Such a cute place and the staff are so knowledgeable. I don’t know much about wine but with a simple conversation about what I like they are always able to help me find something I love that’s also new and exciting.
The food is also delicious. Simple but well balanced and the salads are out of this world. The cod and whatever bean dish they are serving at the time are my other go-tos.
Madison Jozefiak
Cute and casual-looking place, but don't be fooled. It is exclusively for wealthy regulars and wine snobs. The servers are extremely rude if you don't fit in those categories. They'll give you disgusted looks for asking basic questions about their confusing menu and then stick you with an ALREADY INCLUDED 23% tip. They made me feel so uncomfortable, it was such a bad experience. Never going back.
Noah Berman
This restaurant/wine bar was great when they first opened and has gone downhill ever since. I keep wanting to give it another try but after my last experience I’ve given up. Will not be going here ever again.
Pat Tomaino
I was in here on a Sunday evening when a huge (and beautiful) display of foraged flowers fell over on the great table, and people were pros about it 👍🏽
Ruthney Benjamin
Dear Annie is a cozy natural wine bar with a chill neighborhood feel. The wine selection is unique & carefully curated, the staff are knowledgeable, & the food delish.. grilled cheese, deviled eggs, & onion dip are all banging .. the 20% tip is, & has always been, standard in this industry so I don’t understand the hate there + 3% goes to the kitchen & that does not bother me in the slightest, as it’s very common on menus across the country these days. Please don’t go there expecting a red carpet to be rolled out in front of you (the entitlement in some of these reviews is real!) .. anyway drink natty!
Molly Calkins
Went to Dear Annie on a Thursday, 8:30pm with two friends. When ordering, we sent one group member to bar, and he was basically asked if he could afford what he ordered. We were all dressed well, groomed neatly — point being there was no grounds for asking that question and we viewed it as highly inappropriate. Further, a tip was included in our bill, but it was insisted that we HAD to tip additionally. With a line behind us, and comments that had already been made, we did not want to make a scene, but ended up tipping about 38% for service that was “microaggressive” and condescending.
Allison Paige
Wanted to like this spot, but it’s the service for me. They are soooo rude here for no reason, extremely condescending about not knowing a lot about wine which I find very strange. Also, they automatically charge a 23% tip/fee although there isn’t much service happening considering you go up to a counter to order… also why would I want to tip people who are rude and make me uncomfortable. Also food is mid and so overpriced for what it is. Lastly, it’s a cute space but it is so dark in there it’s impossible to read the menus! Not to mention, the chairs are so uncomfortable and it makes it an unpleasant and not cozy experience. Biggest problem in my opinion is the entitled and rude staff.
Uncle June
Dear Annie offers a charming atmosphere but ultimately falls short in comfort and practicality. Most seats are small wooden stools crammed into tight corners around a large communal table. While the communal table is a creative concept, it’s not very functional. The table is too large to foster conversations with others across it, and it’s inconvenient for groups of more than two people.
When you arrive, a friendly server greets you and explains the bar, menu, self-service process, and seating arrangements. While this effort is appreciated, the amount of information can be overwhelming to take in all at once. Additionally, the menu itself is not user-friendly. The dim lighting and the neon text on neon paper, though visually distinctive, make the menu nearly impossible to read for most people and violate basic accessibility standards.
Pricing is another significant concern. While I support fair wages and employee appreciation, the cost here feels excessive given the self-service model. For instance, I paid nearly $100 for four glasses of wine, which is simply unrealistic.
A lack of transparency around the automatically added 23% gratuity is also problematic. Although the owner insists this information is displayed in multiple places, it is not obvious. My server never mentioned it, and the menu—already difficult to read due to its design—is a packet with an overwhelming amount of text on each page.
Unfortunately, the owner’s rude and defensive responses to negative reviews on here leave a bad taste as well. Engaging with customers in such a way feels unprofessional and uninviting.
Despite the ambiance, I don’t plan on returning due to the steep pricing and the dismissive tone toward customer feedback. For a better experience, I recommend nearby options like The Abbey, which offers more reasonable pricing, excellent service, and a unique atmosphere, or Cambridge Common, which provides great value, attentive service, and plenty of space. While they may lack the niche food and wine offerings of Dear Annie, both establishments make you feel genuinely respected and appreciated as a customer.
Parking: Street parking on Mass Ave. Some times are easier than others.
Atmosphere: 4
Service: 4
Recommended dishes: Cheesy Onion Roll
gali lior
Nice wine, limited food menu and very small portions, expensive, great atmosphere
Such a cute place, with an amazing selection of wines. I do recommend the cheese plate and cabbage dish! The staff was also very friendly:) Vegetarian friendly place!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Cheese Plate
Stacey Villani
Food and wine were great, but the 23% tip felt excessive for a partial self-serve place. Staff was helpful with wine picks. Overall, food quality was high but the price point seemed steep.
Atmosphere: 4
Food: 4
Service: 5
Doris Lin
Great wine bar in the neighborhood! We also got the wine club and was surprised by how delicious the wine was.
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Orange Wine
Helen
23% automatic gratuity added to your bill. Expensive and overrated.
