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apushatayid
Participant

whatever you do, make sure you are both dressed for the activity. a nature walk in heels is probably not a good idea. a visit to an animal shelter in her finest shabbos clothing, also probably not a good idea. the rec center dressed like she is going to shul on shabbos, not a good idea. I dont know the rules these days, but when I was dating (almost 25 years ago) it was normal (actually, it was expected) for the young man to call the young lady prior to the date and make the arrangements for the date. I heard that isnt done nowadays, so I guess you will have to use a go between to discuss what to do and how to dress.