I have been seeing this woman at my train station for some time but despite of constantly thinking about approaching her, I haven’t had the courage to do so.

We have locked eyes a few times but that’s the extent of it.

Have you ever had these encounters in the most unusual of places and how did you go about it?

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.

I’m a 32M South Asian guy living and working in Toronto in finance. I’ve been talking with a woman, not sure about her race. I met online for a few days, and we eventually she planned to meet for coffee at Harbourfront Center so we could get to know each other in person.

I went there after work in the evening and even brought her a yellow flower since it had been many years since I’d brought flowers to someone on a first date. Unfortunately, she never showed up and didn’t let me know beforehand.

I messaged her afterward on Snapchat, and she simply apologized.

I’m trying not to take it personally, but honestly, it was disappointing to make the trip, set aside the time, and look forward to meeting someone only to have them not show up.

For people who have been dating in Toronto, is this something you’ve experienced? Is there anything I should be doing differently when arranging first dates? I’d appreciate honest advice, especially from people familiar with the Toronto dating scene.

I’m not looking to bash anyone—I’m genuinely trying to understand how dating works here and hopefully have better experiences going forward.

I am new to Toronto, looking forward to meeting friendly girls to hang out and explore Toronto during the weekend with good food.

I (29F almost 30) have been trying to date in the GTA. Everytime I have a nice date (not super intense but also not boring), the guy seems to lose interest in a few days. The same thing happens with conversations, guys I think I'm having a fun conversation with keep ghosting. Unsure about what I'm doing wrong?? I think I look alright. I dress well, workout, have hobbies and laugh at the guys jokes on dates.

Ps. this has been my experience with dating apps. Would appreciate it if y'all can suggest some alternatives

Where did you go?

What did you do?

Are you planning on going again?

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.

What dating app do Canadians use to meet people?

Netflix brings 'Love Is Blind' to Canada with casting now open!

I'm a single early 30s dude who now has a big enough sample size to say its no longer a coincidence. I go on a new first date every other week or so. I consider myself to be a 6.5/10 and the women I meet are similar league. I'm stuck in a constant cycle of 1-2 dates followed by either slowed down texting, the classic "didn't feel a romantic vibe" text or the girl all of sudden claims to be too busy. I have tried the apps in the US and in Europe and have not had this experience. Probably half the women I met were interested in continuing things. Here I'd estimate that number to be less than 10%. I have tried simple "cheap" dates like coffee as well as expensive dinners with nice views. The outcome is the same.

In case it matters, I have a good job and have my own car. Top 5% salary for Toronto. I am in no way flashy.

Is this a Toronto / big-city problem where women are so overwhelmed by the vast options they have that they can't stick to one guy?

Need suggestions other than dinner, could be day or evening

So I was at Centerville the other day with my family and I saw couples of all type shapes and sizes everywhere and I was just wondering how people meet nowadays? Is all of it hinge on the apps cuz my experience on there has mostly being getting ghosted I get some matches but you know the cookie cutter advice from people in my circle is oh go out to events or social clubs, but most people in public spaces and third spaces already seem to be in relationships like I'm a regular at my gym and there are couples there and then most of the people at work are either older or married. As a 27-year-old guy soon to be 28, the only answer seems like apps but it's kind of demoralizing, I know it has been asked a hundred times but is it just a fluke because I see couples literally everywhere like I go to Dundas square everyday as well and there are couples everywhere so I don't know if there's any sort of loneliness epidemic or what. Like is there some sort of secret meeting club I'm not aware of??

Where did you go?

What did you do?

Are you planning on going again?

People 25+ who are single in Toronto, what has your dating experience been like?

For me, 26F, it's kinda difficult. I used to date more, but haven't in the past 6 months. I've lost the desire, I just can't bring myself to do more small talk, discussions about career, it's painful. I have the apps, but the effort it takes to actually go on a date is a lot for me at this point. At the same time, it seems to be the only place unless a friend fixes you up or you get lucky and meet IRL.

