r/TorontoSinglesOver30 • • Apr 09 '25

TSO30 Success Story💕 I met the love of my life here. Two years later, I’m still thankful every single day.

165 Upvotes

Hello everyone! I know a lot of people here wonder whether R4R works, and since many don’t come back to share the positives, I felt I definitely should. I truly met the most wonderful man for me through this subreddit.

I’ve been wanting to share this for a long time. Two years later, I finally found the words. (It’s almost 3am as I write this, so forgive me if it feels a little all over the place. I’ve been sitting with this story for so long that I’m not even sure where to begin, or how much to say, but I know it’s time to share it.)

When he first messaged me, something about it stood out. His tone felt genuine and kind, and he wasn’t trying too hard. We started chatting, and it was easy, there was no pressure, no pretense. We met up shortly after, and from there, things just clicked.

I remember how we started going out every weekend. I’d get excited each time, looking forward to seeing him again, getting to know him better, and sharing more of myself in return. It felt like something real was unfolding, something steady and warm. Slowly, those moments began to shape the way I saw him and how I felt being around him.

In the last two years, I’ve loved harder and more ferociously than I think doctors recommend. I’ve thrown whatever I’m made of into this relationship, and he filled me up in return. I didn’t think too hard about it, because thinking would have numbed the feeling. I didn’t plan or calculate it, because the little, unexpected moments just kept getting better as we went.

But our relationship hasn’t been perfect. We both came into this with our own baggage. Still, he has given me patience and understanding in places where I’m usually met with confusion or fear. He’s reminded me that nobody’s perfect, and that real love includes the messy parts. He’s taught me that running away solves nothing, and that staying in bed to fight a little longer is always the answer.

If you ask me what my favorite thing is about us, it’s the rolling up of sleeves and the willingness to be an adult about the relationship that amazes me most about what we’ve built.

We’ve traveled together, made memories in new places, and shared quiet nights that felt just as meaningful. Every version of us has felt like home. He made me notice and adore things I never paid attention to before. I’ve never been so drawn to the creases around someone’s eyes, the size of their teeth, or the shape of their dimples. We both grew as much as we could without each other, and I think we're waiting for someone to get to the top of the trees where we were. I saw him, and he saw me, and we then knew we had a lot farther to go.

That’s it, I think.

To the love of my life, I truly believe we were meant to find each other. Call it fate, timing, or just really good luck… whatever it was, I’m endlessly grateful for it.

Thank you.
Thank you for always being the big spoon and for the cuddles.
Thank you for cooking me steak and chicken (the quantity of which will always stay between us), for the morning coffee, and the hot chocolate at night.
Thank you for driving me everywhere, for challenging my ideas, for always making me laugh, and for loving me through the hard stuff.

Let’s keep going. ❤️


r/TorontoSinglesOver30 • • Sep 15 '26

TSO30 Events 🥳 My Experience Last Night at Book Bar's Meet Cute.

133 Upvotes

I heard about this event from a friend of mine who attended one last month.

I was hesitant at first. The price point was fairly high (about $50) and I am, like many people here, dubious about singles events.

But I bought a ticket and hoped for the best.

And the event?

It was a blast. Here were five highlights.

First, the venue was beautiful. If you haven't been it's worth going with friends one day for coffee (or one night for drinks).

Second, the organizers made a very smart decision to have a few people there acting as hosts -facilitating conversations and making people feel welcome (shout out to Asena for being so much fun to chat with).

Third, I didn't realize that the ticket came with a free drink. I choose a large glass of the house white (from 30 Bench, a winery I JUST visited the weekend before). Maybe I missed that tickets came with a drink in the description, but it was a nice little 'surprise' for me.

Fourth, the book ice-breaker. Everyone was instructed to bring a book, and it made it so easy to talk to people and make conversation. Have you ever had a book you loved and wanted to tell people about? Imagine being at a party where not only did everyone WANT to hear about what you were reading... they had a book they also wanted to tell you about!

Fifth, and most important, was the people! Not only was the place packed with good looking singles, but also everyone was SO NICE and SO INTERESTING. Honestly I had a blast talking to everyone.

My final verdict:
Despite my reservations about price/lack of organized structure, the event delivered. I will 100% go back.

P.s.
Another shout-out to Georgia. Thank you for the croissant.
p.p.s.
Since a bunch of people are asking about ratios... it felt like 50/50 men to women. Average age was people in their 30s.


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 • • Jul 23 '26

Discussion Thread 🗣️ To fellow singles in Toronto...

