Chicago 20's & 30's Group

###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-kibbitznest-wednesday-january-14-2026 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.

Learn more about kibbitznest and their mission on their website 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-kibbitznest-wednesday-january-14-2026 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.

If you're single in Chicago and want to meet other singles in a laid back, welcoming environment where it's easy getting to know new single friends and making a connection, MEETUP with us on Thursday Nights for a 5-week, 80-100 player Singles Skeeball League! We'll place you on a coed team of 9 guys and 9 girls around your age, and it's THE BEST thing ever!! And you definitely don't need skeeball skills to join, it's just for fun :)

Seeing the same people for 5 weeks in a row makes it really easy to build lasting relationships other over the season!

FULL DETAILS & SIGN UP HERE: https://s3leagues.com/winter-leagues/thursday-sluggers-singles-skeeball-season-1

REGISTER BY YOURSELF OR WITH FRIENDS. Team are made by age group for anyone aged 21-48. Prefer younger or older teammates, just let us know! Every night you play a skeeball match against a different team, have a few drinks, get FREE batting cages and enjoy dueling pianos afterward to keep hanging out. And it's totally okay to miss a night here and there if you need to.

Maybe you meet someone you vibe with to go on a date, maybe you make some new single friends. Either way you will have an amazing season and make lots of new connections! There's a reason why this league has filled up every time for the last 42 seasons.

THE BEST PART: IT'S ONLY $65 FOR ALL 5-WEEKS! That's just $13 per night for the best way to meet other singles in Chicago :)

ADDITIONAL LEAGUE DETAILS:

*Don't pay attention to the RSVP #. I promote this league in many places and it always sells out!

First Games: Thursday, November 6th - 5 week season ending Dec 11th (no games Nov 27th for Thanksgiving)

Games Start: 6:50, 7:40 or 8:30 pm (your game time changes each week)

Length: 5 Weeks. The final night is a playoffs tournament!

Location: Sluggers (3540 N Clark St) in Wrigleyville

League Fees: Only $65 total per player for all 5 weeks!

FULL DETAILS & SIGN UP HERE: https://s3leagues.com/winter-leagues/thursday-sluggers-singles-skeeball-season-1

Send me a direct message if you have any questions at all. I hope to see you there ;)

Cheers, Ben

We all know Family Feud! The best game show ever right!? I came up with an amazing way to play bar trivia like the Family Feud game show that anyone can play and be good at! You don't have to know lots of random facts to enjoy or win this trivia. I've done over 25 seasons of this too!

Check out the video I made showing how much fun it is: https://youtu.be/GcAlp9lR_QE

This league is a super fun way to meet new people, have some mid-week drinks and get your think on! They give us really amazing exclusive specials too! It ALWAYS fills up with 140ish people playing, so the RSVP # will not reflect the actual size.

You can register online by yourself or with friends for only $35! We'll then put you on a coed team of 6 thinkers around your age for the season and email you a bunch of info to know for the season. Or sign up your own team of up to 6 people for just $150!

CHECK OUT THE FULL DETAILS AND REGISTER HERE: https://s3leagues.com/winter-leagues/thursday-family-feud-trivia-season-1

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LEAGUE DETAILS:
First Games: Thursday, February 5th
Final Games: Thursday, March 5th
Start/End Time: 7:00 - 9:00 pm
Location: The River Kitchen & Bar (2909 N Sheffield Ave)

HOW WE PLAY:
Each night there are 2 rounds of 5 questions. The trivia works in reverse of how traditional Family Feud scoring goes. Teams are given the survey question that people were asked and then you have to turn in only one answer. BUT you get the MOST points for guessing the lowest answer on the list (the one that only a couple people said) and LESS points for guessing the popular answers! So it's a battle between making sure your answer is on the on the list of answers given but as far on the bottom of that list as possible. It's THE BEST kind of trivia ever.

We give out really awesome prizes too!! NIGHTLY PRIZES FOR THE TOP 8 TEAMS!!! PLUS INCREDIBLE OVERALL LEAGUE PRIZES!!!

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League Fees: Only $35 per person for the entire 5-week season or $150 to register a full team of up to 6 people.

CHECK OUT THE FULL DETAILS AND REGISTER HERE: https://s3leagues.com/winter-leagues/thursday-family-feud-trivia-season-1

Please message me if you have any questions and I hope to see you there!

Cheers,
Ben

The Laugh Factory in Lakeview (Broadway & Belmont) is open for comedy and we all could use some laughs! We always get A LOT of people to attend these shows. Often times over 100 Meetup members!

If you attend by yourself or with friends and want to be seated in the Meetup group section, simply request this when you check in at the ticket booth! Then just say hi to those around you :)

Every First Friday of the month we get $5 TICKETS to their shows at 7:00, 9:15 & 11:30 pm. They're ALWAYS hilarious!

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Get your $5 tickets ASAP before the quantity they give us get sells out. And with our "laugh or get a refund" policy (that has never in 4 years been requested), I know you'll enjoy your MUCH NEEDED night out! This event is posted in lots of different Meetup groups, so the RSVP # won't show how many are actually attending.

READ THE DESCRIPTION OF EACH SHOW AND GET YOUR $5 TIX HERE: https://tinyurl.com/firstfridayslaughfactory

*You can purchase tickets for several people and multiple shows this night through the link. No physical tickets will be issued. Your name will be on a list at the door and all tickets will be under the purchaser's name. Groups of up to 6 people can be sat together if arriving together.

Please Note: These shows are for ages 18+ w/ ID. If you show up after start time you will not be able to enter. There is a 2 drink minimum per person per show (non-alcoholic or alcoholic). Drinks are reasonably priced, and a comedy show is funnier with a few drinks, so this shouldn't be an issue with how cheap our tickets are :) Also, an 18% service fee (aka gratuity) will be applied to all drink tabs at payment to be given directly to service staff.

No refunds or exchanges but tickets can be transferred.

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Is there parking? Street parking and some garages are available throughout the area. However, public transit, ridesharing apps, and taxi services are highly encouraged.

What is the dress code? There is no dress code. Be comfortable!

READ THE DESCRIPTION OF EACH SHOW AND GET YOUR $5 TIX HERE: https://tinyurl.com/firstfridayslaughfactory

Enjoy the laughter!

-Ben