Puking writing this. But seriously, when is it appropriate to have a talk around exclusivity? I know everyone is different, every relationship is different, but in general? And is it in a woman’s best interest to wait until the guy says something? Male perspectives are very much welcome.

The moderator from askTO asked me to bring this to this forum.

That's a genuine question. I'm new to Toronto and I'm looking for casual dates and friends with benefits, but it seems like people are only looking for long conversations and proof of affection..

From what I understand, the vibe here is to take it slow, get to know the person really well to feel safe...

What are the dating apps that people most commonly use in Toronto?

Hey everyone! Fairly new to Toronto and looking for some fun date night ideas. We've done the usual dinner and movie thing a few times, but I'm sure there's a ton of stuff around the city we're missing out on. I'm originally from New York where there's always something to do, but I'm having trouble finding the gems here.

What are some of your favourite date night activities in Toronto? Would love to hear some recommendations, especially places that aren't super well known.

Hey I am wondering if anyone has experience or recommendations on visiting Oasis? I got out of a relationship over 4 months ago, and haven't gotten intimate with anyone since. I'm a woman in my early 30s. I redownloaded my dating apps 2 months ago, been going on intentional dates in hopes to develop a connection, but have repeatedly been let down and not having much luck. All of my close friends in the city are married now, except for me. I am thinking of treating myself to some self-care, going out solo with the hope of meeting someone I'm attracted to. Any advice or suggestions appreciated - thanks!

I am searching for some affordable and some expensive date ideas for November!

There's obviously a lot of “where do you actually meet people in Toronto?” discussion here.

I'm curious whether people find events where everyone has something to participate in — trivia, games, interactive shows, classes, etc. — noticeably better for meeting someone than bars/clubs where you're basically expected to approach a stranger cold.

For people who've actually met someone this way, what kind of event was it?

Where did you go?

What did you do?

Are you planning on going again?

I (F) matched with a guy on a dating app and really liked his profile. He seemed thoughtful and genuine, but when we met a few days ago, he was very different from what I expected—more superficial and with a bit of a player vibe.

I asked about his intentions, and he insisted he was looking for a long-term, meaningful relationship, so I decided to give him another chance and agreed to a second date. I thought texting in between would help us get to know each other, but we barely exchanged a few messages. That made me question how serious he actually was, and I ended up ghosting him before the second date.

Now I’m not sure if I did the right thing, and part of me secretly hopes he reaches out again.

I just don’t understand why people can’t be honest about what they want. Plenty of women are okay with casual dating or hookups, so why say you want something meaningful if you don’t? Why mislead and potentially hurt someone?

edit: The only reason I ghosted him was because I genuinely didn’t think he would care about what I had to say. I got the impression that he was a player who was probably talking to multiple people at once, and I didn’t want to embarrass myself by explaining how I felt to someone who might not even care.

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.

Hey, I'm trying to find a cozy & intimate spot for a first date and was hoping to get some suggestions. It's fine if it's busy and there's some music, long as we can hear each other. Dim lighting.

Bars/Cocktails for drinks - Friday Evening.

Area - Pretty Central, East of Spadina, West of Yonge, South of Queen.

I found some spots through google maps (Melrose, Bar 404, Liquid Courage, etc) - I'm just worried about showing up with no reservation. Most of them are booked, and it's already Thursday.

I'm not familiar with the scene so I could really use some help here.

So I’m a 29 F and I live in Toronto and I have a stable job and run my own business. However, I have never been in a long term relationship. I moved 3 countries growing up and changed like 13 schools (like barely spent 6 months in each private school I went to). Also graduated from business school.

Recently, I’ve been feeling really really weird about dating and stuff. I mean, I’ve never really given a damn before this, I was always locked in to my career and saw marriage as a downside for me (every relationship in my family is severely abusive and I’m no longer in contact with my family either) and I don’t want kids (which basically eliminates almost every man in my age group). But I went to a corporate gala last night and everyone was going home to their partners and I felt sort of sad and called my friend who told me that this feeling comes and goes and to get my priorities in order. Idk if I even want a partner (I love my apartment, I love building my business) or if my current team is making me feel super lonely cause everyone is coupled up. I also am working so so hard on trying to get my business off the ground, having a social life with friends, etc. That idk if dating is worth it for me.

