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Night Out restaurant that won't leave me sobbing into my overpriced steak

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My boyfriend's birthday is this week, and we had originally planned on going with a splurge at Ruth's Chris. It doesn't seem to be worth the pricetag, however, so now I'm looking for backup. What do you think for downtown/south end, around $150 for two, and classy enough to be a definite Special Occasion? For instance, although I'd love to try Troquet I think it'd be too expensive, and Franklin Cafe might not be fancypants enough. I'm thinking Grotto, but any other suggestions? Thank you!

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  1. Metropolis Cafe. Intimate, romantic space, great food.

    I like:

    Grilled calamari salad
    Mussels in garlic, red pepper, and basil broth (one of the best I've had)
    Hanger steak with bordelaise and roasted potatoes
    Everything else

    Entrees top out at about $21

    1. Don't be mislead by Troquet's image. You can eat well there and not break the bank. Ask Chris to recommend something within your price range for wine. You can't miss him, he's the guy who looks like the bouncer. But, hey again image is misleading because he's a great guy and he'll accomodate your budget.

      1. our dinner at grotto- see my long post of a few days ago- was just superbly satisfying. a lovely spot and def'ly doable w that budget. the villa caffagio chianti is a good wine pick.

        1. I had dinner at Metropolis this weekend and was going to suggest that. My friend and I split a 1/2 bottle of Duval Leroy rose champagne (YUM). We also shared the beet salad which I thought was just delicious. I ordered the bucatini carbonara which I thought was very good though it was REALLY creamy so I'm thinking there must have been heavy cream in their sauce (when I make it, I just use eggs and cheese). My friend had the hangar steak with whipped potatoes which I tried and thought was very good. All of the entrees are in the $20 range. We got out of there at about $50 pp all inclusive (+ another glass of wine each).

          1. I had a steak once at Metropolis that was fantastic, so he can still get that if necessary. But, I don't know if that room is "Special Occasion" enough. It is quaint, to be sure, but I don't know if I'd call it "romantic". Actually, although different, I would rank Franklin as having a more "special" vibe and atmosphere.

            I think Union might have more of that "special occasion" feel. Definitely a nice room. And it should be within the price limit, depending on what wine/booze you order.

            1. I've always felt that "Special Occasion" restaurants were different than "regular night out" restaurant. So I probably would not go to Franklin Cafe, even though I love the place. I'd also weigh atmosphere more strongly than usual.

              Downtown: Les Zygmoates in the Leather District (especially if you like wine), Spire, Meritage (in the Boston Harbor Hotel)

              South End: Aquitaine, Sibling Rivalry, Hammersley's, 28 Degrees, Union

              I wouldn't put all of the restaurants on a "best food" list by any means.

              1. Thank you all so much for the great suggestions! After extensive board research and waffling, I've decided to go for more of a fun date night out than a fancy occasion. Franklin it is!