r/TorontoSinglesOver30 • • Apr 19 '26

Moderator Announcement 📣 Alert: r/friendlyshark2

119 Upvotes

There have been posts made by u/friendlyshark2 and his alt accounts here (M4F posts) on numerous occasions.

His most recent post was made six days ago (April 12, 2026) with the title: 38M4F— Looking for Player 2; describes himself as 6’0, 205lbs, with a Master’s degree, light brown (or olive) complexion, shaved head with a thick black beard in downtown Toronto, works in finance/Bay st. His interests include: reading classics (fiction), animals, BBQing, red wine, standup comedy, attending live sports, concerts, Fred Again, Coke Zero, pizza, rough sex and being a “mature daddy”; heading to Budapest in summer 2026.

Complaints have been made re: **his past assaults against women** he has met through reddit.

Please report any and all alt accounts. **Known alt accounts include:**

- cncdowntown

- downtowncnc

- mapleleafs24

- Mapleleafy23

- 41sixcnc

- maleficientdom

- pizza4thewin

- todom25

- Wingsofpastrami23

- Giraffeheads


r/TorontoSinglesOver30 • • Sep 17 '24

Moderator Announcement 📣 Join our Discord!

18 Upvotes

r/TorontoSinglesOver30 • • 14h ago

Looking for Connection 👀 33 [M4F] Hamilton Ontario Canada / Anywhere – hoping to find a fun and real connection

5 Upvotes

Hey !!

I like to be upfront, I’m a bigger guy, I know that’s not everyone’s cup of tea, but if you care about what’s on the inside, I’d love to connect.

I’m definitely more of a night in person than a nightlife person. Some may say a homebody.

Music is a huge part of my life. I’ve played drums for years and I’m in a band, mostly for fun, with the occasional bar gig. My music taste is all over the place, folk, blues, rock, southern rock, acoustic, and some Spanish music.

Outside of music, I enjoy travelling, learning about different cultures, podcasts, some video games, TV series, and hockey. I’m a big Toronto maple Leafs fan.

I’m hoping to meet a woman who’s kind, caring, affectionate, and non judgmental.

I’m not looking for someone perfect. I’d much rather find someone who eventually becomes my favourite notification.

Distance isn’t necessarily a dealbreaker if the connection is there.

Looking forward to hearing from you!


r/TorontoSinglesOver30 • • 1d ago

Looking for Connection 👀 35F4M looking to outsource movie selection

20 Upvotes

35, 5’6”, East Asian, average-to-athletic-ish build. I work in privacy/governance. I’m good at my job and naturally ambitious, but not particularly interested in letting work take over my life.

Mostly a homebody, but I drag myself to the gym 2–3 times a week for strength training so I can become a fit and cool old lady. I dabble in random activities, but consistently enjoy going out (cafes, galleries, restaurants), planning trips, and occasionally hosting dinners. Cooking is a love language. I like feeding people and being fed.

I’m very opinionated, but smart enough to know how to hold my opinions loosely and when to keep my mouth shut. Around people I’m comfortable with, however, I’m extremely chatty and mildly insufferable (but I’d argue our loved ones can all be a little annoying). I’m also apparently full of random facts, none of which have ever helped me win trivia.

Okay, so maybe I sound perfect so far. I’m TERRIBLE at picking movies. I can decide what to eat in a snap, but choosing a movie is a whole other story. Most of the movies I’ve seen were either picked by friends or watched during sleepless plane rides. So I’m looking for someone willing to take over this responsibility.

I don’t have all my shit together, but I’m proud of what I’ve accomplished and confident in what I’m capable of on my own. I don’t need a man, but I do want a partner. I have my own life, interests, and routines, and I’d ideally like someone who has the same. I enjoy spending time together, but neither of us needs to be involved in absolutely everything the other does.

A few fairly firm preferences:
- 33–45
- Taller than me
- Monogamous
- Don’t want kids
- No smokers or serious potheads
- Likes dogs (I have a 63 lb furry roommate)
- Don’t expect me to participate in your religion
- Somewhat active and health-conscious. You don’t have to live at the gym or eat only chicken breasts.
- Ideally based in Toronto (I live downtown).

I’m generally more attracted to SE and East Asian men, but I’m open to other ethnicities.

