If you had asked me back in 2009 what business I was getting into, I probably would have said sports leagues.
Today, after watching more than 130,000 people play with S3 Leagues, I’d answer that question very differently.
I don’t think we’re really in the sports business.
I think we’re in the people business.
That might sound like a strange thing to hear from someone who organizes kickball, softball, volleyball, bowling, dodgeball, skeeball, and other recreational leagues across Chicago.
But stick with me for a minute.
Nobody has ever emailed me years later because they still can’t stop thinking about a game they won on a random Wednesday night.
That’s not what people remember.
They remember the teammate who made everyone laugh before every game.
They remember staying at the sponsor bar until closing because nobody wanted the night to end.
They remember finally taking that group vacation they’d been talking about for three years.
They remember the proposal on the field that surprised everyone.
They remember teammates who became roommates.
They remember weddings.
We’ve even had former players bring their kids back years later to watch the games because that’s where Mom and Dad met.
One longtime player turned years of old S3 shirts into a quilt because every shirt reminded them of another season, another team, and another chapter of life.
Those are the memories that last.
Not because people were playing sports.
Because they were spending time with people they genuinely enjoyed being around.
Over the years I’ve realized something that applies whether you’re joining a sports league, starting a trivia team, volunteering, taking a cooking class, or simply trying to reconnect with old friends.
The activity almost doesn’t matter.
What matters is creating regular opportunities to be around people.
That’s what this guide is about.
Not becoming more outgoing.
Not collecting hundreds of friends.
Not filling every night on your calendar.
It’s about building a life where you’re excited when Wednesday rolls around because you already know you’ll be spending it with people you enjoy.
Whether you’re new to Chicago…
You’ve lived here your whole life…
You’re hoping to make friends in Chicago as an adult…
Or you’re simply tired of texting, “We should get together sometime,” without anyone ever actually picking a date…
This guide is for you.
Nobody Told Us Adult Friendships Would Work Like This
When you’re a kid, friendship is almost effortless.
You go to school.
You sit next to the same people every day.
You have recess.
Gym class.
Birthday parties.
Summer camp.
If another kid likes the same game you do, congratulations. You have a new friend.
Then something changes.
Nobody really warns you about it.
You graduate.
People move away.
Jobs become demanding.
Relationships become more serious.
Some friends start families.
Others travel constantly for work.
One day you realize it’s somehow been eight months since you’ve seen someone you genuinely care about.
Not because you had a falling out.
Not because either of you stopped trying.
Life simply became…busy.
I don’t think that’s unusual anymore.
In fact, I think it’s become the default.
One thing I’ve noticed over the years is that almost every adult I meet falls into one of two groups.
The first group says,
“I wish I had more friends.”
The second says,
“I have great friends. I just wish we actually saw each other more.”
Those sound like different problems.
I don’t think they are.
The Calendar Is Your Biggest Enemy
People often assume loneliness comes from not knowing enough people.
Sometimes that’s true.
More often, I think it comes from something much simpler.
Nothing is actually on the calendar.
Think about how many conversations you’ve had that ended with…
“We should definitely do this again.”
“Let’s grab dinner soon.”
“We need to plan something.”
Everyone means it.
Nobody opens their calendar.
A month goes by.
Then another.
Eventually someone sends another message.
“Sorry! Life has been crazy.”
They’re telling the truth.
Life really has been crazy.
The problem is that “when things slow down” almost never arrives.
If you’re waiting until everyone suddenly has free time, you’re probably going to be waiting forever.
The happiest groups I’ve seen over the years don’t have more free time than everyone else.
They simply protect it.
Wednesday belongs to volleyball.
Thursday is trivia.
The first Saturday of every month is poker night.
The second Sunday is brunch.
It isn’t complicated.
They’ve simply made the decision once instead of making it every week.
The Best Social Advice I Can Give You
After watching more than 130,000 people come through S3 over the years, if I could give only one piece of advice, it would be this.
Stop trying to find time for your friends.
Instead…
Create traditions.
Those sound similar.
They’re completely different.
Finding time depends on everyone’s schedule magically lining up.
Traditions don’t.
Traditions become part of your schedule.
Nobody asks,
“Are we doing volleyball this week?”
Of course they are.
It’s Wednesday.
Nobody wonders if the fantasy football draft is happening.
