Boston is about two-three noches down.
1369 coffee is always full with semi-hipsters over educated types, and you can hear intersting conversations
Check out Davis sq. in Somerville, and especially Diesel Cafe. You see hackers there working with their laptops once and a while. The problem is that people are unfriendly, and if you just randomly start talking to somebody with their laptop open, they might snub you. Unfortunately it is not California. In here if you randomly start talking to somebody, they will talk kindly back to you, in the "who knows, something might come out" away. Over there they will talk back to you in the way "Why the frick you talking to me. Do I know you?". Big difference.
Finale-s in Harvard sq. has some really good desserts!
Harvard Cooop is my favorite bookstore ever. It has a certain "air", very inspiring place (like: you should be smarter, and try harder, kind of inspiration).
But here is my favorite activity while I lived there: Learn how to Sail in the charles river. In the boston's side of Charles river, at the beginning of the esplanade, there is the community Boat House. You pay something like 120$ per year, and you learn how to sail (all lessons are free), and you can go there and get a boat (you will start with small sail boats), or canoe out anytime you want. It is actually really fun, if you have the patience to learn. Since it is not even a real lake, and winds are not that strong, it is very easy to learn. And if you get good at it, it would be a great activity for a second date. Worth every penny.