[kenberman]

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OP- Which city?

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Cambridge/Somerville (Boston, basically).

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what neighborhoods

one is bound to be cooler than the other.

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Inman Square vs Alewife, which isn't really a neighborhood at all

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I say take her to Back Bay. Dunno if Boston isn't an option for some reason, but it's neutral and fun.

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Back Bay is a good option. the only negative is logistics. driving/valeting is kind of a pain, and taking the T on a first date is kind of ghetto I think. a cab is an option, I guess.

basically, I think I want to avoid driving or public transportation. I don't drink and drive (if I'm over the legal Blood Alcohol Level, I won't drive) but I want drinks to be part of the evenings itinerary.