Romance In Boston
 

I'm moving to Boston the beginning of next month and my certain someone will be joining me a few weeks after I arrive. Money is kinda tight, well very tight actually, so is there any like lookout points (preferably at night) where we could go? I'm really unfamiliar with the city so any suggestions would be greatly appreciated.

Castle Island
The Esplanade
You could pay $12 and take one of the ferries from the aquarium for a ride around to one of the islands/neighboring towns.
Enjoy! :)

Oh yes indeed. My favorite romantic spot (and the same for others, unfortunatately, but it doesn't metter much since it's so nice) is a little spot by the water next to the whale watch launch point. There's a giant compass rose made of stone on the ground and a lovely sea wall to sit on and watch the boats go by (and a good view of Logan across the bay). It's romantically dark at night and a little exploring of the area provides a lovely walk along the docks by the aquarium. I discovered it back in my college days when money was tight, but I still use it now as a nice place to quietly talk, but accompany it with a fantastic dinner at The Chart House (great seafood), which is right next to the spot I mentioned. Find The Chart House and you'll find the spot. It is a little hidden, but still downtown Boston.

An evening stroll around Beacon Hill will be sure to provide a romantic view overlooking Boston Common. The beautiful scenery, brick houses, and burning gaslights are certain to provide a lovely ambiance. (All free of charge, of course.)

Sometime, I recommend treating yourselves to "The Daily Catch," a delightful, small restaurant in North End.

Be careful not to fall in love with the city rather than your aquaintance. ;) It's a great place!

Thanks for all your suggestions, all really nice ideas. I'll only be there for a year, and then after that we'll be living together in the south. We’ll have a car so can venture out a little bit. It’s going to be the end of September first week of October so the leaves will probably be changing so a walk through the garden/common would be nice. He wants to do something by the water so I was hoping for like a cold windy day so we could walk arm and arm. I know whatever we do will be nice though.

With a car, another great thing to do is a walk on the beach at sunset. One of the better places to do this is Crane Beach in Ipswich, about 45 minutes to an hour from the city. You can follow up your beach walk with fried clams or a lobster roll from one of the many great clam shacks in Ipswich and Essex.

For a scenic overlook of the entire area, climb Great Blue Hill. Its about 10 miles south of downtown on the border between Milton and Canton. There is a small ski slope that faces northwest giving views all the way to New Hampshire. At the top there is a lookout tower that has a nearly 360 degree view of the area. There are several other hilltop vistas in the Blue Hills reservation, all are short (< 1 mile) walks. There is also a roadside lookout on Chickatawbut Road in the reservation. It has a beautiful view of downtown Boston and the harbour. Unfortunately for romance, the road is closed down at about 8 or 9 each night.
http://en.wikipedia.org/wiki/Blue_Hills_Reservation

Evening--does anyone have some suggestions that are a little more recent? Something that might be romantic, or something that would be good to do with a really close friend?

Boston's an old city. All the places named above still exist. ;)

Boston is a GREAT city for romance especially in the summer. It's got cooler temps! ^ Romance and hot weather---not good together. ;)

consider a walk around the reflecting pool at the Christian Science Center at night.

http://en.wikipedia.org/wiki/The_Fir...ist,_Scientist