Shizune - blah, reminds me of few pests from high school, but without 'dere' side she has.
Lilly - I would stay reserved to her since such glamorous people more often than not hide well their evil antics. Y'know, sexually repressed and such.
Hanako - I'm quite a socialness nerd like her, but more of the stepford smiler type who doesn't care what THEY think about him, so either I would scare her off with too much straighforwardness or get full of her existential angst and pretty much tell her to go fuck herself, she'll feel better afterwards

Rin - platonic one. I can imagine sitting in some lone spot with her and playing 'who will get embarassed first'

Kenji - wouldn't mind him if he had more reliable personality. You can vomit now.