It’s been happening every August for ten years.
Nobody asks if the annual tubing trip is still on.
People start requesting vacation days months ahead of time.
The tradition becomes bigger than the activity itself.
That’s what you’re really creating.
Not another thing to do.
Something people start organizing the rest of their lives around.
The Biggest Myth About Building a Social Life
I think social media accidentally convinced us that having a great social life means constantly doing exciting things.
Flying somewhere.
Going to huge parties.
Taking incredible vacations.
Being surrounded by dozens of people every weekend.
That’s not what I’ve observed.
Honestly?
The happiest people I’ve met usually live surprisingly ordinary lives.
They just do ordinary things…
With people they enjoy.
They have dinner together.
They play softball.
They grab tacos after bowling.
They go to neighborhood festivals.
They try a new restaurant every month.
Someone hosts game night.
Someone else invites everyone over to watch football.
None of those things would look particularly impressive on Instagram.
But that’s not the point.
The point is consistency.
Happiness usually isn’t built from a handful of unforgettable vacations.
It’s built from hundreds of ordinary Tuesday nights that slowly become your favorite memories.
Why Some Friend Groups Stay Close for Decades
Have you ever noticed that some groups seem to stay close forever?
They graduate.
They get married.
People move to different neighborhoods.
Jobs change.
Life changes.
Yet somehow they’re still together.
I used to assume they were just lucky.
Now I think they’re intentional.
Somewhere along the way, they stopped relying on chance.
Instead, they built traditions.
Maybe they golf every spring.
Maybe they have a standing ski trip every winter.
Maybe they’re on the same kickball team every summer.
Maybe they celebrate everyone’s birthday together.
The activity almost doesn’t matter.
The commitment does.
Because every recurring activity quietly answers one question that destroys so many adult friendships.
“When are we going to see each other again?”
When the answer is already sitting on the calendar, friendships become much easier to maintain.
So…What Should You Actually Do?
At this point you might be thinking,
“Okay, I get it. I need more recurring activities. But what should those activities actually be?”
The honest answer?
There isn’t one right answer.
If someone tells you that everyone should join a running club, they’re wrong.
If someone says sports leagues are the only way to make friends, they’re wrong too.
The best activity is the one you’ll actually keep showing up for.
That’s much more important than choosing the “perfect” activity.
I’ve watched people build lifelong friendships through kickball.
I’ve watched it happen over trivia.
I’ve seen people who met through volunteer groups become inseparable.
I’ve watched coworkers turn into weekend friends because someone invited everyone to a bowling league.
The common thread was never the activity.
It was the consistency.
Still, after almost two decades of watching adults build friendships, there are certain kinds of activities that seem to work better than others.
Not because they’re more fun.
Because they’re built around seeing the same people over and over again.
The Three Ingredients Every Great Activity Has
This might be the single most useful thing I’ve learned.
The activities that consistently create real friendships usually share three characteristics.
If you’re trying to decide whether something is worth joining, ask yourself these three questions.
-
Will I See the Same People Again?
This is the biggest one.
Friendships almost never happen because of one amazing conversation.
They happen because of twenty completely ordinary ones.
The first week, you learn someone’s name.
The second week, you remember what they do for work.
A few weeks later, you’re joking about something that happened the previous week.
Eventually, you stop thinking of them as “that person from volleyball.”
They’re just your friend.
That’s why recurring activities almost always beat one-time events.
One-night events are fun.
Recurring events build relationships.
-
Does the Activity Give You Something to Talk About?
Have you ever walked into a networking event?
You know the kind.
Everyone’s standing around holding a drink.
Looking at their phone.
Pretending to be interested in the appetizers.
Trying to figure out who they’re supposed to talk to.
It can be exhausting.
Now compare that to trying to solve a trivia question together.
Playing a softball game.
Taking a cooking class.
Volunteering.
Nobody has to invent conversation.
You’re already sharing an experience.
Ironically, the less pressure there is to socialize…
The easier socializing becomes.
-
Are People There Because They Want To Be?
This one gets overlooked all the time.
Think about your workplace.
You might have wonderful coworkers.
But everyone is there because they have to be.
The same is true on a train.
Or standing in line at the grocery store.
Or waiting at the DMV.
Those aren’t places people show up hoping to make new friends.
