Most Helpful Girl
Somewhere quiet enough to talk - so not a very loud bar.
A little bit romantic like a rooftop bar or garden would be nice.
Somewhere to get a drink can be good to ease into it, but don't make it the entire date.
Girls care about how they look and will probably dress up, so if it's windy/cold out they'd be cold in their dress, and they probably don't want to hike around in heels.
Somewhere I haven't been before would be exciting - your favorite spot is a bit more personal and a turn on.
Standard movie gets a bit boring.