Stop looking at everyone else and look at yourself and your own life and what you think YOU need. Maybe say something to the shadchan that you feel she didn’t dress up enough and the shadchan could hint to the girl in a nice way if it matters that much to you. Look at the girls middos, talk about goals, aspirations, personality. Dont say no to a second date because of a silly thing like what kind of shoe she was wearing. This is your life. That is just my opinion. If you end up liking her, you can hint something like, “You know, you looked nice when you wore heels the other day.” If its right, she would want to make you happy. Hatzlacha.
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