Skip the Small Talk Boston

Millennial Speed-Dating (Monogamous)

Sat, May 9 · 7:00 PM EDT

Scholars Boston Bistro & Cocktail lounge, 25 School Street, Boston, MA, US

###PLEASE NOTE: Even if you RSVP on Meetup, you will need to grab a ticket here https://www.skipthesmalltalk.com/store/millennial-speed-dating-monogamous-saturday-may-9-2026 in order to attend### This event is cross-posted so Meetup RSVPs won't accurately reflect the actual number of attendees; typically there are around 30-40 people in attendance.

Want to get off your dating apps and meet someone in real life, but where you don’t have to find out that every cute person at the party is unavailable? Do you think that IRL speed dating is generally awkward and weird? So do we. That’s why we’re putting a Skip the Small Talk twist on dating.

We'll be offering "big talk" conversation prompts 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.

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. Please note that there is an arrival cutoff, meaning that if you are not in line to check in before 7:10 pm, unfortunately, you will not be able to participate and we will not be able to offer refunds.

Skip the Small Talk is dedicated to providing an inclusive, welcoming environment for everyone. Check out our safety policy here: Skip the Small Talk Safety Policy

Who Is This Event for?

You would probably have a good time at this event if all of the following are true of you:

• You are aged 30-45 (plus or minus a year or two is cool, too, and if you’re not in this age range, feel free to check out our other events).
• You are monogamous (polyamorous events are also often available— feel free to check out our other Boston events!)
• You either feel a connection to the identity of “man” and you are interested in dating women, or you feel a connection to the identity of “woman” and you are interested in dating men. Gender nonconforming folks who feel connected to one of those genders in some way are absolutely welcome. (We also host other events to accommodate gender nonconforming folks who don’t feel a connection to the identity of “man” or “woman”).

If any of the above statements are NOT true of you, you might want to see if our other events are a better fit. We do our best to accommodate as many different demographics as possible given limited capacity for our speed-dating events, and we are always working to include more! Any suggestions for how we can be more inclusive? Please feel free to reach out to us at info@skipthesmalltalk.com.

This event is trans-inclusive. We do not tolerate transphobia at this or any of our events.

We can only accommodate a limited number of guests at this event, so please plan to grab a ticket as soon as you think you'd like to join us.

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.

If you want to be the first to hear about our events before we sell out, feel free to join our mailing list at Skip the Small Talk Mailing List Sign-Up

###PLEASE NOTE: Even if you RSVP on Meetup, you will need to grab a ticket here https://www.skipthesmalltalk.com/store/millennial-speed-dating-monogamous-saturday-may-9-2026 in order to attend### This event is cross-posted so Meetup RSVPs won't accurately reflect the actual number of attendees; typically there are around 30-40 people in attendance.

Skip the Small Talk Night at Aeronaut

Mon, May 18 · 6:30 PM EDT

Aeronaut Brewing Company, 14 Tyler St, Somerville, MA, US

###PLEASE NOTE: Even if you RSVP on Meetup, you will need to grab a ticket here https://www.skipthesmalltalk.com/store/skip-the-small-talk-night-at-aeronaut-monday-may-18-2026 in order to attend### This event is cross-posted so Meetup RSVPs won't accurately reflect the actual number of attendees; typically there are around 30-40 people in attendance.

What's It Like?

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- most people do!) and spend your Monday 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.

There will be food and beer for sale!

Check-in for this event will begin around 6:15 pm. Please do your best to arrive before 6:30 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: tinyurl.com/ststSafety

Please see our event page for more accessibility info.

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 Aeronaut? Check out their full event calendar here. If you want to be the first to hear about our events before we sell out, feel free to join our mailing list at Skip the Small Talk Mailing List Sign-Up

###PLEASE NOTE: Even if you RSVP on Meetup, you will need to grab a ticket here https://www.skipthesmalltalk.com/store/skip-the-small-talk-night-at-aeronaut-monday-may-18-2026 in order to attend### This event is cross-posted so Meetup RSVPs won't accurately reflect the actual number of attendees; typically there are around 30-40 people in attendance.

