Thank you all for the suggestions. I'm going to discuss with the boyfriend first, since I want to go to all these places and cant pick one!
So my boyfriend and I are celebrating our 5 year anniversary in a couple of weeks. I know there have been a lot of posts about romantic spots, but we're looking for something around $150 total for the two of us (including a glass of wine or so each) but we're willing to spend a little more if its worth it, unpretentious place, with solid, good food and really some soul, not just the newest trendy place. Cuisine preferences: anything other than Japanese/Chinese/Thai. Currently considering Blue Hill (too expensive?), Degustation (expensive but is it worth it?), Graffiti (does the shared seating kill privacy?) I havent been to any of these places yet, but they all seem to be very popular for this kind of occasion. Any other recommendations for something perhaps a bit more cozy?