Hannah Bernstein

Suffolk County

Boston Metropolitan Area

Boston

Massachusetts

North End

Beacon Hill

Back Bay

Charlestown

South End

Fenway

Middlesex County

Cambridge

Benjamin Pierce

Somerville

Jamaica Plain

Norfolk County

Brookline

Trident Booksellers & Cafe

Bring your friends (or come by yourself) and spend your Wednesday night at an event where you know everyone else is there for the same reason.
What’s It Like? Hear from real attendees in the videos at the bottom of the page!
Do you wish you could have more of the kinds of conversations you have late at night where for some reason, you feel safe talking about the things you actually care about?
Bring your friends (or come by yourself) and spend your Wednesday night at an event where you know everyone else is there for the same reason.
We'll be offering "big talk" conversational prompts on them to get you started, and we'll have lots of structure to make sure that you actually talk to people and that it's not awkward. Not feeling like answering a particular question? No worries, we'll have plenty to choose from, like, "When are you the happiest?" and, "If you were going to become close friends with me, what would I need to know about you?" We'll give you ground rules to make sure you feel comfortable and safe sharing as much of yourself as possible while still feeling in complete control of how much you divulge.
There will be food and drinks for sale!
Check-in for this event will begin around 6:45 pm. Please do your best to arrive before 7:00 pm so we can begin as close to on time as possible.
Skip the Small Talk is dedicated to providing an inclusive, welcoming environment for everyone. Check out our safety policy here: <a href="https://tinyurl.com/ststSafety" rel="nofollow noopener" target="_blank">tinyurl.com/ststSafety</a>
 Ready to Skip the Small Talk With Us? Grab a ticket since entry is on a first come first serve basis and we tend to sell out in advance for these-- once we are out of tickets, we will NOT be able to accommodate folks at the door.
Want to check out what else is going on at Trident Books? Check out their full event calendar <a href="https://www.tridentbookscafe.com/event" rel="nofollow noopener" target="_blank">here</a>. If you want to be the first to hear about our events before we sell out, feel free to join our mailing list at <a href="https://sendfox.com/skipthesmalltalk" rel="nofollow noopener" target="_blank">Skip the Small Talk Mailing List Sign-Up</a>.
See our Skip the Small Talk question prompt card deck (and buy your own if you want) <a href="https://www.amazon.com/Skip-Small-Talk-Card-Deck/dp/1507221975/" rel="nofollow noopener" target="_blank">here</a>.
If you want to get more of a vibe of what our events are like, have a look at the videos below and check out our <a href="https://www.skipthesmalltalk.com/faq" rel="nofollow noopener" target="_blank">FAQ</a> (which also covers stuff like our refund policy, arriving late, age range, and hiring us for corporate/ college/ private events).

Local Event: Skip the Small Talk Night at Trident Books

Skip the Small Talk Night at Trident Books

Bring your friends (or come by yourself) and spend your Wednesday night at an event where you know everyone else is there for...