LGBTQIA+ Skip the Small Talk Night at Trident Books

Wed, May 20 · 7:00 PM EDT

Trident Booksellers & Cafe, 338 Newbury St, Boston, MA, US

###PLEASE NOTE: Even if you RSVP on Meetup, you will need to grab a ticket here https://www.skipthesmalltalk.com/store/lgbtqia-skip-the-small-talk-night-at-trident-books-wednesday-may-20-2026 in order to attend### This event is cross-posted so Meetup RSVPs won't accurately reflect the actual number of attendees; typically there are around 30-40 people in attendance.

What's It Like?

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- most people do!) 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.

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: tinyurl.com/ststSafety

Please see our event page for more accessibility info.

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 here. If you want to be the first to hear about our events before we sell out, feel free to join our mailing list at Skip the Small Talk Mailing List Sign-Up

Skip the Small Talk Night Online

Thu, May 28 · 7:00 PM EDT

·

Online

Online

###You'll need the event URL, so be sure to register in advance at https://www.skipthesmalltalk.com/store/skip-the-small-talk-night-online-thursday-may-28-2026 so we can send it to you. We'll send you an e-mail with the Zoom link a few minutes after you purchase a ticket (and we'll also send it again the day of the event)-- please check both your “spam” AND “junk” folders if you don't see it!###

You may expect this event to run from 7:00-8:15pm ET/ 6:00 - 7:15 pm CT/ 5:00 - 6:15 pm MT/ 4:00 - 5:15 pm PT. Please be aware of time zone differences.

These Zoom events are designed based in psychology research to give you all the warm fuzzy feelings of human closeness, without that feeling of Zoom-fatigue afterward.

We use question prompts and a structure designed based in psychology research to help you get vulnerable with strangers in a way that actually feels safe, and that brings out the best in people.

All our events are trauma-informed and facilitated by folks with therapeutic training. According to our surveys, a lot of our guests report feeling nervous about coming, but 100% of the people who say they were nervous also end up saying they were glad they came. There might be some selection bias going on, but we still think it's promising :)

We even had an academic paper come out about our online events showing that they improve mood and reduce loneliness! Check that out here.

What's it like?

The whole thing is on Zoom.

We'll put you into pairs in breakout rooms, and you'll switch partners so you're not just talking to the same person the whole night.

We'll give you question prompts to spark conversations to make sure you're getting the most out of your conversations.

Some examples of our research-backed prompts are, "What's something you're proud of that you don't usually get to share with people?" And, "What's something I would need to know about you in order to be friends with you?"

But if you hate our prompts, you'll always be invited to make up your own or talk about whatever feels right.

What do people say about it?

Here's some stuff people have told us (unprompted!) about the online Skip the Small Talks:

"I was surprised at how good this was! I'll definitely be coming back!"

"This has turned into my weekly self-care-- going to this event every week is something kind I do for myself to stay sane."

"I'm an introvert, and to be honest, I even think of myself as someone who generally hates other people, but I actually feel energized after Skip the Small Talk online. For some reason, I feel Zoom fatigue in pretty much every other online interaction, but I'm usually, like, giddy after these."

Ready to Skip the Small Talk with us?

You can grab a ticket here.

Please do your best to arrive a couple minutes before 7pm ET/ 6pm CT/ 5pm MT/ 4pm PT if you haven't been to one of these before so you don't miss the intro, but feel free to come late if you need to-- you'll still be able to participate just fine!

If you've come to an online Skip the Small Talk before and would rather skip the intro, feel free to come at 7:10 pm ET/ 6:10 CT/ 5:10 MT/ 4:10 PT.

Skip the Small Talk is dedicated to providing an inclusive, welcoming environment for everyone. Check out our safety policy here.

Need accessibility accommodations?

Please see ticket page for more details.

Want to keep up with our events?

If you want to be the first to get access to tickets, and also get free exclusive content about how to improve your relationships, communicate more effectively, and more deeply, join our mailing list (don't worry, we hate mailing lists, too-- we only e-mail when we have something useful to tell you about, like new events).

If you are interested in buying Skip the Small Talk question prompt cards to use in your everyday life, you can check those out here

###FYI that Meetup might say that "you're going" if you RSVP as "going," but you'll need to sign up at [https://www.skipthesmalltalk.com/store/skip-the-small-talk-night-online-thursday-may-28-2026]

This event is being cross-posted, so the number of RSVPs shown won't accurately reflect the number actually attending.

Hope to have you there!