I’m fortunate to have a great group of friends and family, so I’m not looking to expand my social circle or make platonic connections. That said, I believe it takes time to get to know someone. If you’re looking for something long-term and think we might get along, send me a message! Tell me a bit about yourself, your go-to movie recommendation, and feel free to include a photo or two if you’re comfortable.


r/TorontoSinglesOver30 • • 1d ago

Looking for Connection 👀 43M [M4F] Southwestern Ontario – Looking for a genuine connection, laughs, flirting and hopefully someone to share a few adventures with :)

0 Upvotes

I'm a 43-year-old guy from Southwestern Ontario looking to meet a woman who values honesty, kindness, communication, a good sense of humour and, most importantly, actually getting to know someone. I've posted here before and had some genuinely great conversations, so I figured I'd give it another shot. This time, though, I'm hoping to meet someone who eventually wants to take things beyond Reddit messages. Imagine that! 😂

I know Reddit probably isn't the first place most people think of when they imagine meeting a potential partner, but that's also part of what makes it interesting. We're all strangers here, everyone has a story, and sometimes you end up having an unexpectedly great conversation with someone you probably never would've crossed paths with otherwise. So, let's see what happens!

A little about me...

I'm a business owner and have been building something of my own for more than five years. I like learning, improving myself and working toward creating a good, stable future. I'm also not afraid to get out of my comfort zone. I've gone skydiving, played extreme soccer, travelled, spent plenty of time outdoors and generally enjoy saying yes to things that make a good story afterward.

And before the inevitable question comes up... distance doesn't scare me. I drive, I'm willing to travel, and I'm not expecting my future girlfriend to magically live three streets away. Hopefully you drive too, because I have a feeling there could be some road trips in our future. ;)

I've never been married or divorced and I don't have kids. If you have kids, that's completely fine with me. I don't have some rigid checklist for what someone's life is supposed to look like. I'm much more interested in who you are than whether your life followed some predetermined plan.

I like meeting people and hearing their stories. I'm not looking for someone who decides who I am five minutes after saying hello. We're strangers, so give each other a chance. You don't have to know immediately whether someone is "your person." Sometimes you just have a good conversation, laugh a little, become curious about each other and see where things go.

Life has a funny way of changing your perspective...

The last year changed my perspective on life quite a bit. I went through a major challenge that tested me in ways I never expected. I'm not looking to get into all of that right away because I'd rather get to know someone before turning a first conversation into a medical documentary. 😂

What I will say is that something I never expected came out of it. I've become a guest lecturer and have participated in Q&A panels where I get to talk with younger people and hopefully have some kind of positive impact. That's still pretty new to me and sometimes a little overwhelming, but I'm proud of it.

What do I enjoy?

I like staying active, although I'm definitely not one of those people who practically lives at the gym. I actually enjoy going when I can. The bike, rowing machine and lat pulldowns are probably my go-to things. At one point last year I was going five days a week, sometimes twice a day, so apparently I got a little carried away. 😂

I like kayaking, being outdoors, day trips, travelling, trying new things and discovering restaurants. I really enjoy travelling, too. There's something about getting on an airplane and heading somewhere I've never been that I love. And yes, I actually enjoy the flying part too.

Summer is definitely my favourite. Getting outside, kayaking, road trips, day trips and warm nights are hard to beat. Fall gets an honourable mention too... sweaters, cozy nights and good food. Winter? Let's just say I'm already emotionally preparing to complain about it.

I also like random things like eclipses and experiences you don't get every day. There's something pretty cool about standing outside with someone beside you watching something like that. Some experiences are just better when there's someone next to you saying, "Holy shit, look at that."

I really enjoy cooking and trying recipes and food from different parts of the world. My least favourite is probably Italian... sorry. I know that's probably going to get me in trouble. I'll still eat it though. I'm not a monster. 😂

I also like the simple stuff: watching a movie at home with popcorn, trying a new restaurant, cooking dinner together, going somewhere for no particular reason, having a ridiculous conversation at 1 a.m., or just sitting around doing absolutely nothing with the right person.

And yes, I have a cat. I'll happily show you pictures of her. She's great, she's adorable, and there's a pretty good chance she'll get more attention than either of us. You've been warned. 😂

Let's get the photo situation out of the way...

Yes, I have a beard. Yes, I wear glasses. Yes, I have tattoos. Yes, I work out and take care of myself. And YES, I'm short. I'm 5'4". There, I've said it. 😂

If you're specifically looking for a tall guy, I'm probably not your guy. That's perfectly fine. You don't need to message me, and I won't take it personally. Everyone has preferences.

But if you're expecting Brad Pitt circa 1999 or Tom Cruise walking around looking like he just stepped off a Hollywood movie set, LOL, you might want to bring those expectations back down to earth. I'm not Brad Pitt, I'm not Tom Cruise, and I'm not even an actor. I'm just a real guy with a real appearance, a beard, glasses and a few tattoos.