Such a cute place and the staff are so knowledgeable. I don’t know much about wine but with a simple conversation about what I like they are always able to help me find something I love that’s also new and exciting.
The food is also delicious. Simple but well balanced and the salads are out of this world. The cod and whatever bean dish they are serving at the time are my other go-tos.
Cute and casual-looking place, but don't be fooled. It is exclusively for wealthy regulars and wine snobs. The servers are extremely rude if you don't fit in those categories. They'll give you disgusted looks for asking basic questions about their confusing menu and then stick you with an ALREADY INCLUDED 23% tip. They made me feel so uncomfortable, it was such a bad experience. Never going back.
This restaurant/wine bar was great when they first opened and has gone downhill ever since. I keep wanting to give it another try but after my last experience I’ve given up. Will not be going here ever again.
I was in here on a Sunday evening when a huge (and beautiful) display of foraged flowers fell over on the great table, and people were pros about it 👍🏽
Dear Annie is a cozy natural wine bar with a chill neighborhood feel. The wine selection is unique & carefully curated, the staff are knowledgeable, & the food delish.. grilled cheese, deviled eggs, & onion dip are all banging .. the 20% tip is, & has always been, standard in this industry so I don’t understand the hate there + 3% goes to the kitchen & that does not bother me in the slightest, as it’s very common on menus across the country these days. Please don’t go there expecting a red carpet to be rolled out in front of you (the entitlement in some of these reviews is real!) .. anyway drink natty!
Went to Dear Annie on a Thursday, 8:30pm with two friends. When ordering, we sent one group member to bar, and he was basically asked if he could afford what he ordered. We were all dressed well, groomed neatly — point being there was no grounds for asking that question and we viewed it as highly inappropriate. Further, a tip was included in our bill, but it was insisted that we HAD to tip additionally. With a line behind us, and comments that had already been made, we did not want to make a scene, but ended up tipping about 38% for service that was “microaggressive” and condescending.
Wanted to like this spot, but it’s the service for me. They are soooo rude here for no reason, extremely condescending about not knowing a lot about wine which I find very strange. Also, they automatically charge a 23% tip/fee although there isn’t much service happening considering you go up to a counter to order… also why would I want to tip people who are rude and make me uncomfortable. Also food is mid and so overpriced for what it is. Lastly, it’s a cute space but it is so dark in there it’s impossible to read the menus! Not to mention, the chairs are so uncomfortable and it makes it an unpleasant and not cozy experience. Biggest problem in my opinion is the entitled and rude staff.
Dear Annie offers a charming atmosphere but ultimately falls short in comfort and practicality. Most seats are small wooden stools crammed into tight corners around a large communal table. While the communal table is a creative concept, it’s not very functional. The table is too large to foster conversations with others across it, and it’s inconvenient for groups of more than two people.
When you arrive, a friendly server greets you and explains the bar, menu, self-service process, and seating arrangements. While this effort is appreciated, the amount of information can be overwhelming to take in all at once. Additionally, the menu itself is not user-friendly. The dim lighting and the neon text on neon paper, though visually distinctive, make the menu nearly impossible to read for most people and violate basic accessibility standards.
Pricing is another significant concern. While I support fair wages and employee appreciation, the cost here feels excessive given the self-service model. For instance, I paid nearly $100 for four glasses of wine, which is simply unrealistic.
A lack of transparency around the automatically added 23% gratuity is also problematic. Although the owner insists this information is displayed in multiple places, it is not obvious. My server never mentioned it, and the menu—already difficult to read due to its design—is a packet with an overwhelming amount of text on each page.
Unfortunately, the owner’s rude and defensive responses to negative reviews on here leave a bad taste as well. Engaging with customers in such a way feels unprofessional and uninviting.
Despite the ambiance, I don’t plan on returning due to the steep pricing and the dismissive tone toward customer feedback. For a better experience, I recommend nearby options like The Abbey, which offers more reasonable pricing, excellent service, and a unique atmosphere, or Cambridge Common, which provides great value, attentive service, and plenty of space. While they may lack the niche food and wine offerings of Dear Annie, both establishments make you feel genuinely respected and appreciated as a customer.
Parking: Street parking on Mass Ave. Some times are easier than others.
Atmosphere: 4
Service: 4
Recommended dishes: Cheesy Onion Roll
Nice wine, limited food menu and very small portions, expensive, great atmosphere
Atmosphere: 5
Food: 4
Service: 3
Perfect all around
Atmosphere: 5
Food: 5
Service: 5
Restaurantji Recommends
Great wine selection and vibe for great prices!
Atmosphere: 5
Food: 5
Service: 5
Such a cute place, with an amazing selection of wines. I do recommend the cheese plate and cabbage dish! The staff was also very friendly:)
Vegetarian friendly place!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Cheese Plate
Food and wine were great, but the 23% tip felt excessive for a partial self-serve place. Staff was helpful with wine picks. Overall, food quality was high but the price point seemed steep.
Atmosphere: 4
Food: 4
Service: 5
Great wine bar in the neighborhood! We also got the wine club and was surprised by how delicious the wine was.
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Orange Wine
23% automatic gratuity added to your bill. Expensive and overrated.
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