We recommend this as a 2nd or 3rd date where you can deepen your connection and see what your date gravitates to. You can learn a lot about a person by poking around little shops. HOw they interact with the owners, how quickly they can decide on which mini restaurant to choose at Bow (the secret is you don’t have to choose just one) Conveniently right off the green line – Union Sq in Somerville has so much to offer we could probably do 10 more date plans. But we will start here – because it’s a real crowd pleaser.
Neighborhood: Union Square, Somerville
Start time: 6:30 pm
Total cost: ~$25–45 per person
Overall vibe: playful, casual, conversational
The Date (Already Planned for You)
6:30 pm — Quick Dinner @ Bow Market
Start with a dinner at one of the many restaurants at Bow Market. There is seriously something there for every taste. If you arn’t in the mood for dinner you can grab cocktails at Nook or a local beer at Remnant.
This is the part of the date that gives you something shared to talk about without forcing conversation as you pop into vintage and craft shops
Typical cost: ~$12–18 per person
Location: 1 Bow Mkt Way, Somerville, MA
Order suggestion: Hop over to Carolicious for their Catira Arepas!
7:45 pm — Ice Cream at Gracie’s
Walk down the street to Gracie’s – Home of the Fluff Cone
I have a real sweet tooth, and it isn’t a date in Union square without Somerville’s best cone in your hand. Gracie’s hits just as good in July as it does in the middle of January.
See how willing your date is to share. Is it a trait or just a high value placed on ice cream? IT may take a few more dataes to find out.
Cost: ~$5–12 per person
Location: 22 Union Square, Somerville, MA 02143
8:ish pm —A Show!
If you’re both feeling it, wrap things up at The Jungle Community Music Club for a live show. They have something nearly everynight from local music showcases to comedy.
Sample upcoming option:
🎶 Bishop & in Motion/State Parque/ Crossing the line/ Caramia+The Breakroom
📅 Saturday, January 1, 2026
🎟️ Tickets typically ~$10–15
You’re standing or sitting close, reacting to music together, whispering little side comments. There’s a natural end when the show finishes, no awkward “so… what now?”
Location: 6 Sanborn Ct, Somerville, MA 02143 ·
Ticket link:
Events Calendar — The Junglehttps://www.thejunglemusicclub.com/events-calendar
Total Date Cost
- Dinner: $12–20
- Gracies: $5–12
- Final stop: $10–15
~$30–60 per person
Leave a Reply