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Gay in Cleveland, Ohio, United States
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If you're not in grad school, the person asking may pause, give a puzzled look, and contemplate their own crippling student debt before continuing the conversation. Just resign yourself to talking about your education every time you go out. I could try to explain why this is, but I would just be making stuff up. Or the Celtics or Bruins, for that matter.
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.
The notable exception to this is Back Bay, where ladies wear lipstick and Lulus to walk their dogs from one end of Newbury St to the other. If it's not on Gcal, it's not a date Outside of Silicon Valley, Boston is one of the biggest tech cities in the country, so everybody has 9, different apps to manage their social lives.
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Observing OkCupid dates in the wild is practically a Cambridge-side spectator sport. Head to Kendall Square for the best seats. Accept the inevitability of dating people who spend more time with their MacBooks than their fellow humans, send unsolicited and inaccurate erotic fiction via text message after your first outing together, break out a backgammon board in the middle of a bar but refuse to teach you how to play, or demonstrate how many push-ups they can do approximately five in the middle of a crowded Chipotle, while confused onlookers hesitantly order burritos.
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Not that any of these things have ever happened to me.