Any recomandation of movies (especially from 1950-1995 period) with frendiship (romantic or not) between an boy and girl where the girl is older then the boy (and even taller! - I love girls above 5'9").

I do, too ! My wife is 5'11"... Knew a gal once who was 5'13"...She said that sounded better than sayin' she was 6' 1"...

Harold & Maude.
The Graduate.

Love That Boy. Local film. Don't know much of anything about it, I think it's a one-way attraction, boy wants girl.

I'm on the other end of the spectrum regarding height preference with women. The shorter the better, as long as they're not actual midgets, and have a small frame to match.

Once Bitten.. a vampire flick where a teenage boy is seduced by a rich vampiress in her late 20s.