Now think about someone who signs up for a volleyball league.
Or a photography class.
Or a neighborhood cleanup.
Or a weekly trivia team.
They made a choice.
They wanted to leave the house.
They wanted to try something.
They were open to meeting people.
You’re starting from a completely different place.
That doesn’t guarantee friendship.
But it dramatically increases the chances.
My Favorite Kinds of Activities in Chicago
Chicago is one of those rare cities where you could probably try something new every weekend for years and still have plenty left on your list.
That’s one of the reasons I love living here.
There are incredible restaurants.
World-class museums.
Comedy clubs.
Professional sports.
Neighborhood festivals almost every weekend during the summer.
Beautiful parks.
The lakefront.
Street fairs.
Live music.
Food festivals.
Farmers markets.
Almost every hobby you can imagine has a community somewhere in the city.
The challenge isn’t finding something to do.
The challenge is choosing something you’ll actually keep doing.
Here are the activities I tend to recommend most often.
Recreational Sports Leagues
Let’s get the obvious one out of the way.
Yes, I organize sports leagues.
So of course I think they’re a great option.
But hopefully by now you’ve noticed something.
I haven’t spent this entire article trying to convince you to play kickball.
That’s because sports themselves aren’t what make leagues valuable.
It’s everything wrapped around them.
You have a scheduled reason to see the same people every week.
You naturally work together.
You celebrate wins.
You laugh at mistakes.
You grab dinner afterward.
Week after week, strangers slowly become familiar faces.
Then teammates.
Then friends.
Some of the strongest friendships I’ve watched over the years started with two people who happened to end up wearing the same team shirt.
Not because either of them was looking for a best friend.
Because they kept showing up.
Trivia Nights
Trivia has a lot in common with recreational sports.
You’re working toward something together.
Everyone contributes differently.
Someone always knows the obscure movie question.
Someone else somehow remembers every world capital.
Even if you finish near the bottom, you’ll probably spend the next hour arguing about the answers over food.
That’s a successful night.
Neighborhood Festivals
This is one thing Chicago does better than almost anywhere.
Every neighborhood seems to have its own personality.
One weekend you’re eating amazing Greek food.
The next you’re listening to live jazz.
A few weeks later you’re discovering a neighborhood you’ve somehow never explored before.
You don’t have to spend much money.
You don’t need a detailed itinerary.
You just need a couple of people to experience it with.
Volunteer Opportunities
One thing I’ve always admired about volunteer groups is that everyone arrives with the same mindset.
They’re there because they want to contribute.
That immediately changes the atmosphere.
Working toward a common goal has a way of bringing people together quickly.
Even if you only volunteer once a month, it can become another recurring tradition that adds meaningful relationships to your life.
Classes
Cooking.
Photography.
Pottery.
Dance.
Improvisation.
Language exchanges.
Almost any class that meets over several weeks gives you the same advantage we’ve talked about throughout this guide.
Repeated exposure.
There’s a psychological principle called the mere exposure effect: people tend to become more comfortable with and like things they encounter repeatedly. That doesn’t mean you’ll become close friends with everyone you see every week, but it does explain why recurring activities often feel so much more welcoming over time than one-off events.
That’s why I always tell people not to worry so much about choosing the “perfect” hobby.
Choose something that sounds interesting.
Then keep showing up.
People Join for Different Reasons
One thing that still surprises me after all these years is how different people’s reasons are for signing up.
On the surface, everyone joins a recreational sports league.
But underneath, they’re often looking for completely different things.
Some people are looking for new connections.
Others are trying to protect the friendships they already have.
And plenty of teams start at work, where coworkers want a better way to spend time together outside the office.
The reasons are different, but the thing that makes all of them work is the same: people keep showing up.
Group One: “I Want to Meet New People.”
Maybe you just moved to Chicago.
Maybe your college friends are scattered across the country now.
Maybe you work remotely and miss being around people.
Maybe you went through a breakup and realized most of your social life revolved around one relationship.
Or maybe you simply woke up one day and thought,
“I need to get out of the house more.”
If that’s you, I have some good news.
You’re far from alone.
Every season, we have hundreds of people register by themselves.
And almost every one of them has the same concern before their first game.
“What if everyone else already knows each other?”
The answer?
Some teams do.
