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

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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

            2. If Harvey Pekar (God rest his soul) visited me in Cambridge, we would go to Casablanca, People's Republik, Cantab Lounge, and the Druid, then perhaps Atwood's for some music.

              7 Replies
              1. re: hckybg

                Gotta take him out for Jazz music though ;)

                1. re: Trumpetguy

                  And no yuppies!!

                  1. re: hckybg

                    He was a great guy--I spoke to him on the phone a few times :)

                2. re: hckybg

                  Long story short, I had the privilege of having Harvey Pekar take me on his own highly idiosyncratic tour of Cleveland in 1993. The itinerary included a yard sale (Harvey was on the lookout for LPs he could possibly resell), lunch at a middle eastern restaurant in the public market, a bookstore warehouse, the cemetery where James A. Garfield is buried and dinner in an eastern european restaurant (might have been Hungarian). I don't think Harvey was into any kind of bar scene at all. But a jazz club, yes, especially if they had someone playing far out stuff. A third stream concert at New England Conservatory or Berklee would have been right up his alley. As far as food, what he wanted was a combination of tasty and cheap. He'd have been happier at, say, the Greek Corner in Cambridge than at Oleana. The bars you mention would be on Harvey's wavelength if he was a drinker, but I don't think booze was one of his interests.

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                  Greek Corner Restaurant
                  2366 Massachusetts Ave, Cambridge, MA 02140

                  Oleana
                  134 Hampshire St., Cambridge, MA 02139

                  1. re: katzzz

                    Awesome!

                    1. re: Trumpetguy

                      Great story, and lucky for both of you to have met him. I can certainly believe he was not a bar guy, though his portrait popped into my head as the OP described the eccentric, packrat, curmudgeonly, story-telling uncle on his way to meet a distant love. I was just walking past the Lily Pad in Inman, and a jazz quintet (or so) was going absolutely crazy--definitely Harvey territory.

                      1. re: hckybg

                        You nailed it. Harvey would have loved the Lily Pad.

                3. hi,

                  how about the Taj or the 4 Seasons? The Taj really feels old school to me.

                  In Cambridge, Rialto or Craigie might hit the spot.

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                  4 Seasons Restaurant
                  361 Reservoir Ave, Providence, RI 02907

                  10 Replies
                  1. re: cambridgedoctpr

                    Nice places, but too fancy! He's an old East Village guy, in a new East Village kinda world. Gotta find a dive bar, not a power brokering spot. :)

                    1. re: hckybg

                      Should you take him to Wally's then? Followed by steak dinner....?

                      1. re: hckybg

                        East Coast Grill - great food, good booze, never too fancy.

                        1. re: teezeetoo

                          ECG not very old school ....

                          1. re: C. Hamster

                            really? it's very east village to me and would fit in comfortably there. probably be a sensation in fact, particularly hell nights.

                            1. re: teezeetoo

                              ECG does not feel old school nor East Village to me. Great place to eat &/or drink though ;)

                              1. re: teezeetoo

                                Are you talking about East Coast Grill or Green Street?

                                Because ESG's bright colors and hula skirts doesn't speak of East Village or old school.

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                                Green Street
                                280 Green St, Cambridge, MA 02139

                                East Coast Restaurant
                                1456 Dorchester Ave, Dorchester, MA 02122

                          2. re: hckybg

                            yeah, fancy and old school Boston Brahmin; worth seeing once. It has not changed since i have been in Boston.

                            1. re: hckybg

                              Cantab. Or Middle East. Both will have people his age, plus a whole kaleidoscope of others.

                              I know you said steak, but if you were going Italian, I'm feeling the Hacienda on this one.

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                              Middle East Restaurant
                              472 Massachusetts Ave, Cambridge, MA 02139

                              1. re: dulce de leche

                                Yeah! The Cantab - both SO and I thought the same thing.

                          3. Frank's in North Cambridge or the Mount Vernon in Somerville if you're less concerned with the quality of the food. Both are old-school and neither is remotely upscale.

                            For drinks, I'd also suggest the Cantab.

                            1. Probably not too convenient but the Pleasant Cafe in Roslindale might fit the bill.

                              8 Replies
                              1. re: Pegmeister

                                Good call Pegmeister -- that's totally in the same wavelength as the Mt Vernon, Frank's, etc.

                                In fact, I went in on Friday night and had the prime rib ($15!) and friends enjoyed the chicken / eggplant parm, the swordfish kabobs, and wings. I really love the place, based on two visits and it feels preserved in amber in the best way.

                                1. re: yumyum

                                  Don't forget to try Pleasant's pizza too....one of the best pies on that side of the city!

                                  1. re: Science Chick

                                    It looked FANTASTIC!!!

                                    Friends of mine live around the corner and I'm hoping I can persuade them to go to the Plez more often. If not, I might "pre-eat" there in case it's pasta and nugget night again for the kids.

                                    1. re: yumyum

                                      Thank you to everybody. I think we'll be drinking at the Cantab and then heading to Abe and Louie's for a steak dinner. He's meeting his new "paramour" at 75 Chestnut (?).

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                                      75 Chestnut
                                      75 Chestnut Street, Boston, MA 02114

                                      1. re: Swankalicious

                                        That sounds like a great plan. Too bad Forest Cafe is now defunct. That would've been a perfect place to take him....Now that I think of it, maybe Plough and Stars would be a good place to take him pre-dinner? Where is Peter O'Malley drinking these days since Forest Cafe closed? That guy is a trip....

                                        75 Chestnut definitely attracts both the old- and new-ly pickled Brahmin crowd, at least when I was there last.

                                        1. re: digga

                                          This will probably get understandably deleted by the mods, but here's an interesting article....History of Ploughshares (and a little about Plough and Stars thrown in for good measure).

                                          http://thephoenix.com/Boston/news/129...

                                          To keep it on topic, I AM curious to hear where you took your uncle, how the date was, etc....

                                        2. re: Swankalicious

                                          Have a great time, Cantab is a lot of fun. I'm not sure when the music starts, but there's always something good or entertaining (except last time I was there on a Thursday, and it was taken over by BC kids playing Britney Spears between sets of the Chicken Slacks--not cool). As my buddy always says, every kind of person in Cambridge is there and they are all dancing with each other (or sitting at the bar with each other).

                                    2. re: yumyum

                                      The inside has excellent patina!

                                  2. I would suggest Wally's if you want something old school in an east village kind of way. Definitely got that vibe, plus the music is always good.

                                    1 Reply
                                    1. re: Wannabfoode

                                      Thank ye for the recommendations, loyal Hounds. Uncle breezed into town and we ended up foaming our cups at Trina's Starlight Lounge, of all places. We then shimmied down the street to the East Coast Grill. Both venues seemed to suit him, although I've never eaten a meal that I've loved at ECG -- somehow always manage to order "wrong." Nonetheless, uncle liked the vibe of the neighborhood. We had hoped for Cantab but his date lives near Inman, as it turns out, so it was to Inman we went.

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                                      East Coast Restaurant
                                      1456 Dorchester Ave, Dorchester, MA 02122