Dear Annie

  4.0 – 306 reviews   • Wine bar

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Dear Annie 02140

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DEAR ANNIE

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Dear Annie. 1741 Massachusetts Ave. Cambridge, MA 02140. Get Directions +1 617-571-1885 https://www.dearanniebar.com/. Discover Dear Annie & More. Guides · The …

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️ natural wine + organic fare kitchen ’til 10 tues-sat | 9 sun-mon queer, woman + nb operated sibs @rebelrebelsomerville @wildchildsomerville …

Reviews

Lockie Hunter
Dear Annie is exquisite! This is the best grilled cheese I’ve ever had in my entire life, which was surprising because it’s a wine bar. And the wine…! Read on for a very detailed review.

I don’t believe I have seen a better collection of wine by the bottle anywhere! And it was so eclectic. The focus on natural wines really brings wines to the table, literally, that I had never seen before. And the sommelier/server at the bar was incredibly knowledgeable and found a bottle for me that suited my palate. I lived in San Francisco for a decade and so I really know my California Reds, and we just spent some time in Mendoza in Argentina, where I received quite an education on Malbecs. This was not that menu. They had varietals I had never heard of.
Now… Let’s talk about that grilled cheese. The oysters were very good. They were nice and clean and it was happy hour and so they were half price. Great standard oysters. But the grilled cheese! Oh my! I could not imagine anything better to pair with the bottle of red than this grilled cheese. We paired the oysters with a white, but when it came to the red, we really wanted something different. I ordered the corn soup to dip it in, and it was enough of a small portion that both my husband and I have plenty to dip. After all, the corn soup was not main attraction. It was the grilled cheese. I make my own grilled cheese at home, and I include a lot of cheeses including Brie and goat cheese. This one rivals mine at home; there was something about the soft yet crunchy bread that made this an absolutely perfect grilled cheese. Do you remember the movie ‘chef’? It’s that type of grilled cheese. Perfection. I would come back again for the grilled cheese and a glass of red wine, and I don’t live anywhere near Cambridge. Honestly, I would come here as a destination wine bar/grilled cheese place. Don’t ever take the grilled cheese off the menu!
As to atmosphere, it was just what I had hoped when I walked by one day. Soft lighting, nice big communal table, but also two-tops and three-tops scattered throughout. On the communal table there were a lot of large dried arrangements so you did not overhear the conversation of the people across from you if you did not wish to. The experience was a delight from start to finish.
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Jes Maxfield
My favorite local! Fab wine selection, immaculate vibes and welcoming place to be. The communal table and nooks are (especially in the evenings) such a cozy spot, perfect for an intimate date or catch up with good friends. The owner and staff are very involved and invested in the community which is a refreshing and needed change.

Go and order a refreshing glass of bubbles, onion dips and chips (trust me) and anything else on their rotating menu and you’ll have the best night out you’ve had in a while. We love you, Dear Annie!!
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Megan Rausch
Dear Annie is a STAPLE. This was the first place I came when I moved here 3 years ago. I immediately felt at home. Now whenever people need a recommendation I was always suggest Dear Annie. The wine, aesthetic, people… top notch.
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Amy Larson
come for the delicious wine, stay for the music, vibes and food. then come back for the wine and bring friends. repeat. again and again, Dear Annie delights!!!
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Josh Cole
Hands-down one of the best wine bars in the Boston area. Incredible natural wine selection, super knowledgeable and friendly staff who won’t make you feel silly for asking questions, and the food (those tomato biscuits!!) is next-level delicious. Warm, cozy, and welcoming. Exactly the kind of neighborhood spot every city needs more of.
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Emma Giangregorio
I have been dining at Dear Annie for ~3 years and it’s by far, my number 1 recommendation for anyone visiting the Boston-area. The staff are incredibly kind and detail-oriented, menu is always thoughtful w local additions and includes variety of options. The wine is just next level too, they really know what they’re doing. Ambiance, there’s nowhere better. I have been there on a dinner date, with family or friends. My favorite spot is a corner at the far end of the community table, by the wines. Only SOME fav dishes, the oysters ALWAYS, pickled veg and cheese plate, grilled cheese, seadog is insane, any ceviche or crudo, onion dip. I also have a sesame seed allergy and they have accommodated me in many ways, at one time making me a completely off the menu crudo. Genuinely always leaving this place with a lovely experience.
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Danielle Prudholme
Extremely uncomfortable seating. We reserved a dinner table but were hunched over a low drinks table from hard plastic folding chairs.

The space has no sound controls and gets extremely loud which makes it difficult to converse.

The food was lackluster. We had been excited about the grilled cheese and found it just didn’t deliver. Also, the salad was mostly parley and cost $17.

Servers at the desk were nice but won’t return here without some major changes to the space/menu.
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Bridget Kiley
We love Dear Annie! The wine selection is amazing, we’ve never had a bad bite or sip. Shoutout to the onion dip and potato chips that we get every time. We’ve even hosted a private event here (the dear Annie staff was amazing) – it was our favorite gathering to date
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J. Roberto Garcia
I understand the poor reviews; however, they miss the point. Dear Annie is very informal and caters to a local quintessential crowd: looking for a tapas alternative and good wine. The wine is good, I disagree with others who think otherwise. Having said that Dear Annie should take note of reviews and pivot a bit to cater to a greater crowd. I also think it was delicious.
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Jeannette M
I didn’t read the reviews before I went, but I, too, was appalled at the 23% gratuity. I don’t mind paying a tip when there is actual service. But, my date and I entered, sat down (on uncomfortable stools), were handed menus and told that we needed to go up to the counter to order our drinks. We walked up to the counter, they poured the wine, put the glasses on the counter, and we had to carry our drinks back to the table. What exactly was the service we were paying for? 23% is high for a tip anyway unless there is great service. I liked the ambiance (though not the uncomfortable chairs), but definitely won’t be going back due to the unexplained gratuity.
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