[@TheWizardLizard] April miiiiight have seen Shizuka around probably once or twice - his white hair is hard to miss - but I don't think they would interact much at all since he's often flying to and fro US and the Asian countries during those 3-4 months of timeskip.

I'm not sure how their relationship would go, but depending on the situation and development in the IC, he might just try to maintain a professional front with her first because while they both share the similarity of valuing freedom, he lacks the idealistic view that most other agents have towards law enforcement - he is a realist.