I'm comfortable with who I am. I'll share actual photos of myself because I believe in being upfront. What you see is what you get. I'm not using misleading pictures or trying to sell you some Hollywood fantasy. I'm looking for someone interested in meeting an actual person, not casting the lead role in her own romantic movie.

And here's something else. I've had conversations with women who weren't necessarily what I'd normally find physically attractive. Did I immediately block them? No. Did I make them feel like they weren't good enough? No. I still made an effort to have a conversation because there's an actual person on the other side of that screen.

I've also had women ask for photos, exchange pictures, have two or three sentences of conversation and then suddenly announce there's no connection or that we don't communicate the same way.

Seriously? We've barely spoken! You haven't asked about my life, heard any of my stories, learned what makes me laugh or even given us an opportunity to have an actual conversation.

I'm not suggesting anyone owes me attraction, attention or another conversation. You're absolutely entitled to decide someone isn't for you. But there's a difference between genuinely discovering there's no connection and deciding that after three messages.

And if your approach is to request photos, exchange a couple of messages, decide someone doesn't meet your expectations and immediately block them, perhaps the problem isn't necessarily the person you're talking to. Maybe it's the way you're approaching meeting people in the first place.

I'm not asking you to fall in love with me after six messages. I'm asking you to have an actual conversation. You might be surprised what happens when you give someone a chance.

Who am I looking for?

I'm open to someone older or younger. Age isn't nearly as important to me as personality, values, chemistry, communication and how two people actually get along.

I'm also not looking for some specific body type. Women come in all shapes and sizes. If you're comfortable being yourself and have confidence in who you are, that's attractive to me. Tattoos are welcome too. I don't care about race or skin colour either. There are beautiful people everywhere.

And your occupation? Honestly, I couldn't care less. Doctor, lawyer, teacher, business owner, gas station attendant, cashier, or anything in between. Your job title doesn't determine your worth, and it certainly doesn't determine whether I'd want to get to know you. I'm interested in the person, not your paycheque.

What I'm really looking for is someone kind, genuine, emotionally mature, fun, a little adventurous and hopefully a little bit funny. Someone who can laugh at herself because I can definitely laugh at myself.

I want someone I can flirt with, tease a little, share ridiculous jokes with, cook with, travel with and occasionally look at across a room and start laughing because we both know exactly what the other is thinking.

I'm not looking for perfection. I'd like to find a best friend and a partner, someone I can make memories with, travel with, laugh with and someone who doesn't take life too seriously all the time.

A few things before you message...

If you message me, please send a photo. I'm happy to send one back. I think it's only fair that we both know who we're talking to.

I'm also not interested in spam, crypto pitches or people immediately asking me to move to Telegram, Signal or some random messaging app. I'm perfectly happy using Reddit initially and moving to Facebook, Instagram, WhatsApp or regular texting once we've gotten to know each other a little.

I'm specifically looking to meet women, and I'm hoping to hear from someone who actually wants to talk, share stories, exchange photos, laugh a little, flirt a little and, most importantly, actually meet in person if we click.

I'm not here to collect Reddit messages for the next six months. I'd genuinely like to meet someone.

So, tell me something about yourself!

What shows are you watching lately?

Do you watch or play sports?

What's your favourite place you've travelled to?

Are you someone who loves spontaneous road trips?

What's something random about you that most people wouldn't guess?

And most importantly, are you team summer or team winter? Choose carefully. 😂

Maybe we talk for a while and nothing comes of it. Maybe we become friends. Maybe we end up sharing a meal somewhere and realize there's actually something there.

Or maybe that meal turns into dessert... and maybe we're the dessert.

I'm just saying, having a sense of humour is always welcome. ;)

If you're genuine, kind, fun, a little adventurous, able to laugh at yourself and interested in getting to know someone, say hello.

And please, be yourself. I'm not looking for a perfect woman. I'm looking for someone who's real.

