Davis Square: Make It Cozy
Where: Davis Square, Somerville
When: January 17th, 6:00 – 10:00 PM
Total cost: ~$40–$50 per person
Vibe: Cozy, playful, low-pressure togetherness
The Date
6:00 PM – “Cozy and Community” BYO Boardgames
Wild Child Chocolates – 260 Elm St, Somerville, MA 02144
Event Info: Events/Workshops – Wild Child Chocolate
Drop in for drinking chocolate and BYO activity (crafts, board games, cozy winter vibes) at the new chocolate popup! Slip a deck of cards in your pocket
- Sipping chocolate: ~$6–8 per person
- Event cost: Free
7:30 PM – Quick Mexican Diner
Anna’s Taqueria – 236 Elm St, Somerville, MA 02144
Walk down the street to Anna’s for an unfussy burrito – you are fueling up before the show!
- Burrito or bowl: ~$10–12 per person
8:45 PM – Comedy Nightcap – Field Trip Live
The Rockwell Theater – 255 Elm St, Somerville, MA 02144
Tickets: Events for December 2025 – The Rockwell
Comedy is a phenomenal date move. It gives you shared reactions, something to laugh about, and an easy way to read each other’s sense of humor.
- Comedy ticket: ~$15–20 per person
Why This Date Works
This is a date built around togetherness without pressure.
You’re moving through the same neighborhood, sharing small experiences, and never forcing or rushing anything. There’s built-in conversation fuel (chocolate! comedy!), natural transitions, and multiple off-ramps if either of you needs them. Wild Child Chocolate gives you something to do with your hands and your attention -always helpful when you are first getting to know someone. Casual food first keeps everyone relaxed and on time. Comedy at The Rockwell creates shared laughter, which is one of the fastest ways people bond!
It’s got a lot of bang for your buck in just a 1 block radius.
More about these choices
- Wild Child Chocolate – Cozy, local eclectic, warm colors, surprisingly big
- I first went to Wildchild’s new popup a weekend after they opened. I saw a sign that said chocolate this way. I was sold sight unseen to go. I am a little-treat girlie Afterall. I walk into a warm large room. About two dozen people sat in tables hunched over little trays. The smell of chocolate and lush botanicals was everywhere. There was a workshop going on so the owner, Sarah, stopped to talk to me in-between guiding to the class. About two dozen people sat in tables with little trays looking quite pleased with whatever they were making. I didn’t pay too much attention since I had beelined back to the chocolate making section in the back where all th goodies were displayed. Single origin, interesting flavors. I remarked on how great it was to see something like this in one of the long vacant storefronts as i picked up a thai ginger lime chocolate bar for my fiancé.
- Anna’s Taqueria – Fast casual
- Yes, I know – it is a chain. a local one though! It is predictable – I know that every time I go there I can get the same Chimichurri burrito and it will be just as good. The nice thing about something so fast is that you can take as much or as little time as you want here. If you’d like to eat super speedy and then walk around the square a bit – you can do that! Or nurse that burrito over a cheesy queso dip until its time for the doors to open at the show.
- Comedy at The Rockwell – Unique, intimate, funny
- I love the Rockwell. They have all these small touring shows and local productions. If you can’t make it to this show, you really cant go wrong with any other one. To get there walk down the street from Anna’s. You open a heavy dark door and walk down a grand two-story flight of stairs that shares an entrance to one of my favorite cocktail bars – Saloon (more on them later) You are guided to the left where you will have your tickets taken and you can grab a drink while you enjoy the show. Its dark with raised seats overlooking a central stage. It’s so intimate – and calming and inviting – after a show you feel like you can just talk to everybody – although I can’t recall a time I have been there and haven’t run into somebody I know.
Want more date plans like this?
This series will keep highlighting local Boston area businesses, realistic budgets, and dates that actually help you connect – not just survive the night.
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