It’s not covering up who you are. At that stage in my life I was also a “Denim Girl.” I even wore my biz to Touro (gasp!). But on a date it is simply not apporpriate. You should be dressed better than that. You should be wearing shabbos clothes, not weekday clothes! Unless of course its like date #5,6 during the day and planned as casual eg. museum, boat ride, park, etc.
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