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Where to take an older, hard-boiled, eccentric but loveable drinker?

My bachelor uncle is coming up from Manhattan. In a nutshell: The guy has lived in the same rent-controlled studio apartment for 40 years, is a huge packrat, smokes two packs a day, and is extremely eccentric and curmudgeonly (yet fun, with tons of great stories). He's coming up to Boston to meet a woman he met online (yes, this is 2011!) and we're meeting the night before for drinks and dinner.
The guy likes to drink. He's definitely an old-school bar type. I'd like to take him someplace for a few stiff cocktails and then a good steak dinner (he's not a very adventurous eater).
Any suggestions are welcome. He's staying in Cambridge, but I have a car and can pick him up and go wherever.

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  1. Davio's if you're looking for old school swanky steakhouse atmosphere. (Just be careful he doesn't fall asleep in the booth)

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    Davio's
    75 Arlington Street, Boston, MA 02116

    2 Replies
    1. re: barleywino

      Davios is pretty new school, actually.

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      Davio's
      75 Arlington Street, Boston, MA 02116

      1. re: C. Hamster

        I guess by old school I'm thinking lots of soft leather private booths , dark wood, dark room with soft lights...Davios seems to capture this sense of swanky privacy better than Grill 23 or Abe & Louies... maybe that counts as new school

    2. What a hoot! Is he more of a Frank's (NO Cambridge)/Jimmy's (Arlington...been there once..BIG pours and hearty old-fashioned food)/Chateau kinda guy? Or an Oak Bar/Locke Ober type?

      Curious to know where he's meeting up with his date?!

      1. I have to ask, what do you mean by "cocktails"? Some folks use this to mean "any alcoholic beverage", including beer, wine, and spirits or spirits-based mixed drinks of one kind or another. What does your uncle drink?

        http://mcslimjb.blogspot.com/

        1 Reply
        1. re: MC Slim JB

          From the description of the guy I took cocktails to mean drinks. Like a Scotch on the rocks. Prolly not angel share styleee.

        2. Take him to the Pour House for some boilermakers and then to Abe and Louies.

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          Pour House
          907 Boylston St Ste 21, Boston, MA 02115

          1 Reply
          1. re: C. Hamster

            I second the Abe and Louie's suggestion.

          2. Oh fantastic! MT Vernon in Somerville has your number. Good stiff drinks in a bar that still smells faintly of smoke and then onward to the dining room for basic but solid fare-- steaks pasta scrod and the like. Nothing that will knock your socks off but he'll be comfortable!

            2 Replies
            1. re: yumyum

              yeah, i think the mt. vernon/ franks/ gregs (watertown) is your vibe. possibly foleys in the south end. or doyles in j.p. after a few pops down the block at the drinking fountain or the midway cafe.....not that i have ever been thrown out of....er....i mean, into, any of these establishments.

              1. re: hyde

                I haven't been there (yet) but I've been told about how good the place is - was going to suggest Greg's in Watertown. You beat me to it, hyde.

                Also - what about Charlie's Kitchen in Harvard Square? Been years since I've been there (will NOT say how many yrs ago I frequented the place!).

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                Charlie's Kitchen
                10 Eliot St, Cambridge, MA 02138