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Casual night out suggestions

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My wife and I celebrate our anniversary every year with another couple that shares same anniversary. We typically take a trip each year, but are staying local this year due to both wives expecting. Open to anywhere in Boston/Cambridge/Somerville, but would like to stick with one neighborhood where we can do pre-dinner drink (for the guys) / dinner / dessert. Also trying to keep things very casual this year. My first thought was Inman Square - Bukowski or Druid for a pre-dinner beer, East Coast Grill for dinner, and Christina's / Toscanini for ice cream afterwards (gone are the days of going out drinking afterwards, at least this year!) Any other suggestions in terms of neighborhood and combination of casual bar/restaurant/dessert place? Thanks!

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East Coast Grill and Raw Bar
1271 Cambridge St, Cambridge, MA 02139

Bukowski's
1281 Cambridge St, Cambridge, MA 02139

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  1. Your idea above is certainly a fine one but I guess I would suggest Oleana, with its tremendous and unusual food and its lovely patio(not reservable). You could meet for drinks, early, so you get a patio table, and then the wives could arrive for dinner. Dessert could be there or at Toscanini. You won't have to yell to be heard or be in the middle of the craziness of ECG. And pricing is pretty equal between the 2 places.
    oleana:
    http://chowhound.chow.com/topics/790043
    beers ist:
    http://www.oleanarestaurant.com/wine-...

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    Oleana
    134 Hampshire St., Cambridge, MA 02139

    2 Replies
    1. re: opinionatedchef

      If you go the Oleana route I would suggest Lord Hobo down the street for your pre-dinner drinks especially if you are interested in beer.

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      Oleana
      134 Hampshire St., Cambridge, MA 02139

      Lord Hobo
      92 Hampshire St, Cambridge, MA 02141

      1. re: mocooks

        LH has a full bar, and from what I recall reading, good cocktails too. I can tell you first-hand though that the beer list is great.