Things that Jude does canonically/often repeatedly throughout events or routes that make my heart go *high pitched screeching*
Jude likes MC's bedhair/fixes it (even tells her not to show it to others in his "A day with Jude" event)
Jude gazes at MC longingly/lovingly when she's not looking
Him being silent when he is enjoying MC's company/silently being affectionate towards her (when he's holding her hand or gazing at her). He likes bullying and teasing MC but there are so many instances where he just quietly loves MC AND IT'S SO SWEET (thinking when he listens to MC singing happy birthday to him in his BDAY story sale too)
He likes being kissed on the forehead (ABSOLUTE SCREAMING!! MY HEART!!!) For this one I'm 100% sure he sees it as THE gesture of love, especially knowing his reaction in his event versus Nica (when MC kisses him on the forehead) and when he does it to MC in the Ghost Report event
Jude admitting -though only to himself - that if anything were to happen to MC (especially her dying) he would be affected DESPITE not being in love with her at this stage. This one is especially dear to me T_T there are so many moments (First-class ticket event, Bond story Love Tactics, Final assessment event) where he's repulsed at the idea of MC dying (his quote "Can't have ya dyin' on my watch. Wouldn't be able t'sleep.")
How he treats kids. This one is obvious since Jude is repeatedly shown as gentle with kids but the FUNNIEST thing I've noticed is when he uses his ability, because he only needs to touch someone's forehead to put them to sleep and throughout events and characters routes, he gently taps on children's forehead but smacks the ever loving shit out of people he hates when he uses his power and that had me wheezing so hard