Most black hats fulfill the minimum requirements for a sukkah, so if the girl thinks the guy might not be frum enough to wear a black hat on the date, she should bring one to the date to provide him with the opportunity to fulfill this mitzvah. The guy should bring cookies baked by his mother so that he can make a leishev, but she should MAKE the leishev because you obviously wouldn’t trust the bracha of a guy without a black hat. And he should wear heels for pirsumei nisah.
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