You're welcome!
Leo: The order changes based on what's already unlocked, so I'll tell you both. For both CGs, get completely drunk by accepting & drinking everything offered. There's one CG for reaching out for him and another CG for letting him pass by.
Matt: Go hang out with Matt after Will's class in the afternoon (Text someone > Matt). During that hangout, proposition him without trying to play it off. This will add an additional CG for the evening hangout after you nudge his knee.