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Need a good place for a difficult conversation

I need to have a difficult conversation with someone and as trite as is sounds would like to do it some where public that will also "softens the blow" so speak. So nothing overtly romantic, overtly sports related and ideally nothing too impersonal (Cheesecake Factory and the like). Doesn't have to be a sit down restaurant per se but it should have good lighting and good food options. Excellnet cocktails a plus.

Cost is a non-issue, and ideally should be in Boston proper, South End and waterfront OK, North End would work too. Not looking to do JP, Brookline, Cambridge, etc

I live in the burbs these days and my treks in Boston usually end up in chinatown or "special occasion" places so feeling a little out of the loop on the day to day dining scene.

TIA

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  1. Perhaps the Bristol Lounge in the Four Seasons.

    1. Do this person (and yourself) a favor and pick somewhere they won't mind never going back to. Because it will instantly become "that place where foodieX2 dumped me."

      3 Replies
        1. re: foodieX2

          Even if youre not dumping them, they'll never go back

        2. re: misscucina

          The last time I sat at the bar at Rendezvous, there was a late-middle-aged couple sitting next to me negotiating their divorce. I felt bad for the guy; the woman was beating the crap out of him!

          I think Rendezvous is a serious-but-relaxed enough place for a difficult conversation.

        3. The lobby bar at the Taj? Went there a few years back (when it was still the Ritz) with a girlfriend who was having man troubles & needed to have a heart-to heart with a good friend. We sat on a comfy sofa, in front of the fireplace, while the waiter discreetly brought us wine & appetizers to nibble on. IMO, it's a good place to feel bad, if that makes sense.

          5 Replies
          1. re: gimlis1mum

            You know my first reaction was the old Ritz bar. I have not been since it became the Taj. Does it still have the same vibe? Thats exactly what we need- a place to have a good long talk about a difficult subject.

            1. re: foodieX2

              We did return there once after it became the Taj - that first night of "drowning" sorrows turned into a tradition of dinners out for just the two of us girls. We liked it just as much the second time, even got the couch seat again.

            2. re: gimlis1mum

              The idea of a waiter "discreetly" bringing appetizers immediately makes me want to watch an Aziz Ansari sketch about indescreet waiter service.

              "YO! LADIES! Who died up in HERE! DAAAAAMN! Let me slap those FROWNS offa those pretty FACES with some of my bitchin'-ass CRAB CAKES! This remoulade is like A SEX BOMB in your MOUTH, ka-BOOOOOM!"

              1. re: FinnFPM

                lol! I almost spit out my drink :-) I guess I should say, by "discreetly" I mean the waiter was sensitive to the mood on our couch. Not that I expect someone to read minds, but when we've been somber yet the waitstaff is insistently, almost compulsively cheerful, it's jarring.

                1. re: FinnFPM

                  If Aziz Ansari is around you should definitely order grapefruit soda.

              2. I'm a little confused. Are the excellent cocktails for you or the other person? If it's a tough conversation with downer news, the other person will probably not want to linger, and will probably lose his/her appetite.

                How about a coffee shop instead?

                5 Replies
                1. re: pinehurst

                  Coffee shop does not fit the the need for a place that's not too impersonal. I don't want to be at a Starbucks surrounded by people with their laptops. We are BOTH going to need the cocktails.

                  To clarify this is not a break up situation. It will be hard on both us. (family issue)

                  1. re: foodieX2

                    Roger that---I got that it wasn't a break up. I wasn't thinking Starbucks, I was thinking North End where one can be anonymous---not Mike's, obviously, but some of the old Caffe places fit the bill.

                    Since you'll be noshing and drinking during this conversation, choose somewhere that you feel at home--like the Taj. I wish you well with the conversation and its outcome.

                    1. re: pinehurst

                      What about a Caffe where you can grab a coffee, break the news, and then decide to get some drinks if the mood so warrants... Paradiso would be good for this.

                      What about a place like Stoddards?

                    2. re: foodieX2

                      You are coming out as a Yankee fan?

                      1. re: sal_acid

                        So OP should go somewhere nice for a glass of champagne to celebrate?

                        For the OP I would suggest a place near the Commons so that if you need a change of scenery/escape there is a quite place to walk around and discuss. When I hear bad news I always need to escape and walk around after.

                  2. If your difficult conversation gets a little loud, you'll get the attention of others at the Bristol and taj, including management.
                    Go over to the seaport hotel's tamo bar where if needed you can move into the lobby with your drinks.

                    1. Thanks to all who took the request seriously and with thoughtfulness. I truly appreciate it. I probably should have phrased it as sensitive subject even thought it is in fact a difficult one It is very unlikely it will get "loud" or that we will "embarrass" those around us.

                      Most likely we are going to the Taj or the Bristol as I like the suggestion of being able to go for a walk in the common afterwards.

                      Again- thank you for your suggestions.

                      4 Replies
                      1. re: foodieX2

                        Another good place is the bar in Beacon Hill Bistro- also right by the Common in case you need the walk Viperlush mentioned. The service is always great- the bartenders seem to read minds in terms of your mood- and there is also a fireplace and nice seating so that you aren't too crammed and, depending on time of the day, might have the right vibe. Good luck.

                        1. re: bmmommy

                          Other options: Oak Long Bar & Kitchen, the bar at the Artisan Bistro (I've had a few quiet convos there myself), and the Reserve champagne bar at the Langham. Good luck.

                          1. re: Swankalicious

                            off-hours at artisan aren't so bad, but i am not a fan of the renovation. however, the newish lobby bar at the ritz has small private seating areas, away from the bar which would be very nice for this sort of thing. goods luck.

                            the bar at the boston harbor hotel also has club chairs spread about in small groupings where 2 people could talk quietly and the service there is very professional.

                            beacon hill bistro bar is tiny. i can hear everything everybody is talking about at that place.

                            you could also go someplace like davio's and request a booth.

                          2. re: bmmommy

                            The bar at the Beacon Hill Bistro (one of my favorite places) is tiny and the Oak Long Bar is noisy and slammed most nights.

                            I'd vote for the Bristol. Quieter plus you can probably score a relatively private seating area.

                            GoodLuck!