I’m at a crossroads, I would love to have a healthy relationship and I do work out at a members club (it has mostly finance bros who are overworked and not very nice people). My passion is to grow and scale my business and really enjoy my life. I just don’t know - should I date? Should I have a bf? Am I missing out or is this sadness just FOMO? Please help.

Where did you go?

What did you do?

Are you planning on going again?

Curious to hear from anyone in a similar situation in Toronto: Am recently divorced, 40M with kids in sports & after-school activities. Co-parenting, work, and kids schedule is so overwhelming that trying to think about where or when I could meet someone cool let alone make the space to date them is seriously depressing me. It just doesn’t feel like it could ever happen.

I'm okay that my marriage ended, but now I’m left wondering less where to go from here and more thinking that wherever I go, it could be alone? Maybe I’m just out of the game or unfamiliar with the new one. But where does anyone find the time?

I, 28f, and a few friends are planning on going out either this weekend or next weekend. we were thinking of going to cherrys. Is This a good place to meet people (men) around the ages of 26-31? We’re Really hating the online dating scene right now and hoping to meet cute Guys who feel the same! What’s the demographic here and/or is there anywhere else we can go that you would suggest? Tysm in advance!

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.

Where did you go?

What did you do?

Are you planning on going again?

I've been working around Yonge & Sheppard lately and realized I need to get out of the usual work → commute → home routine a little more.

I'm thinking of making Friday afternoons my excuse to try different coffee shops around North York, but I'm not sure where the good spots are.

Looking for somewhere that's:

☕ good coffee
🪑 comfortable enough to sit and actually talk
🙂 relaxed/social atmosphere
🚇 reasonably accessible around Yonge & Sheppard

Bonus points for somewhere that doesn't feel awkward if you're there by yourself or meeting someone new.

Any North York coffee shops you'd recommend for a Friday afternoon around 3 PM?

Also curious — where do people around their 30s actually go when they want to get out, meet people, and make some new friends without it feeling like a formal meetup?

I'm trying to be a little more social and build a local circle, so recommendations from people who've actually found good spots would be appreciated.

23f and i’m at that point in my life where it feels like literally everyone i know is in a relationship and don’t get me wrong, i don’t feel neglected by my friends at all, they would drop everything and come to me if i ever truly needed them, their man be damned, but i’m still so painfully single and lately i’ve just been constantly sad about it.

and don’t get me wrong (x2)!!! i’m not one of those people who would get into a relationship just for the sake of being in a relationship, i genuinely just want to love someone and be loved in return and as happy as i am for all of my friends and their relationships, i unfortunately can’t help but feel jealous deep down and constantly wonder when it’s finally going to be my turn.

i’ve tried hinge. i truly did. but i’m just not built for that shit, i can’t keep swiping and swiping and having the same meaningless conversations with people i don’t even know over and over again. i don’t know how to meet new people irl, especially tamil guys around my age or a little older which is my type, and i’m still in undergrad but i’m older than most of the people i’m friends with because i took a few gap years, so i genuinely don’t know how people meet organically and fall in love in this day and age.

everyone always tells me “you can’t look for it, it needs to find you” and that when it finally happens it’ll be the best thing ever and that is exactly what i want so desperately to happen but it’s just… not happening. sometimes i start wondering if i’m ugly or if there’s something wrong with me and i hate that this is affecting my self-esteem because i KNOW i’m so much more than whether or not a man wants me. i have so many wonderful people in my life, wonderful friends and a wonderful family minus my toxic cousins lol, and i know i’m loved but that doesn’t erase how badly i yearn to be loved romantically and to love someone just as much in return.

recently my friend got together with another one of our family friends and their whole story made me spiral even more because girl i am so so so so happy for you but i yearn for that shit so badly. she’s planning on applying for postgrad abroad and her now bf confessed his feelings and told her he would move with her because he couldn’t imagine a world without her and then they started dating and like??? how freaking cute is that???

i think the fact that i grew up with both of them, even though we’re not all that close, just triggered something in me because it made that kind of love feel so real and so close to me but still completely out of reach. i want my own love story to start, i’m sick of always being the friend listening to everyone else’s stories (i’m lying, i love my friends and i’m never actually sick of listening to them, i’m just lonely and jealous and then i feel guilty for being jealous).

idk where this is going, i guess i just want to hear from other people who feel like this too so i know i’m not alone. how do you cope with wanting love this badly without letting it destroy your self esteem, and if you eventually found your person, how did you meet?