Many don’t.
In fact, every season we create teams made up entirely of people who registered on their own.
Nobody knows anyone.
Everyone is starting from exactly the same place.
And something interesting happens.
The first week feels a little awkward.
By the second week people remember names.
By the third week they’re laughing about something that happened during the previous game.
A few weeks later, someone suggests grabbing dinner afterward.
Someone else starts a group chat.
Before long, nobody really remembers which week stopped feeling awkward.
They just know they’re looking forward to next Wednesday.
I’ve watched that happen thousands of times.
It never gets old.
Group Two: “I Already Have Friends. I Just Miss Them.”
This group doesn’t get talked about nearly enough.
I actually think it describes more adults than the first one.
These people aren’t lonely.
They’re busy.
They have wonderful friends.
People they genuinely love spending time with.
The problem is that everyone’s life keeps pulling in different directions.
One person lives in the suburbs.
Another just had a baby.
Someone else changed jobs.
Another friend travels every other week.
Everyone still wants to get together.
Nobody can figure out when.
Sound familiar?
That isn’t a small part of S3. We get lots of full teams register to play in our leagues.
Usually one person steps up as captain, reserves the team spot with a deposit, and gathers the roster.
Those teams are the backbone of our leagues.
Sometimes they’re lifelong friends.
Sometimes they’re neighbors.
Sometimes they’re coworkers.
They’re not joining because they need strangers to meet.
They’re joining because they want a reason to keep doing something together.
This is one of the reasons I believe so strongly in recurring activities.
When your friend group joins a league together, something subtle changes.
You’re no longer trying to schedule time together.
You’ve already scheduled it.
Every Wednesday.
Every Thursday.
Whatever night you play becomes your night.
I’ve watched friend groups who expected to play one season end up making it part of their lives for years.
Some teams have been playing together for so long that new spouses have joined.
Coworkers have come and gone.
People have moved across the city.
Kids have been born.
The roster slowly changes.
The tradition doesn’t.
Honestly, I think that’s beautiful.
Group Three: “We Want Our Coworkers to Actually Know Each Other.”
There’s another version of this that I think companies often overlook.
People can work together every day and still barely know each other outside of meetings and deadlines.
That’s especially true when people are spread across departments or only see each other in the office a few days a week.
A one-night company outing can be fun.
But then it’s over.
A league gives coworkers something different.
For several weeks, they have a reason to leave work behind, put on the same team shirt, laugh together, compete a little, and spend time together as people instead of job titles.
Some companies enter an entire team. Others have a few employees start it and invite coworkers to fill out the roster.
Either way, the same thing happens that happens with every other recurring group.
They build shared stories.
The funny play everyone talks about the next morning.
The teammate nobody knew was secretly great at volleyball.
The post-game dinner that lasts longer than expected.
That kind of team building doesn’t feel like a team-building exercise.
It just feels like people having fun together.
And in my experience, that’s usually when the bonding actually happens.
The Best Teams Usually Aren’t the Best Teams
This probably sounds strange coming from someone who organizes leagues.
But the teams that seem to have the most fun are rarely the ones winning championships.
They’re the ones laughing the most.
They’re the teams with the ridiculous names.
The matching shirts.
The running jokes.
The teammate who always forgets their glove.
The captain who sends unnecessarily enthusiastic reminder texts every Tuesday afternoon.
The tradition of getting tacos after every game.
The annual photo where everyone somehow makes the exact same goofy face.
Those little rituals become part of the team’s identity.
Years later, people won’t remember whether they finished 6-2 or 4-4.
They’ll remember laughing so hard they could barely breathe after someone accidentally kicked the ball into the dugout instead of the field.
That’s the stuff that sticks.
My Favorite Moment Every Season
People sometimes ask me what my favorite sport is.
Honestly, I don’t have a good answer.
Because my favorite part of the night usually happens after the games are over.
It’s when I’m walking through the sponsor bar and I see teams that met only a few weeks earlier sitting around the same table.
Someone’s telling a story.
Someone else is laughing so hard they’re crying.
A few people are introducing teammates to friends who weren’t even playing that night.
You can almost watch relationships forming in real time.
That’s when I quietly think,
“This is why we do this.”
Not because someone won.
Not because the schedule ran perfectly.
Not because every game started exactly on time.
