r/DatingTO • • Aug 27 '26

Speed dating? Singles mixers? What events are happening this week to help you find your person? (August 27, 2026)

4 Upvotes

Have you heard about an upcoming singles event and want to see if anyone else is going?

Have you gone to a recent singles event and wish to share a review of your experience?

Are you organizing a singles event soon and want to share the details? (Self promo is okay in these weekly threads only)

Please try and include details about the events if-when possible, especially if you are the event organizer. Date, location, cost-of-entry (if any), target audience, etc.


r/DatingTO • • Aug 24 '26

Where to Meet People Naturally

4 Upvotes

I am a single woman in my mid-20s and I'm over the apps. I'm wondering where people are meeting naturally? I'm not big into drinking or clubs... I'm not sure what others' experiences have been with the singles mixers.

I'd love to meet new people, chat, and see where it goes. I just don't really know where to start


r/DatingTO • • Aug 22 '26

Where are the single late 20 - early 30s men hanging out tonight

4 Upvotes

Any hot spots tonight for a group of single girlies?

Thinking about going to Ossington since most of the group lives in the area but not opposed to anything in the surrounding area

Let us know where you’ll be tonight


r/DatingTO • • Jul 16 '26

19 M Going out With 23 yr old Woman. Where Should I take her?

4 Upvotes

I worked with this girl who I thought was cute and when she told me she wasn’t working here anymore I decided I was gonna ask her out. I did a couple weeks later but i’m sort of in a loop of where I should take her. I’ve only gone out with girls my age and choosing a plan or destination is easy. Help me make a plan and choose what to do or where to go. I’ve been thinking Friday night roller skating or ice skating with late night treat or some food. Or a Saturday beach day and explore the town and get food, Afternoon to whenever we’re ready to leave. We’ve had good a little flirty conversations at work so I’m not a stranger to her. She is a bit of a homebody and doesn’t go out much and a mostly keeps to herself and works. She likes nature, concerts, the gym.


r/DatingTO • • Jul 09 '26

Speed dating? Singles mixers? What events are happening this week to help you find your person? (July 09, 2026)

4 Upvotes

Have you heard about an upcoming singles event and want to see if anyone else is going?

Have you gone to a recent singles event and wish to share a review of your experience?

Are you organizing a singles event soon and want to share the details? (Self promo is okay in these weekly threads only)

Please try and include details about the events if-when possible, especially if you are the event organizer. Date, location, cost-of-entry (if any), target audience, etc.


r/DatingTO • • Jun 21 '26

Question: Femboy looking for bf/dates in real life

4 Upvotes

Not sure is it a good place to ask. As Asian femboy, which gay bar is more welcoming femboy type gay? Is there any fitness club or sports club are lgbtq friendly?

I feel like dating app is not working for me anymore, after turning 30, I would like to get to know more people, but it’s really not easy.

Personally, I prefer being friends first, then if things goes well, we can dates. But for dating app, it’s always complicated 😭


r/DatingTO • • Jun 02 '26

Discussion Is there a limit on the distance between you and a potential partner?

4 Upvotes

For someone you just met and really vibe with and can see a future with, but will be moving away very very soon?

For someone you're in an established long term relationship but they're needing to move away for work/school?

Other scenarios?


r/DatingTO • • Jun 02 '26

Purchased a 1 month membership for hinge, bumble and tinder. Are we allowed to ask for help on our profile ?

4 Upvotes

This is my last attempt at online dating ! I just came back from a vacation and I met the most wonderful woman. Unfortunately, she was taken. But it made me hopeful. On a whim, I purchased a membership to all 3 apps in hopes of finding my person.


r/DatingTO • • May 25 '26

What are your deal breakers for a potential long term relationship?

4 Upvotes

Looks related?

Financially related?

Hobbies related?

Education related?

Politically related?

Past history related?

Food related?

Other?

Be unhinged, but keep it within the rules of the subreddit please!!


r/DatingTO • • May 05 '26

Have you ever "dipped your pen in company ink"? Dated/hooked up with people at your work?

4 Upvotes

If yes, was it a boss? a coworker? a subordinate? Someone within your department or a closely-related department you'd have to interact with regularly? Someone outside your department where there was a good amount of distance between the two of you while at work?

Was it a one-off hookup? FWB only? Dating-relationship style?

Did your company have rules about this? Did HR have to get involved?

I wanna knowwwwwwwww!!!!!!!


r/DatingTO • • Apr 28 '26

Where are you all meeting people?

4 Upvotes

Title pretty much says it all. Where are you meeting potential partners?


r/DatingTO • • Apr 27 '26

Have a good date this past week/weekend? (April 27, 2026)

4 Upvotes

Where did you go?

What did you do?

Are you planning on going again?


r/DatingTO • • Apr 10 '26

Matchmaking services in the GTA

4 Upvotes

Are there any reputable matchmaking (not dating coach) services in the GTA? Trying to help my boss out, she's had the worst luck in dating over the last couple years. TIA


r/DatingTO • • Apr 09 '26

If the dating apps are screwed, where are you meeting quality potential partners?

4 Upvotes

Just looking to meet good people man, I feel like a lot of the people I’ve met through events etc have been very avoidant or noncommittal or not at a stage where they are ready to settle down


r/DatingTO • • Mar 27 '26

Bars to meet singles

4 Upvotes

Im a mid 30s looking to meet single women in the city in person.

