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
Atmosphere: 5
Food: 4
Service: 3
Danielle Ishak
Perfect all around
Atmosphere: 5
Food: 5
Service: 5
Andrew Ciacci
Great wine selection and vibe for great prices!
Atmosphere: 5
Food: 5
Service: 5
Heetika Gada
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.
Matt Tillinghast
23% tip was added to my bill without the restaurant telling me first
Atmosphere: 3
Food: 2
Service: 1
Recommended dishes: Chocolate Brownie
Gabriella Bauer
Super duper cute place with outdoor seating and friendly service.However, I paid a whopping $38 for TWO SMALL glasses of red wine. Weak pour. Nothing else included. For that price, at least throw in some olives or bread.Absolutely insane. Afterwards, I went next door to the wine shop to get the same wine for $9. Unless you have more money than brains, I do not recommend this wine bar.
Love the vibe here! It’s a perfect place to hang in the mid-late afternoon and have a glass of wine before dinner. The staff is incredibly helpful to help you choose the right wine for you (and always give you a generous pour). I adore all of their flower arrangements on the communal table - unique, artsy, and just gorgeous. I also support the 23% service fee upfront, as 1 - it’s worth it and 2 - I prefer not to deal with bills or payments later on (which would be disruptive to the flow of the hangout).
Atmosphere: 5
Food: 5
Service: 5
Julie Mahdavi
Loved it! went for a glass of wine - a little pricy but nice ambiance
Atmosphere: 5
Food: 5
Service: 5
Anna K.
Absolutely fantastic food and wine, and beautiful, modern and whimsical place to hang out. Very recommended!
Atmosphere: 5
Food: 5
Service: 5
Natalia Banasik-Jemielniak
Very nice relaxed place to have a glass of wine
Atmosphere: 5
Food: 5
Service: 5
Mia-Fei Lapointe
Absolutely love! A natural wine, aesthetic haven. The menu is fresh and tasty, wines are crisp and delish. A hip, vibey spot. I recommend
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
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.
23% tip was added to my bill without the restaurant telling me first
Atmosphere: 3
Food: 2
Service: 1
Recommended dishes: Chocolate Brownie
Super duper cute place with outdoor seating and friendly service.However, I paid a whopping $38 for TWO SMALL glasses of red wine. Weak pour. Nothing else included. For that price, at least throw in some olives or bread.Absolutely insane. Afterwards, I went next door to the wine shop to get the same wine for $9. Unless you have more money than brains, I do not recommend this wine bar.
Atmosphere: 3
Service: 3
Restaurantji Recommends
Love the vibe here! It’s a perfect place to hang in the mid-late afternoon and have a glass of wine before dinner. The staff is incredibly helpful to help you choose the right wine for you (and always give you a generous pour). I adore all of their flower arrangements on the communal table - unique, artsy, and just gorgeous. I also support the 23% service fee upfront, as 1 - it’s worth it and 2 - I prefer not to deal with bills or payments later on (which would be disruptive to the flow of the hangout).
Atmosphere: 5
Food: 5
Service: 5
Loved it! went for a glass of wine - a little pricy but nice ambiance
Atmosphere: 5
Food: 5
Service: 5
Absolutely fantastic food and wine, and beautiful, modern and whimsical place to hang out. Very recommended!
Atmosphere: 5
Food: 5
Service: 5
Very nice relaxed place to have a glass of wine
Atmosphere: 5
Food: 5
Service: 5
Absolutely love! A natural wine, aesthetic haven. The menu is fresh and tasty, wines are crisp and delish. A hip, vibey spot. I recommend
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Cheese Plate, Arctic Char Tartare, Chardonnay
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