7. Walk the Boston Harbor
The Boston Harborwalk offers a free, downloadable audio tour that will take you along the water and scenic areas downtown. Follow along with your date, or smartly do it a few days in advance and impress her with your extensive knowledge of the Hub's seafaring history. There are also a handful of pay-what-you-like walking tours available from Free Tours by Foot that cover various neighborhoods around town.
8. See Shakespeare on the Common
Each year since 1996, the Commonwealth Shakespeare Company has presented full Shakespeare plays completely free of charge at Parkman Bandstand. Grab a blanket, a couple of burgers from jm Curley, and a Thermos filled with "water," and enjoy the show.
9. Go to a burlesque show
You might think of striptease as an outdated and slightly skeevy form of entertainment, but in Boston, that’s far from true. The city’s many burlesque troupes (including several nationally recognized groups like Rogue Burlesque, Sirlesque, and The Lipstick Criminals) have amped up the art form to include some of the East Coast’s best comedians, dancers, and variety artists. For less than $20 a ticket, you can see some talented performers rock out with their... you get the idea.