01/23/2026
Boston Dates, Planned for You: Union Square
As a matchmaker and singles event planner, I spend a lot of time thinking about what actually makes dates work.
This Union Square plan is especially good as a second + date. Variety is built in at every turn you’re walking, tasting, browsing, reacting which keeps things light, a little dopamine-filled, and easy to stay present. That's where the magic happens!
🛍 Bow Market (food + artsy & vintage shops)
🍦 ice cream Second (A must, even in January)
🎶 live music or open mic at The Jungle if you’re feeling it
Read the blog for why this date works and all the details.
Comment UNION for the link.
Blog Features: market somerville
What neighborhood should I feature next?