<a href="https://www.schooloffashiondesign.org/" target="_blank" rel="nofollow noopener">School of Fashion Design, Boston</a> - Summer 2026 - June 8th to August 14thCheck out our beginner friendly courses with no prerequisites!<ul><li><a href="https://schooloffashiondesign.asapconnected.com/#CourseID=152102" target="_blank" rel="nofollow noopener">Construction Clothing 1</a>instructs students on how to cut, hand sew, and use an industrial machine. Students are also trained in lining, pressing, detailing, and finishing! Tuesdays &amp; Thursdays, 9:15 AM - 11:30 AM or 5:30 PM - 7:45 PM</li><li><a href="https://schooloffashiondesign.asapconnected.com/#CourseID=152098" target="_blank" rel="nofollow noopener">Pattern Making 1</a> introduces students to the principles, techniques and practice of draft flat patterns for women's garments! Students learn how to create block drafts, slopers, and patterns. Tuesdays and Thursdays, 12:00 PM - 2:15 PM&nbsp;or&nbsp;7:45 PM – 10:00&nbsp;PM</li><li><a href="https://schooloffashiondesign.asapconnected.com/#CourseID=152096" target="_blank" rel="nofollow noopener">Fashion Sketching 1</a> teaches students the necessary principles and techniques of fashion sketching to create their own fashion plates. Tuesdays and Thursdays, 2:30 PM - 4:45 PM or&nbsp;06:00 PM – 08:15 PM</li><li><a href="https://schooloffashiondesign.asapconnected.com/#CourseID=152110" target="_blank" rel="nofollow noopener">History of Costume</a> dives into costumes from ancient to modern times, with a focus on contemporary design and theatrical costuming. Students will study the fabrics, colors, styles, cultural and psychological impacts of these garments throughout history. Mondays and Wednesdays, 9:15 AM - 11:30 AM</li><li><a href="https://schooloffashiondesign.asapconnected.com/#CourseID=152109" target="_blank" rel="nofollow noopener">Fundamentals of Textile</a> offers a necessary comprehensive understanding of the fibers and fabrics with which you will work with as a fashion designer. Mondays &amp; Wednesdays, 12:00 PM - 2:15 PM</li><li><a href="https://schooloffashiondesign.asapconnected.com/#CourseGroupID=65518" target="_blank" rel="nofollow noopener">Check our catalogue</a>, register today, or email admissions@sfdboston.org to get started!</li></ul>

Local Event: School of Fashion Design - Now Enrolling for Summer 2026

School of Fashion Design - Now Enrolling for...

School of Fashion Design, Boston - Summer 2026 - June 8th to August 14thCheck out our beginner friendly courses with no...

School of Fashion Design - Now Enrolling for Summer 2026

Online

Join this free <a href="https://www.brickmarketing.com/webinars" target="_blank" rel="nofollow noopener">AI marketing webinar by Brick Marketing on 6/10/26</a> to learn how modern SEO, AI search, and content work together to drive trust and visibility. Discover the signals that attract business and generate better leads through these essential digital marketing strategies. For more information, please visit: <a href="https://www.brickmarketing.com/webinars" target="_blank" rel="nofollow noopener">brickmarketing.com/webinars</a>

Local Event: AI Marketing Webinar: Generate Better Leads With SEO, AI Search (GEO) & Content Marketing

AI Marketing Webinar: Generate Better Leads...

Join this free AI marketing webinar by Brick Marketing on 6/10/26 to learn how modern SEO, AI search, and content work together...

AI Marketing Webinar: Generate Better Leads With SEO, AI Search (GEO) & Content Marketing

Pier 4, Charlestown Navy Yard 

Courageous Sailing's signature summer event is back again on Pier 4 in the Charlestown Navy Yard! Join us under the tent for an unforgettable evening of live music from Soul of Boston, light bites and drinks, dancing, silent and live auctions, fantastic company, and dazzling views of the Boston skyline . . . all in support of Courageous Sailing's free sailing and learning programs for metro Boston kids!
Visit <a target="_blank" href="https://courageoussailing.org/fundraising-events/makeamark/" rel="nofollow noopener">https://courageoussailing.org/fundraising-events/makeamark/</a> for tickets, sponsorship opportunities, and more information.

Local Event: Make-A-Mark 

Make-A-Mark 

Courageous Sailing's signature summer event is back again on Pier 4 in the Charlestown Navy Yard! Join us under the tent for an...

Regent Theatre

The Look, the Music and the Moves are what everyone remembers from the movie that became a cult classic. Great Songs, Awesome Dance moves and High Energy is what makes “HATS AND SHADES” the most exciting tribute in the USA. Gene DiNapoli as Jake Blues and Lamar Peters as Elwood Blues recreate the live concert that brought their brand of soul and rhythm and blues to the country after their skit got rave reviews on “Saturday Night Live” Get tickets at <a href="https://www.regenttheatre.com/?fbclid=IwZXh0bgNhZW0CMTAAYnJpZBExS2lqNTdWMkxaYjc0S1dhcHNydGMGYXBwX2lkEDIyMjAzOTE3ODgyMDA4OTIAAR7GzCNYCo0M9YqpjV4kXb3COBoLVeoTrknaEo3LqsogwL2k1LgG0EMTlF87YQ_aem_w_u9PWy2bf3bOF3cWgjOEA" target="_blank" rel="nofollow noopener">www.regenttheatre.com</a> or call 781 646 4849

Local Event: "Hats and Shades" Blues Brothers  Tribute Show in Arlington Mass.

