Hello, Gerry and Michael (Shelley) probably never met in canon as Gerry started working with Gertrude in 2013, and Michael died/became the Distortion at some point before 2011
Also! (because who cares about canon) They're a popular ship and their ship name is DoorKeay!
I love my dead gay sons
I was already tempted to ship them because opposing aesthetics and a mutual hatred of Gertrude
but then they were both dead and I'm sad and if drawing fanart of my dead sons in a meadow talking about how much they hate Gertrude is what I need to not be sad then drawing I will go
To be fair impossible ships aren't even a first for me in this fandom, within a few days I had decided that Joshua Gillespie from MAG 2 (Guy who gave no shits about an empty coffin he just... Got one day) and Nathaniel Thorp from MAG 29 (Guy who cheated death and became immortal and also is illiterate) would make a lovely couple
I have yet to draw fanart of them but I will, all of them
Edit: Note, Nathaniel and Joshua's ship name is ImmortalCoffin in my mind since I literally just came up with it by myself