Super mega ultra headcanon for SH Tails and SH Amy.
I think Amy from Secret History was something of a mother figure for Tails. When Tails became Sonic's sidekick, he clearly had trouble connecting with the people around him, and Amy tried to help him with that, unconsciously becoming attached to him like a son. In Tails' case, he perceived Amy more as an enemy than a friend (remember the moment in the episode where he stole her hammer to rig it with a bomb), although his interactions with her were more cold than hostile. This is all because Tails didn't understand the concept of parenthood (the headcanon is that he was created in a SEGA lab and essentially has no parents 🥲), and all this care from SH Amy was foreign to him. Only after a long time, when he had already become a member of True Sonic's team and the others, did he realize that Amy from his dimension was like his own mother, but it was too late to fix anything.
