To see a comedy movie!
Out to somewhere extremely fancy and expensive that he/she most likely cant afford in the first place!
Out to a nice play/musical!
Somewhere fancy like a mansion or an exotic area.
An apartment or a small house close to work.
Somewhere sunny,bright and far away from distractions.
Work in an office or something like it.
Be a caretaker/doctor/dentist/ect.....
Be a magician/theatrical artist/something creative and entertaining.
Somewhere sunny,and propose by singing it.
Somwhere quiet and music playing,and say it in poem form.
At a nice fancy restraunt,and propose by saying it the plain old-fashioned way.