Out of your head, into the world
Structured social events where interaction feels natural.
No icebreakers or spotlights.
Why our events feel easier
Our events are built around a shared objective, which makes it easier to talk and take part.
No age limits.
No conversation prompts.
No pressure to perform.
A relaxed cocktail-style social that lets people mingle in a structured environment. The magic is in the cards.
For solo guests, couples, and friend groups.
🎲Next Cards event: April 25, 2026
Our softball events give you a reason to get outside, move your body, and spend time with others. Our two-event format ensures everyone has a place on the field, regardless of experience level.
Open to solo players, couples, and friend groups.
Next softball event: May 17, 2026
How would you like to head out?
Is this for you?
Head Out Toronto is for adults who want an easy, comfortable way to enjoy time with others.
We are especially popular with people in their 30’s and 40’s (and up!) who want social plans that fit where they are in life.
Some are getting back into social life, some are starting a new chapter, and others are just tired of the usual options. We design events with this crowd in mind.
Our events are built around simple activities that give people an easy way to talk to each other.
Adult social life doesn’t organize itself anymore, so we do.
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!