Well Cloudy isn't that much of a Talker too sooo Step 1 Jude and Cloudy would get along well might even have their own language via stares , but For Fio he'd sweat bullets it's not that he is shy or anything, but he is too good at reading face expressions and Being Around Fio would get him pretty confused on what to do next
Flora would keep showing cool Stuff To Jude to Break the Ice Between them Because she is just chill like that As for Fiora she will have that Spider-Man Pointing At eachother moment because their Names are One letter away from eachother, But she'd be fond of her because of her Passion for her friends and In Flora's book there is nothing cooler than A True Friend
Leaf (My dear Aurelia) would be Wary of Jude at first Since she gets Frightened easily but eventually she'd warm up to him and I say they'd Make a pretty solid Duo by Hiding behind people together
Fio on the Other Hand would Get Aurelia to the Verge of Tears, someone looking at her that coldly would get her pretty devastated and Scared but if they Got Closer I can See her Spending most her time Glued to Fiora
Luciel, whew that Boy despite how sweet he is when People aren't around Wouldn't get along with Neither Jude nor Fio, For Jude he'd think he doesn't wanna talk to him or is purposely Ignoring him As for Fio you can guess what he'd take offence to.