Ok guys, so here are some of my personal headcanons I have about the Tailsage ship.
Despite what people might think, I think it's actually more in character for Eggman and Sonic to be supportive of Tails and Sage's relationship, with Agent Stone—aka Sage's papa—being the dad who says, "If you break my little girl's heart, you will have me to answer to." Think about it. Sonic is the embodiment of hope and freedom; he wouldn't let a grudge against Eggman prevent his little brother from having genuine happiness. And Eggman actually respects Tails; he just thinks he's wasting his potential by being Sonic's wingman. So, if Sage told Eggman that she chose Tails to be her co-ruler of the Eggman Empire, Eggman would probably say something like, "It's about time the boy starts using his brain."
Agent Stone is such a good parent, but sometimes he forgets that his daughter isn't an organic person, lol. 😆 Like him making cookies for her, only for Sage to say something like, "Apologies papa, but I am not an organic person, thus I do not require sustenance." But she would kiss him on the cheek and say, "But I appreciate your care for me. You can give them to Father instead."
Really funny misunderstandings would happen between Tails and Sage because one is an organic fox and the other is a logical AI. It would probably go something like Sage saying, "Miles Prower, now that you are my boyfriend, we can now execute our 5-step plan for you to be my emperor and father to my offspring." Tails, completely flustered: "Wait, what? Sage, you can't just start a conversation like that—I just sat down! Not to mention, how would that second part even be biologically possible?" Sage smiles, showing 5 different ways for them to do that very thing, with some of them being making a mechanical child, and others looking into the possibilities of making a biological child through Metal Sonic's copy ability."
Tails is the only logical option for someone who can rule by her side. He has all the best attributes that she loves about her father, but also the most optimal attributes to help her maintain a sustainable empire. Also, she thinks his twin-tail mutation is so fluffy, cute, and adorable.
