about the rain, i think that would be fun. i love when it rains, and i looove when it pours so i thinks thats not a problem. the frizzy hair is fine if you just put in some hair product brfore you leave. and if it starts raining after you left, its fine too noone will care.
about complienting girls, it might not be so appropriate on a first date but second and third i is definitley appreciated.