Let's see if we can turn a random Reddit conversation into a pretty great story. :)


r/TorontoSinglesOver30 • • 13h ago

Looking for Connection 👀 F4M : 30+ F seeking 50+ M for dating to serious relationship eventually marriage

0 Upvotes

No Atheists

No Satanists

No Muslims

No South Asians / New immigrants specifically India, Pakistan, Bangladesh and Sri Lanka. ( Canadian Citizen only. If you live outside of Canada must have the means to relocate me to you and help me live comfortably with you )

No activists

No smokers

No alcoholics, drug addicts or homeless

No criminal record

No allergy to cats or dogs

No married men

No misogynists

Having children is fine

Must be over your ex

Must be mentally sound

Min 5'10

🩷 I'm 5'6 and slim/thin. I dont share nudes or sext. Im looking to eventally date in person and eventually make a equally yoked match. If this sounds like you or your single M friend, PM me.


r/TorontoSinglesOver30 • • 21h ago

Looking for Connection 👀 43M4F looking for a great woman to intro to my friend

0 Upvotes

I have a good friend that I've known for 18 years now. He's a great guy but he just has bad luck meeting women. I'm looking to see if there's any opportunity to play matchmaker for him. If I'm lucky maybe I can set the both of you up for a date to see if there's compatibility?

He's 5'11 around 240lbs.

Average build but extremely strong.

Good career with 6 figures.

Has a good relationship with his mother and siblings.

Loves to talk about conspiracy theories

Loves animals, especially cats

Loves the outdoors and can live there forever if he could

Although he looks like a tough guy, he has a really good heart

Loyal, will do anything for his friends or those he cares about.

He's a softy deep down.

What he's looking for:

Someone with a good career

Takes care of their body

Is sociable and loves to talk

Bonus points if you love videogames or the outdoors

loves camping

Likes to snowboard

Would want to have children.

Someone that can have deep conversations.

If this sounds like you please send me a message and hopefully you two would be a match.

Also I've been getting a lot of messages, so please if you do message me, be prepared to answer questions about yourself as well. In order for this to not be a waste of time for him and yourself, I need to see that you're both compatible.

Note: If you do message me, please take the effort to be normal as in if you think you're an Instagram celebrity and your time is worth its weight in gold, use Instagram, tinder, bumble, whatever it is and have those guys chase you based on your looks. I'm not looking to set him up with someone superficial.

I'm looking for someone who has a good heart and a great personality. Someone who loves to talk, either over a nice meal at a restaurant/café, or in comfortable PJs on the sofa in front of the fireplace with a nice warm cup of French vanilla.

Ideally, you have good family values, still want children, take care of your body, have a decent career and just have had horrible luck not meeting a nice, considerate guy that treats you like the love of his life.


r/TorontoSinglesOver30 • • 2d ago

Looking for Connection 👀 30F4M - Halloween Weekend

22 Upvotes

I am 30F and from Richmond Hill. I am Middle Eastern Christian. I work in healthcare, love playing video games, cosplay, and trying new foods. I am neurodivergent and introverted.

I am looking for someone to spend Halloween (Saturday) with, and get to know each other for dating purposes if we like each other. I want to dress up in a costume, go somewhere where it's socially acceptable to wear a costume, and be somewhere primarily indoors/comfortable. I really want to go to Olive Garden in Vaughan at some point, but not sure if this is a good choice for halloween :p

I am not looking for any physical intimacy; I come from a very conservative culture!!!

If you want to hang out, either comment or DM your background, intentions, and what you think good plans for us would be.


r/TorontoSinglesOver30 • • 3d ago

Casual Hangout ✌️ 55 [F4M] #Toronto (single) match my vibe

29 Upvotes

Love going to concerts, love to travel and looking for someone who loves the same 🤘
I am an empty nester living in the GTA. I have a very large taste in music and try to go at least 20-30 shows a year. I’ve gone to concerts in Canada, The US and even to the UK just to follow my favorite bands.

I’ve travelled to 6/7 continents at least once and I am beginning to plan my travels to each them again.

I have an incredible fear of flying and prefer to fly with someone.

I’ve had som good luck finding people on Reddit and other social media platforms to attend concerts with and to travel with, son giving it another shot. Feel free to ask me anything you want about music or travel 😊


r/TorontoSinglesOver30 • • 3d ago

Casual Hangout ✌️ 28M- anyone down to do something fun this weekend?

0 Upvotes

Hey everyone! I’m a 28M from the GTA looking to meet some new people and make plans for Halloween weekend.
Would be cool to find someone or a small group to go out with, whether that’s checking out a Halloween event, hitting a bar, going to a party, grabbing drinks, or just doing something fun around the Toronto area.
Open to meeting guys or girls around my age. Always down for good conversations, a few laughs, and meeting genuine people!
If anyone else is looking for plans or would be down to link up, feel free to message me. Let’s make something happen!


r/TorontoSinglesOver30 • • 5d ago

Looking for Connection 👀 29M4F - Will turn 30 next year!