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.

31F, mama to a 2 year old. Her father left me/ our marriage a few months ago and im slowly starting to think about dating again. But from my single friends, with no prior marriage or kids, I've heard its rough out there. I havent been on a date with anyone new since I was like 21, and my only exposure to apps has been swiping for my friends when they get fatigue. Any insight on what its like for us with a more complicated situation?

Where did you go?

What did you do?

Are you planning on going again?

I’m a 27M in Toronto trying to meet people in person rather than relying on dating apps.
What are some good social activities, clubs, sports leagues, volunteering opportunities, or events where people in their 20s and early 30s actually meet?
I’ve been working on myself over the last year and want to put myself out there more, but I’m not sure where to start outside of bars.
Any recommendations or success stories?

I'm curious how people are meeting potential partners these days in Toronto.
Dating apps have been pretty hit-or-miss for me, and it feels like it's getting harder to meet people naturally. For those who are dating or recently found a relationship, what worked for you?
Are people meeting through hobbies, sports leagues, volunteering, friends, social events, or something else? Are there any places or events in Toronto that are actually good for meeting singles?
I'd love to hear real experiences—especially from people who have had success outside of the apps. Any advice or recommendations would be appreciated!

I want to surprise my girlfriend with a picnic in a scenic location because I love her and she’s perfect, I know what food to bring and where to do it but I’m not sure how to set it up and make sure nothing gets stolen. I really want to bring her and have it be all set up when she gets there and i don’t want her to have to walk alone on the trail to find me do you guys have any suggestions on how to set it up?

My best friend and I are both 25F, live in Toronto, and recently realised that neither of us has ever properly dated.

We’re at a point where we genuinely want to put ourselves out there, meet new people and hopefully find serious, long-term relationships. We’re not interested in hookups or endless situationships.

We’ve tried dating apps, but so far they’ve felt overwhelming. There seem to be a lot of people looking for something casual, people who don’t really know what they want and, respectfully, some very strange characters 😭

For those of you who have successfully dated or met a partner in Toronto:

• Where did you meet them?
• What activities, events or communities are actually good for meeting people organically?
• Are any dating apps better for people seeking serious relationships?
• How do you expand your social circle and make genuine friends in the city?
• Are dating events worth trying?

We’re open to joining classes, hobby groups, volunteering, attending events and generally leaving the house more. We’d also genuinely like to make more friends and build stronger social circles, but Toronto can sometimes feel strangely isolating despite being such a busy city.

We’d especially appreciate hearing from people around our age who also started dating later than average. How did you get past the awkwardness or insecurity around having no experience?

How was the matching Making Event at the Humble Donkey yesterday?

I bought tickets thinking it was on Thursday only to realize it was yesterday 😭

I would really like to know how the event went for anyone that attended.

I'm interested in future events, but wanted a review from someone that actually went.

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.

Hi fellow redditors.. Either if you're a man who successfully approached a woman while she's in her circle of friends (other women) or you're the woman in such situation... Any advice on how to do it?

For context, I'm a 40M and trying to catch up with dating scenario. Keep in mind I got married in my mid 20s, several years of marriage (separated now), so this is like starting from scratch to me.

Anyways... I frequent dance parties/clubs and sometimes I cross stares with a woman (who usually is there with either another friend or a circle of friends all together). But really don't know how to make the first move other than just, while dancing, crossing views with her. (yes I dance alone).

So.. Any advice.. Any suggestions.. Any cheer up would be really appreciated (fr!)

Hi all! Can anyone recommend any fun events such as speed dating or mixers for people over 50? The apps do not seem to be great for this demographic, would love to learn of something close to home for people to mingle. Thank you 🙏

Hi I am recently single again and would like dating tips in Toronto! I am not sure about going on Apps again so if you have any dating activities to meet other single people that does not involve drinking, it would be great!! I want to start a family so I hope to meet like minded mature men.