About us
Remember when school gave us an easy way to meet people?
Friendships happened so naturally. But as adults, that structure disappears.
We're surrounded by people but can go days without actually talking to anyone.
Most of us don't need help socializing. We just need a reason to start.
And that's what Head Out Toronto is.
Head Out Toronto is a group for people in their 30s and 40s+ who want to get out more, meet new people, and actually enjoy doing it.
We create simple, structured social events that make it easy to connect with others, without any pressure or overthinking.
Some events are built around conversation, and some around playing, moving, or being outside.
They make it easy to walk in and feel like you belong.
Most people come on their own. But coming with a friend works too.
Never any icebreakers or unwanted spotlights.
Come alone or with friends.
Upcoming events
3
It’s in the Cards: A Better Way to Meet People (30s & 40s) – Liberty Village
Private event space in Liberty Village, 75 East Liberty St, Toronto, ON, CAA social night where talking to anyone feels easy.
Your friends are great. You just don't see them enough anymore.
This is a place to meet new people without networking, small talk, or having to impress anyone.
Most people come on their own.
How it works
Everyone gets a card tied to a local Toronto spot.You spend the night trading with people for one you want more. That's your reason to walk up to anyone in the room.
Near the end, names are drawn and about 1 in 3 people win the real gift card.
Details
Saturday, April 25 · 7–10 PM
Liberty Village · 75 East Liberty St
Around 60–80 peopleGet your ticket here: https://www.eventbrite.ca/e/1983744005722?aff=oddtdtcreator
16 attendees
Social Softball – In Play (Rec level · 3-Pitch · No Pressure)
Location not specified yetSpend a day outside playing softball, having a drink, and actually enjoying being out with people.
This event is called In Play - a social-first day for people who have played before and understand the rules of the game.
It's 3 pitch format, with teams pitching to their own players.
Teams and game times are set in advance, so you'll know exactly when you're playing. Each team plays two games within a 4-hour window, and you're welcome to hang out at the park as long as you like.
Most people sign up solo or with a friend.
What to expect:
- 2 casual games (50 minutes each)
- Social-first, rec level play
- 3-pitch format
- BBQ lunch
- Team and schedule set in advance
- Self umpired gamesDetails:
Date: Sunday May 17th
Time: Between 10AM - 4PM
Location: Coronation Park, Toronto$30 early bird / $35 regular
Early bird ends May 1st or when spots fillRegister here ($30 early bird ends May 1st): https://www.headouttoronto.ca/registration
New to softball?
Start with our Starter Series instead!2 attendees
Beginner Softball – Starter Series (No Experience Needed)
Location not specified yetNever played softball before? This is where you start!
Register here ($25 early bird ends May 1st): https://www.headouttoronto.ca/registration-1
The Starter Series is a beginner-first session designed to help you learn the game in a relaxed, low-pressure setting.
No experience needed. No expectations.
We’ll walk you through the basics, then get you into a paced, beginner-friendly game so you can actually play without feeling overwhelmed.
We use softer balls and batting tees when needed, so it's easier to get started and build confidence.
Your session takes place within a 3 hour window (morning or afternoon) and you're welcome to hang out at the park before or after.
What to expect:
- 60-minute beginner-friendly tutorial
- 1 paced, beginner friendly game
- Softer balls + optional batting tees
- All equipment provided (bats, balls, gloves available)
- Supportive, low pressure envrionment
- BBQ & drinksDetails:
Date: Sunday May 17th
Time: Between 10AM - 4PM
Location: Coronation Park, TorontoRegister here ($25 early bird ends May 1st): https://www.headouttoronto.ca/registration-1
4 attendees