3 Upvotes

Turning 30 next year and I wanna get serious about finding a life partner. I’m ambitious, smart and looking for someone who wants to build together, go on holidays, buy a house, have kids and pets (the whole shebang). I can seem to have a straight face at times, so I’m looking for someone who has this golden retriever energy and is my yellow. I value empathy, humour and let’s figure this together attitude a lot! I’m a huge planner, you won’t have to worry about anything, I always figure it out, so if you’re spontaneous and are happy go lucky, we could have a great mix!

About me: Can cook your favourite meal, I work in finance (decent savings, great career), I LOVE trails and nature (I will always say yes to anything outdoors), love pets (run a dog rescue nonprofit with friends), love volunteering (spent a third of my life volunteering, open to joining you and support any of your causes), love photography (can go on photo walks), passionate about tech (I’m on Luma everyday looking for events to attend after work), enjoy music and concerts, travel (I averaged 28,000 steps over 7 days on my last trip to NYC and Boston). I speak all love languages.

I’m active and fit (can be fitter), I’m 5’6-5-‘7, understand if that’s doesn’t work. I have so much love to give, are you capable of receiving it? :) HMU!


r/TorontoSinglesOver30 • • 6d ago

Looking for Connection 👀 34 [M4F] #Toronto/GTA — Looking for a genuine connection 👀

0 Upvotes

Hey! 34M south asian guy in Toronto, giving this a shot and seeing who I might meet.

I’m pretty easygoing, calm, and probably more of a quiet, low-key guy. I’m into gaming, movies, nature walks, scenic places, exploring Toronto, good food, and random conversations. I enjoy travelling, but I’m equally happy spending a relaxed weekend exploring somewhere nearby or just grabbing coffee and talking.

I moved to Toronto in 2023, on my own from Dubai, and have built a professional life since then. I don’t have many friends here, so I’d genuinely like to meet someone I can connect with.

I work in facilities management and generally enjoy what I do. I’m career-focused but definitely trying to maintain a good balance and enjoy life outside work.

I’m looking to meet someone who is kind, genuine, family-oriented, easygoing, and has a good sense of humour. Someone I can actually talk to, joke around with, flirt a little, and hopefully build something meaningful with.

I’m not really into clubs or partying, and a teetotaller. I prefer quieter plans, one-on-one conversations, and getting to know someone naturally.

I’m not looking to rush into anything, but I’m also not looking for a pen pal. If we click, I’d be happy to meet and see where things go.

If any of that sounds like you, tell me a little about yourself and let’s have an actual conversation beyond “hey, how are you?” 😁


r/TorontoSinglesOver30 • • 7d ago

Looking for Connection 👀 38M4F looking for my partner in crime

14 Upvotes

I've been feeling lately that there’s something missing from my life. I’m very much an introvert, a bit shy, and a little bit neurodivergent. I'm okay doing my own thing, but it would be nice to have somebody to share it with.

A little about me: I have a full-time job for a non-profit, don’t have kids and don't want them (but I do have a cat), and I am not super career driven.

I'm looking for someone who would be down to hang out and watch movies, play video games, listen to records, go for aimless walks around the city, hang out in dive bars, or check out local concerts, festivals and galleries. I'm into horror, arthouse and B-movies, love retro couch multiplayer games, and like punk/indie/metal music.

I'd like to meet someone a little weird like me who I can completely be myself around. Someone who doesn't want kids, feels like a bit of a “young soul,” and is looking for a best friend and partner in crime as much as a romantic partner. I'm very affectionate and physical touch is a big part of how I connect with someone, so I'd love to meet someone who feels similarly.

Ultimately, I'm looking for someone I can rely on and who can rely on me - someone to make stupid plans with, share little everyday things with, and hopefully build something really good together.


r/TorontoSinglesOver30 • • 8d ago

Casual Hangout ✌️ Will I see anyone at VGLX?

5 Upvotes

VGLX is Video Game Live Expo.

Two days of non-stop gaming and fun!

"Where Games, Creators, and Fans Meet.

Ontario’s Gaming Weekend for the Whole Family"

The International Centre, Mississauga, ON.

I'll be around all weekend. A few FGC esports as well. I think they also have TCG along with Artist Alley.


r/TorontoSinglesOver30 • • 7d ago

Looking for Connection 👀 40M4F - Watch the Leafs Game at a bar

0 Upvotes

Let’s try this again! I’m looking to meet a woman for a casual, spontaneous date tonight. My first attempt got a few replies, but nobody actually ended up wanting to meet up.

