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First date in the North End

Heading to the North End on Friday for a first date. We are both young professionals in our mid-late 20's. We were set up by a mutal friend, so we're still in the "getting to know each other" phase. Looking for a good first date spot, but nothing TOO romantic. And good italian, obviously.

I've searched the boards a little bit, but wanted some more suggestions.

Thanks.

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  1. Highly recommend La Galleria 33. Not the matchbox seating like some other Northend joints, very good food and a very nice atmosphere/decor. In the "getting to know you phase" it would be a perfect fit. Some other choices are very pricey and very "tight spaced' and a bit heady, which can make for awkward early dating. There's a lot of pressure when the menu prices are high and one or both parties feel guilty about ordering. La Galleria 33 is a perfect fit.

    1. Any idea how adventurous your date is? Any allergies? Regional preferences? I tend to favor Northern and Central Italian over the Southern-inspired Italian-American served at most North End places, but that's hardly everyone's preference.

      1. Ricardo's on North Street is a fairly roomy, comfortable place with good Italian food, and it's rarely crowded, so you probably won't be struggling to hear each other talk. And while it is a little romantic, it's not as cozy and intimate as, say, the basement dining room at Assaggio on Prince Street.

        1 Reply
        1. re: hiddenboston

          Ricardo's isn't a half bad room, but I didn't like the food there.

        2. How about a walk-about first date?
          Start at Neptune Oyster - grab a few oysters at the bar there with a cocktail. Bailout opportunity #1 if it's going poorly.
          Things going well? Walk down to Pizzeria Regina and grab a pie (or a slice? Do they sell slices there? I don't think so....but if they do, all the better.) Or try Monica's on the corner of Prince and Salem. Bailout opportunity #2.
          Conversation still flowing? Go around to Cafe Victtoria or similar for cappucchino, pastries, etc.
          Walking and talking takes a little pressure off, no?

          3 Replies
          1. re: Bob Dobalina

            That's a great idea. Love all the opportunities for bailing, and of course strolling.

            1. re: Bob Dobalina

              Hey Bob,
              That's an excellent itinerary, even if you don't want the bailout option! My wife and I love all 3 of them and together, with a walk, is a perfect date. My preference is pizza at Regina's tiny bar with a glass of cheap red!

              1. re: Bob Dobalina

                First rate itinerary, Bob Dob. No slices at the original Regina, so it would have to be a whole pie.

              2. Try Maurizio's. The food is wonderful, it's small and cozy, and the chef/owner is always there. If you can, try to get a reservation as it gets very crowded on the weekends. Our Italian-born friend eats here almost exclusively, and he knows his food.

                2 Replies
                1. re: mcupcake

                  A second vote for Maurizio's or, if you can get the table by the windows upstairs at either Marco or Taranta - which both have great food, it would addd to the first date vibe.

                  1. re: Northender

                    Will second all of Northender's suggestions and toss out a third on Maurizio's. Carmen and Euno would also be good, as balleresq suggested below. Another possibility is Davide, which has warmly evocative basement level digs and good food.