Out of your head, into the world
Head Out Toronto runs structured, in-person events designed to make it easier to show up and connect.
No forced icebreakers or spotlights.
Every event is built to remove social friction, so interactions feel natural instead of forced.
It’s in the Cards feels like a cocktail night built around a simple trading game.
In Play and Starter Series feel like a relaxed block party built around softball.
Choose Your Vibe:
It’s in the Cards
The social night that breaks the ice for you.
The Setup: You’re handed a random card to a local cafe or shop at check-in.
The Game: Trade with other guests to get the prize you want. About 1 in 3 people leave with a real gift card.
The Relief: No “cold” approaches. The game gives you a natural reason to talk to anyone in the room.
In Play - Softball
The "team for a day" social that feels like a block party.
Sign up solo, as a couple, or with friends. We’ll place you on a team.
Play two games at Coronation Park, eat BBQ, and spend the afternoon meeting your neighbours.
Scores are kept, but the vibe stays friendly.
Starter Series - Intro to Softball
The "I’ve never played" solution.
For anyone new to the game, or thinks they’re bad at sports.
We go over the basics, then play a casual beginner-only game.
No “pros” allowed. Focus on meeting people and enjoying the fresh air instead of worrying about your skill level. BBQ included.
Who is Head Out Toronto for?
Adult social life doesn’t organize itself anymore, so we do it.
We’ve become the go-to for people in their 30s, 40s (and up!) who are looking for social plans that actually fit their life.
The “New Chapter” Crowd: New to the city, starting over, or just ready to meet some new people.
Couples: A built-in plan for your next outing. Bond as teammates on the field or enjoy a night out where it’s actually easy to talk to other couples.
The Solo Guest: Our events are designed for people coming on their own. Over 60% of our guests show up solo.
The 30s, 40s, and Up: For adults who want social plans that actually fit where they are in life
What to expect at our events
• A simple check-in and quick overview when you arrive
• A schedule shared in advance
• A clear start and end time
• Space to step aside and rejoin when you’re ready
You’re part of something that’s organized, but you take part in a way that feels right to you.
Ready to head out?
Find an event that fits your style.
Testimonials
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"I’ve played softball before but felt like I actually learned the sport this time. Meeting new people and getting team bonding and advice was awesome."
- Nina S., In Play (Softball)
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"The bracelets were a nice way to find teams. Food was good, staff were friendly, and the whole event was well run and organized!"
- Jasdeep K., In Play (Softball)
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"It was a fun and unique idea, I’d definitely be interested in another It's in the Cards event!"
- Sam, It’s in the Cards
FAQ
What kind of events do you run?
We currently run three types of events you can join: our casual softball events called In Play or Starter Series (for beginners), and our cocktail-style card nights called It’s in the Cards.
Do I need to come with friends?
No, our events are designed with solo guests in mind. Of course, couples and friend groups are welcome too.
Is this like speed dating, networking, or a singles event?
No. Our events aren’t designed for dating or networking, but we love when connections happen. The main purpose of our events is to give people an easy, comfortable way to enjoy time with others.
What ages usually attend?
Most people are in their late 20s to 40s. We welcome all ages, but our events typically run 19+.
Do I need to be outgoing?
Not at all. These events are designed to work well for introverts as well as extroverts.
What happens when I arrive?
You’ll check in when you arrive, and we’ll help you get settled. Our events usually begin without any big announcements, and there are no icebreakers or forced spotlights on people.
What should I bring?
For It’s in the Cards, just yourself. For In Play and Starter Series softball, bring a glove and a water bottle if you have them. If you don’t have a glove, we can provide one.
What if I feel awkward?
That’s completely normal at the start of any social event. If you ever feel unsure, you can always come to the check-in table or talk to a volunteer.
How do I find out about upcoming events?
We keep our Events page on the website up to date with new listings.
Try These Free Real-World Action Challenges
Free Download: Head Out Action Cards
Real-world mini challenges that get you out of your head and into the world.
Get the full 40-card PDF free and we’ll let you know about future events.
Contact us
Got a question? Want to volunteer, partner with us, or just say hi? We’d love to hear from you!