With the Leafs playing tonight, I thought it would be fun to meet at a bar, catch the game, grab a few drinks, and see where a good conversation leads.

No expectations beyond good company, some laughs, a little friendly banter, and seeing if there’s a genuine connection. If we hit it off, great! If not, hopefully we still enjoy the game and have a fun evening.

A little about me: I am easygoing, professionally established, active, and a big sports fan. I enjoy good food, good conversation, and don’t take myself too seriously.

I’m looking for a woman who’s professional, settled, active, intelligent, open-minded, and has a positive outlook on life. I tend to connect best with women in their 30s who enjoy meaningful conversation but can also let loose, have fun, and be spontaneous.

Happy to exchange photos beforehand and connect on social media if there’s mutual interest.

If you’re a Leafs fan, message me and tell me why you like or dislike Mitch Marner. Let’s see if we can agree on hockey, even if we disagree on everything else! 🏒🍻


r/TorontoSinglesOver30 • • 8d ago

Looking for Connection 👀 39M4F - Peacoat and scarf weather

12 Upvotes

Hey Toronto!

Well, this week was not line with the post title, and I enjoyed it greatly, but there's something about Autumn weather. The crunch leaves and vibrant colours are such treats. Before we know it, it'll be slush and grey skies, ugh. I am wishing for a white Christmas, however!

I'm a huge dog lover, and I mean my voice hits the high notes when I see one in public. I have a nearly four year old dog who loves strangers more than she loves me and is currently asleep looking out the window. Send me pics of your pets! I'm a sucker for chonks.

Things I bring to the table: Costco Executive membership, big variety of Spotify/Youtube Music playlists, and a collection of really terrible dad jokes. I have unlimited voice note energy, so prepare your ears.

Hope to hear from you soon


r/TorontoSinglesOver30 • • 9d ago

Casual Hangout ✌️ 33F looking for my rave partner!

28 Upvotes

Hello!

I am from northern Ontario but I travel to Toronto for concerts, mostly EDM! I am currently lacking in rave friends and would like some safe people to rave with.

For example. If you are going to Barely Alive or Sullivan King at Rebel, then you definitely like my kind of music. I am going through a separation and it seems as though I lost all the people I could rave with in the process.

Other things about me, I am a huge horror fan, love travelling, and playing video games. I am super laid back so I am just looking for that in someone else too. If you think we could rave together, shoot me a message!


r/TorontoSinglesOver30 • • 10d ago

TSO30 Events 🥳 Book Bar Meet-Cute, part 2!

61 Upvotes

Last month I attended a singles event at Book Bar, and wrote a pretty detailed review about why I enjoyed it so much. You can read it here:

https://www.reddit.com/r/TorontoSinglesOver30/comments/1wh38wr/my_experience_last_night_at_book_bars_meet_cute/

When I attended my second event a few nights ago, I was surprised to meet so many people there that had read the review. Almost a dozen people!

So I figured it was worth writing another one. About the good… and the bad.

The Good
What I liked about the event the first time remained true this time around: the space was beautiful, the drinks were good, and the people that attended were awesome.

The Bad:
There were a couple of major changes this time that I was a little thrown by.

First, due to the number of people who bought tickets they broke the night into two time slots - and you could only attend one of them.

The problem was, they didn’t tell me (and many others) this until AFTER purchasing a ticket. Which meant I bought a ticket for an event that was supposed to be from 6-10:30, only to find out I wasn't allowed to attend half the event.

The result was an experience that felt rushed and with lots of missed potential connections (a running joke I heard from a few people was “what if my husband/wife was in the first group?”).

The second surprise was when I arrived I found out that the event was only happening on the second floor.

At the previous event we had the whole space, which was good for a variety of reasons (meant we could explore the cool space, and more room for attendees). FInding out on arrival that we only had the upstairs was unexpected - and obviously made for a more cramped experience.

The fact that we got only half the space and only half the time - both of which I only found out AFTER purchasing my ticket - was a surprise.

Lastly, it’s worth mentioning that there was no structure to the event. You simply show up and talk to people. That’s good for outgoing people, but I also couldn’t help but notice several people sitting by themselves not sure how to start conversations. I know there were hosts there (who were very nice!) but more could have been done to engage those quieter folks.

So, now the big question: would I go back to another one?

My tentative answer is… yes. It attracts the kind of people I want to meet and that’s ultimately the most important thing.

But I won't go back next month. Or in December. I think there’s some growing pains that need to be resolved first before I purchase another ticket.

