Skip the Small Talk Night @ Aeronaut Brewing, Somerville — Escape the "what do you do for work" cycle and dive straight into meaningful, structured "big talk" prompts designed to spark the kind of deep, late-night energy that actually builds real friendships | $24, 6:30PM-8:30PM

Tavern Talk @ Aeronaut Brewing, Somerville — A brewery-hosted history night at Aeronaut Brewing with the Somerville Museum digging into Henry Knox’s winter artillery haul and its role in breaking the siege of Boston | $12, 7PM-10PM

Craft Night @ Cafe Zing!, Cambridge — A drop-in craft night where you can bring your own project or use shared supplies to make valentines, collage, sew, or draw while grabbing drinks and free samples from Cambridge Naturals | FREE, 5PM–7PM

V-Day DIY Class: Chocolate Decoration & Flavor Design @ Mamaleh’s Delicatessen, Cambridge — A hands-on Valentine’s chocolate workshop where you’ll design, mold, and decorate your own custom chocolate heart with guidance from Wild Child Chocolate inside Kendall Square | $36, 6:30PM–8PM

Galentine’s Charm Bracelet Class @ Jamie’s Ice Cream Co., Somerville — A Galentine’s bracelet-making class where you’ll design a 14k gold-filled bracelet using five selectable charms with all materials and tools provided | $80, 7PM–8:30PM

Foundry Festival 2026 @ The Foundry, Cambridge — A free, weeklong community festival filling The Foundry with hands-on art workshops, STEM activities, live performances, science demos and family-friendly programs you can drop into any day | FREE, Feb 14–21

Rosé & Roses 2026 @ Kendall Center Pioneer Room, Cambridge — A low-effort Valentine’s plan built around complimentary rosé, floral arranging, and a first-come bloom bar designed for stopping by with friends or coworkers | FREE, 4PM–6PM

Books & Brews @ Aeronaut Brewery, Somerville — This recurring book club pairs a shared read with in-person discussion at a brewery, focusing each meeting on one book and inviting thoughtful, lively conversation around the month’s selection — this month’s book is The Fox Wife by Yangsze Choo | FREE, 6:15PM–7:30PM

Big Valentine’s Singles Bash @ Bow Market, Somerville — A one-night singles takeover featuring flirty fast-paced games, curated conversation rounds, themed cocktails, and a no-pressure calling card system designed for ages 26–38 | $34, 7PM–9PM

On Tap at Aeronaut: The Berklee Music Series @ Aeronaut Brewing Company, Somerville — Catch the next big thing in music every Wednesday night as up-and-coming student artists from the Berklee College of Music take the stage for a live performance in the taproom | FREE, 7PM-9PM

Line Dancing Wednesdays @ McCarthy’s Upstairs, Cambridge — Line dancing without a partner or prep where you can jump into taught dances, miss a round, and rejoin as lessons repeat | FREE, Wednesdays 8:30PM–11:30PM

Crafternoon @ MIT Welcome Center, Cambridge — Leave with hand-printed valentines after a free afternoon of carving stamps, rolling ink, and learning simple block-printing techniques in a relaxed creative setup | FREE, 4PM–6PM

Chocolate & Cocktails: A Galentine’s Experience @ The Row Hotel at Assembly Row, Somerville — A Galentine’s night built around hands-on chocolate making and guided cocktail crafting where dessert and drinks collide in a social, flavor-first experience designed for celebrating together | $80, 6PM–7:30PM

Drink & Doodle & Dates @ Aeronaut Brewing, Somerville — Part art hang, part social mixer, this Valentine’s week event blends drinking, drawing, and low-stakes mingling with built-in activities and a subtle wear-black cue to spark conversation | FREE, 7PM–9PM

Millennials Speed-Dating @ McCarthy’s Upstairs, Cambridge — A structured speed-dating night for monogamous millennials ages 30–45 featuring timed one-on-one conversations, guided rotations, check-in at 6:45PM, and food and drinks available for purchase | $55, 7PM–9PM