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Here in Belfast (Ireland) the Smart car has been around for a few years - so let me tell you that it stops attracting attention from passer-bys very quickly.
I have to agree with a few other posters - the Honda Fit (or Jazz as it's called in Ireland and the UK) makes much more sense.
It comfortably seats five people (lots of head room both front and back); is cheaper that the Smart (here anyway); has an unfeasibly large trunk (the petrol tank sits under the front seats to add space); holds its value; and is a *Honda* - so will never, ever break down - unless we drive it off the Giant's Causeway...
We can park it easily anywhere in Belfast's tiny, narrow streets; and we can get 55 miles to the gallon from it with very careful driving (it has a mpg readout).
Ok, so that's Imperial Gallons - but that's still around 44 mpg US stylee.