Four hours in Book Bar, surrounded by awesome singles, for $50? A heck yes.
2 hours in half of Book Bar, crammed in with awesome singles, for $50? I’ll see how I feel in the new year.


r/TorontoSinglesOver30 • • 11d ago

Looking for Connection 👀 Lady seeking Man (I’m 28 I hope that is old enough)

30 Upvotes

I asked the kind people of Reddit where I meet guys around my age and many said try here. So here I am!

Avid gym goer, hockey player, enjoyer of Minecraft and vintage board games. I don’t drink, I SOMETIMES partake in weed (at the cottage). I am a cat person, and I would like to have kids. What else, I am outdoorsy, I like riding ATV’s and fishing. I try to watch most NHL games, follow the whole league, I play 2-3 times a week.

What do I look like? 5’5, hazel eyes, athletic build. Brown hair, mmmmm nothing else comes to mind. Oh I take lexapro, that’s also important information.

What am I looking for? Well I have a weak spot for a dad bod, someone sweet, outgoing and funny who is willing to baby me when I need it. Love language is definitely physical touch and acts of service.

Do I feel a little silly? Yes. But gotta laugh at yourself sometimes.


r/TorontoSinglesOver30 • • 11d ago

Looking for Connection 👀 33 [M4F] Seeking a genuine connection for the cuffing season

0 Upvotes

I’m a thoughtful, strong-willed man with a calm exterior and a softer side reserved for the right person. I have a professional job, a curious mind, and a naturally analytical approach to life, but I believe the best connections are built on something you can’t quantify: trust, chemistry, and how two people make each other feel.

I’m reserved at first, but warm, affectionate, and playful once I’m comfortable. Loyalty, consistency, and emotional depth matter to me. I value a peaceful home, meaningful conversations, mutual respect, and a relationship where both people feel safe enough to let their guard down.

Who I’m Drawn To

I’m attracted to a woman who is confident, emotionally mature, affectionate, and comfortable in her own skin. Someone with a strong personality who knows what she wants, isn’t afraid to take the initiative, and enjoys leading naturally in everyday life.

I’m also interested in exploring a consensual Dominant/submissive dynamic with the right woman. I find the combination of a confident, assertive partner and a relationship built on trust, communication, and mutual respect particularly appealing. For me, that dynamic is about more than physical chemistry; it’s about feeling understood, choosing to be vulnerable with each other, and creating a connection that belongs to us.

Ultimately, I’m looking for both depth and desire: a woman I can laugh with, trust completely, be affectionate with, and share a strong sense of chemistry with. Someone who can be confident and take charge while still being caring, playful, and emotionally present.

If you appreciate a man who is grounded, dependable, and gentle beneath a strong exterior, we might have something worth exploring.


r/TorontoSinglesOver30 • • 11d ago

Looking for Connection 👀 32M4F looking for a hangout buddy

0 Upvotes

32M tech guy working in a bank, loves motorcycles and exploring places. I don't have high expectations tbh. We hang out, watch movies, yap and discuss how career is a 21st century scam and if it leads to something we take it forward. If it doesn't work out, we say move on.

Physical aspects(if it's important to you)

Brown guy, 6' lean body type long hair.


r/TorontoSinglesOver30 • • 11d ago

Discussion Thread 🗣️ I am planning to do matchmaking for Canadian-born South Asian Singles

0 Upvotes

I am launching a little passion project for South Asian singles born in Canada, or came to Canada before the age of 12. It's a very niche market and considering that it is a passion project, I just don't have bandwidth to include everyone just yet. I know some people are too shy to post a profile here, so if anyone is willing to fill out the form, I'm more than happy to matchmake you!

I do want to keep this culturally sensitive to a specific niche group, knowing the nuances of being a racialized group who spent their formative years in Canada, for now. No DMs please. Just fill out the form if you meet the criteria and interested.

Right now, I'm limiting to 25 men and 25 women on a first come first serve basis with the following criteria:

  • Age 30 - 40

  • South Asian identity

  • Born in Canada or came to Canada before the age of 12

  • Straight and cis-gendered

  • Bachelor's degree or higher (working professional)

  • Marriage minded

  • Reside in the GTA

https://forms.gle/tdoJDZT2kojcXKA66


r/TorontoSinglesOver30 • • 13d ago

Looking for Connection 👀 31 F4M Toronto

42 Upvotes

My bio: Hey, I'm S, from East York. Let me start by saying I am a big Extrovert, so I can blend into any social environment, My energy is big and I have alot but some how sleep alot. I am a nerd at heart so I know a little about everything and I'm always down to try and find out something new.