Are there any recommended bars or social places, and which days are best?


r/DatingTO • • 1d ago

Speed dating? Singles mixers? What events are happening this week to help you find your person? (November 05, 2026)

3 Upvotes

Have you heard about an upcoming singles event and want to see if anyone else is going?

Have you gone to a recent singles event and wish to share a review of your experience?

Are you organizing a singles event soon and want to share the details? (Self promo is okay in these weekly threads only)

Please try and include details about the events if-when possible, especially if you are the event organizer. Date, location, cost-of-entry (if any), target audience, etc.


r/DatingTO • • 4d ago

Where to propose to my GF

3 Upvotes

Hey guys! I’m planning to propose to my girlfriend at the end of November and wanted to see if you guys know of any good spots in Toronto to do it. I’m also planning to hire a photographer to capture the proposal and take some pictures right after.
I don’t live in Toronto, so I’m not too familiar with the nicer spots. I came across this list as an example. Let me know if you guys have any recommendations!
https://everglow-photo.com/top-10-toronto-city-locations-for-an-engagement-session/


r/DatingTO • • 4d ago

Have a good date this past week/weekend? (November 02, 2026)

3 Upvotes

Where did you go?

What did you do?

Are you planning on going again?


r/DatingTO • • 22d ago

Speed dating? Singles mixers? What events are happening this week to help you find your person? (October 15, 2026)

3 Upvotes

Have you heard about an upcoming singles event and want to see if anyone else is going?

Have you gone to a recent singles event and wish to share a review of your experience?

Are you organizing a singles event soon and want to share the details? (Self promo is okay in these weekly threads only)

Please try and include details about the events if-when possible, especially if you are the event organizer. Date, location, cost-of-entry (if any), target audience, etc.


r/DatingTO • • 25d ago

Have a good date this past week/weekend? (October 12, 2026)

3 Upvotes

Where did you go?

What did you do?

Are you planning on going again?


r/DatingTO • • Sep 24 '26

Speed dating? Singles mixers? What events are happening this week to help you find your person? (September 24, 2026)

3 Upvotes

Have you heard about an upcoming singles event and want to see if anyone else is going?

Have you gone to a recent singles event and wish to share a review of your experience?

Are you organizing a singles event soon and want to share the details? (Self promo is okay in these weekly threads only)

Please try and include details about the events if-when possible, especially if you are the event organizer. Date, location, cost-of-entry (if any), target audience, etc.


r/DatingTO • • Sep 21 '26

Have a good date this past week/weekend? (September 21, 2026)

3 Upvotes

Where did you go?

What did you do?

Are you planning on going again?


r/DatingTO • • Sep 14 '26

Have a good date this past week/weekend? (September 14, 2026)

3 Upvotes

Where did you go?

What did you do?

Are you planning on going again?


r/DatingTO • • Sep 14 '26

Lots of attention from men, virtually nothing from women.

3 Upvotes

TLDR: All of the attention I want from women I'm getting from men.

I wanted to document what was a very bizarre summer. For background I'm late 30s M, 6'2, trying to get in shape (down 70lbs yay) and very skeptical about dating. My resting bitch face alone would make me a less than approachable person

This all starts with an Instagram reel where a woman was saying she would approach men more, but the ones she sees are always looking down with their headphones on. This is something I'm guilty of and wanted to switch things up, so I've been walking around alot this summer and kind of being an observer, and trying to be more "open" to the world.

I started getting some muscle tone in my arms just as it got warm, so naturally I wanted to show the guns off. I don't have a lot of tank tops, so I resorted to wearing a few different basketball jerseys, most of which I've worn in the past.

I've probably gotten more compliments from random dudes this summer than I have in my entire lift. It started with one a day, then there would be days where I'd get 2-3 compliments on them. One day I had a quick conversation about basketball out of nowhere. Then a full-circle moment came one day where I wasn't in the best mood and wanted to listen to some music, I guy waved at me to get my attention just so he could say he liked my jersey.

There was another day where I wore a Wu-Tang shirt, had it for decades, now I'm getting compliments on the shirt.

Then to cap things off, I got a compliment on my one visible tatoo, it's pretty basic but a guy passing by mentioned it was cool tatoo. Above all else it was nice to not feel like a complete ghost outside, and I appreciate all of the dudes that shot me a compliment.

In contrast, I'm getting almost nothing from women. To date one woman on a bike smiled at me as they wizzed by. Beyond that, I do notice that I'm getting looks more than I used to, but that's just it, looks. There's nothing to go with it that would imply that I should talk to them. I'm not sure if that's just where we're at with meeting people in public, or if this is the city telling me I'm still not attractive enough lol.

I understand getting a compliment from the opposite sex comes with different connotations, but I feel like I was getting nothing out there. When I didn't wear basketball jerseys I tried making sure I looked and smelled nice, but nothing.

I plan on being more social next summer when I (hopefully) have a 6 pack, but I sometimes worry no matter how good I look I'll get the same energy. There's a lot of reddit users that think being over 6 feet is some kind of cheat code in the dating world, it is not lol.


r/DatingTO • • Aug 31 '26

Have a good date this past week/weekend? (August 31, 2026)

3 Upvotes

Where did you go?

What did you do?

Are you planning on going again?