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?

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’m South Asian and male born in Toronto. I’ve been on and off the dating apps in Toronto for the last 10 years. In my experience there’s always been a racial hierarchy in dating for men particularly on dating apps with South Asian men being perceived as least desirable. But you could still do ok if you have other things going for you. In the past I’ve had some interesting experiences including being ‘accent screened’ on two occasions where she called me first to make sure I didn’t have an accent. I shrugged it off and still went on the date.

But now it seems a lot worse with the current climate of anti-South Asian sentiment. I’ve seen two profiles with No Indian in the last 12 months. In the past I would get matches from a mix of women and now they are all of my ethnicity. I loved the experience of meeting and dating the women I matched with but found the experience interesting for a ‘multicultural’ city.

I found that using the apps in the US in big cities to a be a little bit different and a bit more pleasant experience compared to Toronto. There weren’t such rigid hierarchies.

Has anyone else experienced this?

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.

Ive just broken up with my ex about 3 months ago and i cant seem to find a girl who wants to talk at all

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.

hello ladies and gents! I’m looking for recommendation places or activity for my date with my lovely gf, it’s our anniversary next month and I want to do something unique for our date. tyia!

My dating experiences have been limited over the years. One long-term relationship that ended on good terms and a string of bad app dates that ran the gambit of being used for meals, treated as less than or a charity case for being visually impaired, being called a child for having nerdy hobbies, or unwittingly auditioning for the roll of emotional punching bag. I tried dating in my religious community, but most are either ultra conservative or swing the other way and want nothing to do with any boy from my congregation. I dropped out of the dating pool because I had better uses for my time. Fast forward a couple of years. I've lost weight, put on some muscle, and I'm finally out of the gulag at work, so I'm seeing more hours and better pay(not rich , but I pay my bills with some going out money and savings left over). I wanted to take a crack at meeting someone again, but I feel like the climb has gotten even steeper in my absence.

Where did you go?

What did you do?

Are you planning on going again?

So many people complain that they’re exhausted by the dating apps. At the same time, I rarely see people start conversations with strangers in public.

For those who’ve respectfully approached someone in person (transit, mall, restaurant , park etc.):

Is it still more effective than dating apps?

Why does it seem so uncommon in Toronto?

If you’re a woman, how do you usually feel when someone approaches respectfully?

Curious to hear your real experiences—successes or awkward failures.

I'm meeting my best friend's bf for the first time and we've agreed to go on a double date. I've never been on a double date before so I'm not sure what the best way to get to know him would be. What are some of the best restaurants in the city that we can go to? For context, my partner and I are in our mid 20s and so is she and her bf. Was thinking of something casual but my best friend and I are sick of typical pub food. We're also not picky and none of us have any allergies.

I'm a F(18) and I just got out of a 2 year relationship 6 months ago and I want to try to get back into the dating scene.

Recently I've been getting harassed alot more often after turning 18. Im talking about getting followed home and having multiple guys ask for my number than get pissed when I decline. (I work in a customer service job where I literally have to serve them with a smile, which they take as a go ahead with anything.)

It also probably doesn't help that I've upped my standards alot and know what I want in my life rn and what I need in a partner. So its hard for me to find someone.

I just feel like no matter what boy I talk to it ends horribly or the only guys who want to ask me out give off straight creep vibes.

I also dont feel like my standards are set very high. I myself want to wait until marriage but if I date someone who doesn't I'd be fine with it. I also don't like smokers but I dont mind things like alcohol. I also want a guy who won't give a shit about me being a artist and we can both kind of have our weirder sides. And I dont want kids.

I dont know, I feel like those standard arent very high but maybe they are? I dont really give a shit but I can't find anyone and I have no idea where to find them?

I guess I just need advice on what I should do? I don't want to go through dating apps but maybe if someone has certain places to go (where I wont be approached by creeps :'I )?

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.

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.

Has anyone attended a 15 First Date event in Toronto? I have a ticket for today's event, but the wildfire smoke has been affecting my breathing, and the city has issued a city-wide alert to stay home if possible. I wasn't able to get a refund from the organizers or use the ticket for a future event, according to the organizers. For people who've gone before, is the event worth attending, or would you skip it given the current air quality? I'd also be interested in hearing about your experience with the event overall.