This list is highly subjective and personal, much much more nostalgic than informed. I haven't lived in the Boston area for more than ten years. (Search "Boston" for better current lists of people who live there now!) Anyway, here are the ones I love going to the most when I visit.
  1. East Coast Grill (Cambridge)
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    Wonderfully upbeat, casual, celebratory atmosphere. Fantastic menu specializing in seafood that is extremely high quality and still creative and fun. Full bar and great cocktails.
  2. Chau Chow City (Boston)
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    My favorite spot in Chinatown. I used to take the T there sometimes by myself and get an enormous lunch special and some tea and just think about things, and enjoy being a teenager in a somewhat seedy area.
  3. Bill's Pizzeria aka Bill's House of Pizza (Newton)
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    We grew up on this as the go-to spot when our Mom wanted a night off from cooking. It has only gotten better over the years, having added some really delicious and sophisticated options to their standards. Also served the best subs before there was Subway.
  4. Johnny's Luncheonette (Newton)
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    A relatively expensive 90s take on a cheap 50s diner, but whatever, Newton embraced it. Right location, right attitude, right name, right vibe, great food. Felt like the central spot in Newton Center and still does to me. @LevNovak grew up on it.
  5. The Helmand (Cambridge)
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    My parents took me here as a teenager and it blew me away. I've been a couple of times since. My family doesn't like "fancy" food, so this white-linen-tableclothed casual atmosphere was perfect for something celebratory. It's Afghan cuisine, which I haven't really seen since, and it is especially good for vegetarians.
  6. Sevan Bakery (Watertown)
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    A treasure that my dad introduced me to. Armenian and Mediterranean food to go. Incredible taste and selection.