Originally posted by: Coalfax
Being its only a third date, do you really want to drain your wallet? It also depends on how old the two of you are to aid in where you may want to go ( level of well, pocketbook and sophistication actually ;-) )
If you have a somewhat bottomless pocket, (is ANYTHING in Boston reasonable?) you can try KingFish in Fanuel, which is a step or three above Legal. Then there is a great little French restaurant I hit in Cambridge during restaurant week a few months ago, Sandrines... but its pricey.
For some nifty ambience, not to mention some movie nostalgia, you can also try Grafton Street in Harvard Square. A little Good Will Hunting for ya.
Just some ideas, though I am going to guess that, like 95% of this board these days, you are under 27-30 so these may not all be options. Grafton Street may be your best bet of the three above.
Oh, for the record, Dating sucks. 🙂
Good Luck!