Arlington

"Hats and Shades" Blues Brothers  Tribute Show...

The Look, the Music and the Moves are what everyone remembers from the movie that became a cult classic. Great Songs, Awesome...

"Hats and Shades" Blues Brothers  Tribute Show in Arlington Mass.

Greater Boston Real Estate Market Update: Prices Up, Sales DownAfter a slow start to 2026, single-family and condominium sales rose modestly in April, but were down through the first four months of the year in Greater Boston, according to data compiled by The Warren Group. Greater Boston <a href="https://info.buyersbrokersonly.com/home-listings?patch" target="_blank" rel="noopener nofollow">single-family sales</a> rose by 48 units, a 3 percent increase in April, but were down 2 percent during the first four months of the year compared to the same timeframe in 2025. The Warren Group, a publisher of real estate data, defines Greater Boston as the 139 cities and towns within Interstate 495. The median house price rose 2 percent to $815,000 in April from $799,000 in April 2025. The median price also increased by 2 percent during the January-through-April period to $779,750 from $765,000 during the same period last year.&ndash;&gt;&nbsp;<a href="https://info.buyersbrokersonly.com/guide-to-the-home-buying-process-massachusetts" target="_blank" rel="noopener nofollow">Download the Massachusetts Homebuyer Guide</a><a href="https://info.buyersbrokersonly.com/12-condo-questions" target="_blank" rel="noopener nofollow">Condominium</a> sales rose by 32 units, or almost 3 percent, year over year in April. Sales slipped 2 percent through April compared to the first four months of 2025. Condominium prices in Greater Boston fell in April and through the end of April. The median condo price declined by more than 1 percent to $620,000 in April, down from $629,000 in April 2025. Through the first four months of 2026, the median condo price dropped 5 percent to $595,000 from $625,000 during the same four-month period last year. <a href="https://info.buyersbrokersonly.com/blog/massachusetts-home-prices-rose-in-april-as-sales-slowed" target="_blank" rel="noopener nofollow">Statewide</a>, there were only two months of single-family inventory in April, according to the Massachusetts Association of Realtors. &nbsp;The condo market had about three months of supply. About five months of inventory is considered a balanced market between homebuyers and sellers.Learn About Down Payment Assistance: <a href="https://info.buyersbrokersonly.com/blog/ma-down-payment-assistance-who-qualifies-for-the-0-interest-program" rel="noopener nofollow" target="_blank">info.buyersbrokersonly.com/blog/ma-down-payment-assistance-who-qualifies-for-the-0-interest-program</a>Homebuyers Should Understand Buyer Agency Agreements: <a href="https://info.buyersbrokersonly.com/blog/understanding-buyer-agency-agreements-a-guide-for-homebuyers" rel="noopener nofollow" target="_blank">info.buyersbrokersonly.com/blog/understanding-buyer-agency-agreements-a-guide-for-homebuyers</a>

Greater Boston Real Estate: April 2026 Update

Greater Boston Real Estate Market Update: Prices Up, Sales DownAfter a slow start to 2026, single-family and condominium sales rose modestly in...

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Skip the Small Talk Night at Trident Books

School of Fashion Design - Now Enrolling for Summer 2026

AI Marketing Webinar: Generate Better Leads With SEO, AI Search (GEO) & Content Marketing

Make-A-Mark

"Hats and Shades" Blues Brothers Tribute Show in Arlington Mass.

Greater Boston Real Estate: April 2026 Update