Dear Annie — Restaurant in Cambridge

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...

I have a lot to say about this spot.

I really like the vibe, it's super aesthetic and food and wine are great. If that is all you wanted to know stop reading here and go. Vibe was pretty good, and made for a fun date night overall. Definitely makes sense for that area.

But..... because I do NOT live in that area, and am an average human here is my 2 cents.

I went here on a Monday night, and was a little confused by the communal seating vibe. It felt more like one communal table and then a bunch of private areas to sit that weren't communal. If it is communal seating I think they should go all in on that vibe.

We asked to move from the window sill to the communal table because they wasn't a ton of space to eat, and wasn't super cozy. They were accommodating and allowed us to move which was nice.

I know all the reviews say this, but that 23% added gratuity really took me by surprise. I could get behind that if it was full waitstaff service, but you walk up to the front to order, then it was pretty impossible to get a severs attention when they walked around. I understand they use very high quality local wines and ingredients, but I'd rather that be factored into the menu prices than added as a gratuity when there was very minimal wait service.

I told the woman what kind of wine I liked without looking at the menu, and she said they didn't have that there. She let me try one and without telling me the price poured two glasses of it and it ended up being more than I would have liked to pay for that particular wine. Turned out after seeing the menu they actually did have the wine I was looking for so that kind of...

Pretty awful experience, because the food and wine are not that great but the bad 'service' (there really isn't any to speak of) puts the experience over the edge from 'mediocre' to 'I'll never return'.

Nothing earth-shattering to say here that you haven't read from others, but just to add to the chorus: the vibe is oddly attitude-y (from the staff!)--even when they're not busy (we were first in line when they opened at 5pm), and you get the sense that they don't want to deal with you, ask questions or be helpful in any way. That would be slightly less annoying if the food and wine choices were stellar or amazing in any way, but they're not. Staff skews young and not knowledgeable about the food or wine on deck. We tried two different wines and 3-5 appetizers....all pretty basic, I'll term it as 'elevated fast food'.

For those to whom comfort is important: the chairs are hella uncomfortable; at 5pm, the sun (depending upon time of year) is blasting in your face; the staff won't bring anything so you're jumping up and down from your 1st grade-sized chair to get everything you need that didn't come with the food, and they don't have the tables organized in a way that maximizes customer comfort.

After our apps and wine, we were so hungry, we went down the street to Giulia's for a real dinner.

Overall, to help you avoid our mistakes, here's my best advice: skip Dear Annie and just go to Giulia's, sit at the bar, and have some truly good wine and freshly-made food from people who know how to run...