1 and 2 are fine, 3 looks like something she should wear to the gym, not a date
Anyway, I think he'll win over the crazy. Predictions for future plotlines: she gets another puppet and that makes him jealous, we find out she has a super sad and fucked up background, he starts growing closer with a (seemingly) normal girl and this starts to bother her internally but we find out the girl he's growing close to is a yandere or some shit.