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Women wear flats on coffee dates and almost everywhere else (because cobblestone streets are hell on stilettos).
Unlike women in other major metropolitan areas, Boston chicks are typically more concerned with comfort and warmth than with fashion, so there better be a damn good reason to get dolled up.
Because Massholes are everywhere, parking means war, and we won't give up our hard-earned secret parking places to just anybody.
Not that any of these things have ever happened to me. Unlike in NYC and LA, the people you date will not have professional headshots on their online profiles.
In New York or elsewhere, a date can so often be a setup for failure; we are typically sitting down with a relative stranger working feverishly to put forward our most attractive, intelligent self, while at the same time scoping out the other person to see if they might be a fit…and to boot, we’re supposed to look casual and relaxed while doing it! Go volunteer at a soup kitchen or homeless shelter. Make a list of things that give you pleasure and find opportunities to go out and do them.