In Sqaishey's Milestone Celebration song "Quack If You Wanna", Stampy makes a guest appearance and seems relatively nonchalant about Sqaishey time-travelling. However, due to the heavy implications that Feather Adventures takes place in a Shared Universe with the Lovely World, Stampy himself would have time-travelled as of that point in timenote Lovely World Episode 100, "Cat to the Future" took place in July 2013, while "Quack If You Wanna" chronologically takes place in June 2014, with present!Sqaishey travelling back from October 2014, and it is also likely that Stampy helped Sqaishey build the time machine.
Fridge Tear Jerker
Sqaishey's song "Jungle" takes place in February 2016, where they and Stampy explore the jungle near Feather Adventures, and the song itself is about confronting one's fears and facing challenges with bravery, optimism and support from friends. But when you look at the Lovely World timeline — once again, with the implications that the two series take place in a Shared Universe — the song would have taken place about a month after the HitTheTarget attack in the SLW episode "Evil Plan". Given Stampy's hesitation with charging into a horde of spiders with a wooden sword in the song... one would wonder if being teleported into a spider dungeon and going down to half a heart even when fighting with an Infinity +1 Sword left a mark on him. And then possible Fridge Brilliance hits — the challenges to face can include trauma.