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Skip the Small Talk Night at Castle Island Brewing (South Boston) at Castle Island Brewing - South Boston

Skip the Small Talk Night at Castle Island Brewing (South Boston)

A host pairs attendees and rotates partners while question cards guide deeper conversation. Open to ages 21+; attendees may come alone or bring a friend.

AI summary · From the event listing

November 11, 2026 · 7 PM – 9 PM

Castle Island Brewing - South Boston · Free ·

Keep your plans in one place. Free account.

Website on Luma

Hosted rotating pairs and question cards give attendees a structured way to have deeper conversations; it is 21+ and explicitly not dating.

AI · From the event listing

Organizer’s description

This Skip the Small Talk event is affiliated with Boston Human Week. A paid ticket purchased directly through skipthesmalltalk.com is required to attend. A free Luma RSVP, even if approved, is not admission and does not reserve a ticket. Buy your ticket: https://www.skipthesmalltalk.com/store/skip-the-small-talk-night-at-castle-island-brewing-south-boston-wednesday-november-11-2026 This is an in-person event at Castle Island Brewing (South Boston), 10 Old Colony Ave, South Boston, MA 02127, on Wednesday, November 11, 2026, from 7–9 pm ET. Check-in begins at 6:45 pm. Open to everyone 21+; please bring a government-issued ID. You’ll pair up with the other nice people who showed up, and you’ll switch off partners every so often (kinda like speed-dating, but without the speed and without the dating). We’ll have a fabulous host leading the whole shebang, and we’ll give you question cards to guide conversation just a few notches deeper than you’d usually go so you don’t accidentally talk about what you do for work six times in a row. If you don’t vibe with a question for any reason, you can always pick another one! Feel free to come alone (most people do, and we promise we won’t make it weird for you) or bring a friend!

Hosted by Ashley Kirsner

Social · 6 PM · South Boston