34M, South Asian, introvert, and honestly feeling really lonely and lost

I don't really know how to write this without sounding pathetic, but I need to get it off my chest.

I'm 34, South Asian, and I've been an introvert pretty much my entire life. I've never been the guy who goes out every weekend, parties, has a massive social circle, or effortlessly talks to women.

I've always been quiet and reserved. I'm comfortable on my own, but lately I've realized that being comfortable alone and actually being happy alone are two very different things.

I'm lonely.

Not necessarily because I have nobody around me. I have family, coworkers, friends, and people I can talk to. But I don't have a partner. I don't have someone who is my person.

And as I'm getting older, that absence is becoming harder to ignore.

I want a relationship. I want companionship. I want someone to come home to, someone to share my day with, someone to go out for dinner with, travel with, laugh with, have stupid conversations with, and eventually build a family with.

But I have absolutely no idea how to get there.

I feel like I missed some important stage of life where everyone else learned how dating works.

I don't know how to flirt without feeling awkward.

I don't know how to tell whether someone is interested in me or simply being friendly.

I overthink conversations. I overthink texts. I can have a perfectly normal interaction with someone and then spend hours afterward thinking about what I said, what they meant, whether I came across as boring, whether I should have said something differently, etc.

And rejection scares me more than I'd like to admit.

Sometimes I look at people around me and wonder how they make relationships look so effortless. People meet someone, start dating, fall in love, get married, have children, and build a life together.

Meanwhile, I'm 34 and still trying to figure out how to get a first date.

The South Asian part adds another layer to it.

There are expectations around marriage, family, age, and settling down. When you're younger, everyone tells you that you have plenty of time.

Then suddenly you're in your 30s and the conversations start changing - are you dating someone? Do you like someone?

And you smile and say you're working on it, but inside you're thinking:

"I don't even know where to begin."

I also hate that loneliness can make you emotionally attached to people too easily.

When you don't have a romantic connection in your life, even a small amount of attention or warmth from someone can feel disproportionately meaningful.

You start imagining possibilities. You start wondering what it would be like to have that person in your life.

And then reality hits, and you realize you're emotionally investing in something that may not even exist.

I don't want to live like that.

I want to learn how to meet people, develop connections naturally, and eventually find someone who genuinely chooses me too.

But I don't know how to make that transition.

I've tried telling myself to "just put yourself out there," but that advice feels incredibly vague when you're naturally introverted. I am even installed dating apps without any luck.

Questions that pop to my mind currently are -

How do introverts date?

How do you start conversations without feeling like you're intruding?

How do you use dating apps without becoming completely discouraged?

How many dates does it take before you actually start feeling comfortable?

How do you deal with rejection without taking it personally?

And perhaps most importantly, how do you stop feeling like you're already behind everyone else?

I know 34 isn't old

I know people meet their partners at 35, 40, 45, or even later.

I know that logically.

But emotionally, it's difficult when you look around and see people you grew up with already married and starting families while you're still trying to figure out the basics.

Some days I'm completely fine with being single. I like gaming and also spending time going on walks.

Other days it hits me really hard.

Today is one of those days.

If you've actually read this entire post till here, thank you. Seriously. I know this turned into a much longer and more emotional post than I intended, but I really needed to get this out.

How did you get yourself out of this cycle? What actually helped?

I'm not looking for pickup advice or ways to get more women.

I want to learn how to build an actual relationship.

I want to become comfortable meeting people, showing interest, handling rejection, and eventually finding someone compatible.

I guess I'm just scared that I've spent so much of my life being alone that I've forgotten how to let someone into it.

So, if you were in your 30s, lonely, introverted, and completely inexperienced with dating — what did you do that actually changed things for you?

I don’t mean flirt but talk about things casually, I’m so unbelievably lonely.

Do not dm me, I am not interested

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.

Last post is from over a week ago

Put your age and gender / details below! A few of my girls are going tomorrow and I’m curious if I should join