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The Back Bay scene is pretty fratty so I would stay away from that. In that I would include financial district/Beacon Hill. People are pretty caught up in what they're doing so I don't think they're terribly open.
I think Somerville, Cambridge, and Jamaica Plain over by Stony Brook T stop are more eclectic, interesting scenes. Somerville (Davis Square) and JP will also be a bit for affordable. That would be my recommendation.
NYC and Palo Alto will be very different scenes. NYC is, well, NYC. Can't beat it. Boston is much smaller - more "quaint." Palo Alto is going to feel more suburban.
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