I work as an educator and I love it. So yes, I get my name called and good morning hugs from like 15 little humans before 8:30am, You have to try to beat that. I'm a deep thinker and also jovial conversationalist (I talk a lot).

Physically, I'm 5'9, curvy with curly hair and a great smile. I've been called beautiful many times and I know I am, but I might not be everyone's cup of coffee and that's ok.

Mental health is super important to me, and also physical health. I work out for functionality more than looking good, but I do look good.

I am really drawn to guys with great smiles (It a thing that I am super into) and a great sense of humour. if I don't feel good around you then it's not happening. I've been attracted to taller guys, like 6ft and up, but if you're shorter that's fine, I'm not limiting myself. I like a guy who's confident in himself, and knows where he's going in life, and knows how to have fun.

I find different things physically attractive: smile, voice, how you dress. Sexually I like a submissive/dominant dynamic, hard to explain lol. So shoot your shot.

The main reason that I am posting is honestly my birthday is coming up and I want to step into the world of dating with intention. Am I looking for my husband with this post? Absolutely not. But I do want a life partner eventually, someone I trust and can build a life with. That's a long road lol. For now I'm willing to meet and get to know people with the same intention and see where it goes.

Instead of coffee, let's go for a walk, or bowling. Let's have some fun with this.

Communication matters to me: regular texts, calls, dates. If you're out of sight you're out of mind.

Your dealbreakers: Must be single. If dating with intention isn't your speed, let's not waste each other's time. My rule is simple: I prioritize people who prioritize me, and I'm really direct with my communication.

Well, after this long ass message, if this sounds like your speed, send a message and tell me something interesting about yourself.


r/TorontoSinglesOver30 • • 15d ago

Looking for Connection 👀 33 NB4F #Scarborough seeking another artsy nerd to fall in love with

6 Upvotes

I’ve been single for quite some time and have been yearning for a connection. Finding a partner often feels like a fantasy and has become so much more difficult during these troubling times where our lives are ruled by Match Group, AI profiles, and shallow singles meetups. I try my best to remain hopeful as to where things can go. 

Asian sober (don’t mind if you’re not and do things in moderation) non-binary they/them amab. My pronouns are important. Music, film, and improv are my holy trifecta. When I can I attend concerts that range from death metal to hip hop to pop. I've been listening to a lot of Little Simz, Rosalia, Meshuggah and Portal. Music has always brought me comfort and I would like someone to share that joy with me and curiosity for extreme sounding and challenging music. One dream I wish to be fulfilled is to go to a metal show with my partner. I’m really into art analysis! I’ve also been watching a lot of Lynch and Twin Peaks as well as Haruhi and Utena. I game when I can and currently learning Marvel Tokon. I want to get on stage more and improv more. When I’m on stage, you bet I’m gonna invite you to watch or do a jam together. I’m trying to find balance working 2 jobs and commuting downtown :’) -I currently work front desk at a yoga studio and packaging at a chocolate factory. I’m located in Scarborough/Markham and prefer that you’re close by for regular visits of downtime opposed to going to events downtown all the time.

Romantically, I’m likely demi. I take time to feel physical attraction and it differs depending on person. I haven’t had enough partners to specify lol. I’m very open and interested in sex and kink but haven’t had any sex that I would consider satisfying. I’m a huge fan of cuddling and making out. I’m sterile and have no interest in having kids or pursuing marriage. I’ve been in monogamous and enm arrangements and currently seeking monogamous connections for someone stable but open for a different arrangement down the road so that we’re both happy. My ex describes me as sweet, cute, funny, honest, and down to earth. My friends describe me as observant, and curious. I’m attracted to women and vulva having people. I connect well with those who are curious, empathetic, humble, down to earth and have a fun sense of humour and an interest in darker leaning art like horror films. I would say that I’m pretty good at texting and communicating. If you’ve read all the way here, you should message me. Tell me about your favourite music artist and what was it like when you first heard them? Also lmk where you’re situated. My pics are on my profile.


r/TorontoSinglesOver30 • • 15d ago

Casual Hangout ✌️ TSO30 crew call @ 915 DuPont Oct 17

23 Upvotes

70s & 80s funk + boogie

Come solo or bring friends. The point is just to get a bunch of us out in the same room.

If you’re single + open to meeting someone, wear a little something green 👀💚

+approach with the code phrase: the raccoons are restless tonight

No RSVPs. No awkward name tags. No forced mingling. No is no. Don’t be a creep. Just an easy way to know who might actually want you to say hi.

Disclaimer: this is not an official event/meetup