stay at the motel 6 in brighton.
but yes its gona be winter. the cuty will be beautiful.
take her to harvard square, see some restaurants and some street performers, go to a comedy show,
take her to the north end, have a nice itlian dinner, and then go to mikes pastry (a must hit in the city)
take her to quincy market, check out the historic shit, maybe go shopping, then watch the snow fall.
take her to boston common, go to the frog pond go ice skating, another very popular bostonain tradition.
DO NOT GO TO ANY BAR MARKED CHEERS! these are shitty tourist traps