I had the best idea. Other Sonic fans must brainstordie though, is definitely with Scrooge, while Rouge still can't decide between Shadow and Knuckles.(Sorry for all the theories/headcanons) Would probably steal tm with me.
Friendships:
Della and Tails; airplane nerds, Della would definitely try to be friends with him.
Della and Sonic; Personalities are very similar, A lot of the stuff I put for Dewey, both will be friends with Tails, I headcanon them both as having ADHD(Like me!)
Sonic and Dewey; Similar personalities, adventurous, put lots of effort into catchphrases, kinda egotistical sometimes, and blue color theme.
Rouge and Goldie; Thieves who flirt with people. Go steal things, try to double-cross each other, and fail(At the double-crossing, not the stealing)
Knuckles and Launchpad; Well, Boom Knuckles at least.
Enemies:
Scrooge vs. Knuckles; Would Scrooge not try to get the Master Emerald for the money bin?
Tails vs. Gyro; Not an outright thing, Tails is just very frustrated with his lack of safety with inventions and how mean he is.
Sonic vs. Magica; Because reasons. Also, she would make a good Storybook series villain.
If you have more ideas and storylines, please please please please please comment.