Because people who were strangers not long ago are now making plans for next weekend.
That’s always been the goal.
The sports just happen to be the vehicle.
Here’s Something Most Businesses Never Get to See
This is one of the biggest privileges of running S3 for so many years.
Most businesses get one interaction with their customers.
A restaurant serves dinner.
A movie theater sells a ticket.
A store completes a sale.
Then everyone goes home.
We’re lucky.
We get to watch stories unfold over months…
Sometimes years.
You start recognizing faces.
You see someone bring a coworker the next season.
Then that coworker starts a team.
A few years later you hear two teammates got engaged.
Then someone says,
“Hey, remember them? They just had a baby.”
Every once in a while, a former player stops by with their kids and says,
“This is where we met.”
I don’t think about the registration anymore.
I think about all the Wednesdays in between.
Because that’s where life actually happened.
Why We Built S3 This Way
By now, you’ve probably noticed something.
I’ve spent a lot more time talking about people than sports.
That’s intentional.
Because when I started S3 back in 2009, I wasn’t trying to create the most competitive recreational leagues in Chicago.
I was trying to create leagues that people would actually look forward to every week.
Those aren’t always the same thing.
From the beginning, we made a few decisions that have shaped everything we’ve done.
Some probably seemed small at the time.
Looking back, I think they made all the difference.
We Wanted Beginners to Feel Comfortable
One of the quickest ways to ruin a recreational league is to make new players feel like they don’t belong.
Everyone starts somewhere.
Most people aren’t former college athletes.
They’re accountants.
Teachers.
Engineers.
Nurses.
Marketing professionals.
Software developers.
Salespeople.
Parents.
Recent college graduates.
People who haven’t played since middle school.
And honestly?
That’s exactly who recreational leagues should be for.
One of my favorite moments every season is watching someone apologize after making a mistake.
Almost without fail, three teammates immediately say something like,
“Don’t worry about it. We’ve all done that.”
That’s the culture we always hoped to create.
Because once people stop worrying about looking silly, they usually start having a lot more fun.
We Wanted Full Teams and Individuals to Feel Equally Welcome
This was important to us from the very beginning.
Some people already have a great group of friends.
Fantastic.
Bring them.
Other people don’t know a single person.
They’re taking a chance by signing up alone.
They deserve to feel just as welcome.
That’s why we’ve always loved building free agent teams.
There’s something really rewarding about watching ten complete strangers walk onto a field during week one…
…and walk off the field after the championship game feeling like they’ve known each other for years.
Not every team becomes lifelong friends.
Some do.
Every season it happens.
And every season it’s still fun to watch.
We Never Wanted the Night to End When the Game Did
One of the earliest decisions we made had nothing to do with sports.
It had to do with what happened afterward.
If everyone gets in their car immediately after the final whistle…
The opportunity for friendships to grow is pretty limited.
But if teams head to the same sponsor bar…
Something different happens.
The game becomes the beginning of the evening instead of the end.
People replay the funniest moments.
Someone orders food.
Another teammate introduces a friend who wasn’t playing that night.
Conversations that started on the field continue over burgers, tacos, wings, or whatever everyone feels like eating.
Sometimes those conversations last longer than the game itself.
That’s not an accident.
We wanted to create opportunities for people to linger.
Friendships usually aren’t built during a seven-inning softball game.
They’re built in the conversations that happen afterward.
Winning Was Never the Point
Now, don’t get me wrong.
People like to win.
I do too.
Competition makes games exciting.
Close games are fun.
Playoffs are fun.
Championship nights are fun.
But if someone asks me ten years from now what I hope they remember about S3…
I hope the answer has nothing to do with trophies.
I hope they remember the people.
The laughs.
The traditions.
The feeling of looking forward to Wednesday all week.
The teammate who somehow forgot the schedule every season but always made everyone smile when they finally arrived.
The post-game dinners.
The inside jokes that made absolutely no sense to anyone else.
Those are the victories that actually last.
Something Unexpected Happened
When I started S3, I thought we were organizing leagues.
What I didn’t realize was that we’d eventually become part of people’s stories.
Over the years, we’ve watched friendships begin.
Relationships grow.
Teams stay together for years.
People move away and still come back for reunions.
We’ve celebrated proposals.
Weddings.
