on twitter who draws/drew a lot of ship art of them that i ADORE (@chris0001110 if anyone wants the acc)