Babies.
Career changes.
Even retirement parties where half the guests first met through a league.
Every now and then someone sends us a message that says something like,
“I almost didn’t sign up because I didn’t know anyone.”
Or,
“I’m so glad my friend convinced me to join.”
Those messages never get old.
Not because they make us feel successful.
Because they remind us why this matters.
Life moves quickly.
If we can help make a few years of someone’s life a little more connected, a little more active, and a little more fun…
That’s something worth being proud of.
If You’re Waiting for the Perfect Time…
Can I offer one piece of advice?
Stop waiting.
I don’t mean quit your job.
Or fill every night of your calendar.
I just mean stop assuming there will be a future season of life when everything slows down.
Because in my experience, it rarely does.
There’s always another project.
Another deadline.
Another trip.
Another birthday party.
Another reason to say,
“Maybe next month.”
The people I know with the richest social lives aren’t the ones with the most free time.
They’re the ones who decide that spending time with people they care about deserves a permanent place on the calendar.
Everything else gets scheduled around that.
Not the other way around.
One Day, These Will Be the Good Old Days
There’s something funny about memories.
We almost never realize we’re making them while they’re happening.
At the time, it just feels like another Wednesday.
Another Thursday.
Another ordinary week.
You rush out of work.
You throw your glove in the car.
You grab dinner afterward.
You laugh about something ridiculous that happened during the game.
You head home.
Nothing about the evening feels extraordinary.
Then ten years go by.
Someone sends an old team photo into the group chat.
Suddenly everyone starts remembering.
The team name.
The shirts everyone thought were hilarious.
The teammate who somehow managed to be late every single week.
The inside joke nobody else would understand.
The restaurant where everyone always ended up after games.
The championship nobody remembers…
…and the night everyone stayed out talking until midnight, which everyone does.
Funny how that works.
The things we think will matter usually fade.
The things we never expected to remember somehow become the stories we tell forever.
I Hope This Guide Changes One Thing
If you’ve made it this far, I hope you don’t remember every piece of advice in this article.
Honestly, I hope you forget most of it.
I hope you remember one simple idea.
Don’t wait for life to slow down before making time for people.
It probably won’t.
Instead…
Create something to look forward to.
Protect it.
Make it part of your routine.
Maybe that’s a weekly softball game.
Maybe it’s trivia.
Maybe it’s a monthly dinner.
Maybe it’s finally texting that group of friends you’ve been meaning to see for months.
The activity doesn’t matter nearly as much as the consistency.
Your future self won’t remember every email you answered.
Or every meeting you attended.
You’ll remember the people.
A Small Challenge
Before you close this page…
Send one text.
That’s it.
One.
Not tomorrow.
Not next week.
Right now.
Maybe it says,
“Who’s free for dinner next week?”
Maybe it’s,
“Want to start a trivia team?”
Maybe it’s,
“I think we should finally sign up for something together.”
Or maybe it’s just,
“It’s been too long. Let’s put something on the calendar.”
Don’t overthink it.
Someone has to send the first message.
It might as well be you.
If We Ever Meet…
Maybe you’ll never play in an S3 League.
That’s okay.
I genuinely hope you build the kind of social life you’re looking for anyway.
Maybe you’ll find it through volunteering.
Maybe through a running club.
Maybe through your church.
Maybe through a neighborhood organization.
Maybe through something that isn’t mentioned anywhere in this guide.
If that happens…
Then this article did its job.
Of course, if you’re looking for a fun, welcoming, low-pressure way to spend more time with your friends or meet some new ones, I’d love for you to check out what we’re doing at S3.
That’s why we built it.
Not because the world needed another sports league.
Because I believe adults need more reasons to spend time together.
That’s all we’ve ever been trying to create.
One Last Thought
After all these years, I think I’ve finally figured out what people are really looking for.
They’re not looking for kickball.
Or volleyball.
Or bowling.
Or trivia.
Or tacos after the game.
Not really.
They’re looking for belonging.
For people who are happy to see them.
For a reason to leave the house on a Wednesday.
For a group chat that makes them laugh.
For friendships that don’t slowly disappear because everyone got busy.
For stories they’ll still be telling years from now.
Sports just happen to be one of the ways those things begin.
I hope you find yours.
And maybe…
I’ll see you out there.