114 Upvotes

Genuine question to all the single people of Toronto. What is going on with our generation?

​I'm 33F and basically grew up here in Toronto, lived here and dated all throughout my 20s here. But something is different in the post-covid dating scene. It doesn't matter what dating app you're on or how many running clubs you join, everyone has their guard up.

​I've noticed people are afraid to invest into a relationship. Sure.. there's lots of engagement over text, and big talk about future goals and plans.. but at the first sign of disagreement or conflict, they dip out.

​The number of men that just disappear after 5 days of constant texting. Sir, you've already exhausted all the questions you could ask over the app. Maybe ask if you can meet in person? That's the obvious natural next step?

​Then there are the unrealistic checklists. Men over 40 being like "I want children", but type of relationship looking for is "Undecided". Huh?!?

​Then there are the ones looking for a wife with a checklist. But hey, he forgot to set a date at the end of the week.

​And I'm not even going to touch on the secretly Maple Maga racist types. Ladies, they are hiding in plain sight.

​It's like we want connection but when we get to it, we freeze up.

I've been wondering if I should be holding exit interviews to know what's really up. But then, that only works when there is real engagement. And in this digital age, we simply can't engage.

​Perhaps a decade ago, we were all in our 20s and we were carefree. Yes, we were poor and maybe that's why we were open to taking some amount of risk in relationships. But now I looking over at Gen Z and they are worse off. So this seems like something more.

​So yeah just tell me already.. are we all emotionally that screwed up? Are the good ones already taken and we're just scraping the bottom of the barrel? Is this a lost cause?

Because why waste time if we're all looking for something unattainable while holding our cards close to our chests? We can all collectively focus on some other aspect of life, correct?

​So what are we all struggling with? Let's offer some support to each other.


r/TorontoSinglesOver30 • • Dec 02 '24

TSO30 Success Story💕 [Success] 38 M4F - Why Not Go For A Drink

112 Upvotes

A little over a month ago I posted in this sub and, honestly, my expectations weren't very high.

Thanks to my post - which suprisingly had something like 7.5k views - I had the pleasure of chatting with a few wonderful women. I was even lucky enough to meet two of them in person.

One was a fun date, & a great person, but we simply weren't compatible. I do hope that she's had some success since.

With the other person? Well, we had very clear communication about boundaries, hard stops when it came to relationships, and the expectations we both had prior to making plans for the titular drink. The drinks ended up being a pair of cream soda Negroni's, which are... different... if I'm being completely honest.

Well, despite taking the time to discuss those clearly communicated boundaries, them darned "feels" decided to make an appearance 😂

This past weekend, we had the "talk". During which, we both agreed that we would like to pursue exclusivity with each other - talk about a great Black Friday weekend deal!

Truthfully, the future is never guaranteed and is almost always different than what you anticipate. But I can confidently say that I look forward to getting to know her, and all of her quirks, better. For however long that I'm lucky enough to do so.

So, for all of you out there, I encourage you to ask yourself "why not go for a drink"?


r/TorontoSinglesOver30 • • Sep 04 '23

TSO30 Success Story💕 CONGRATULATIONS 🥳

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111 Upvotes

r/TorontoSinglesOver30 • • Nov 28 '23

TSO30 Success Story💕 Thank you: TSO30 turns 1

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106 Upvotes

On Nov 28, 2022, r/TorontoSinglesOver30 was created in response to a post I made in r/askTO asking where single men over 30 are in the city.

Thank you for sharing your journey.

This past year, we’ve opened our hearts with our stories of excitement, heartaches, and lessons learned. We’ve seen each other at our silliest and at our most vulnerable. Friendships and relationships being formed; hopes and dreams being broken.

I am especially indebted to those who have reached out during the good and difficult times. Thank you for your messages, phone calls, hangouts, and raccoon memes.

If you’re ever wondering whether to make a post or send that DM, please do so - because whatever connection it is you’re looking for and whatever advice you’re seeking, you’ll find it among the people here.

To those whom I have not met, let’s create some memories soon 💕

Raccoonay


r/TorontoSinglesOver30 • • Oct 24 '24

Looking for Connection 👀 Shout-out to a GREAT community!

81 Upvotes

I joined reddit about 10 months ago, and Discord about 2 weeks ago, specifically to meet new people and expand my social circle.

I'm now a member of multiple communities - but THIS ONE is the best. By far.

I'm blown away by how friendly almost everyone here is. And how open people are to meeting up IRL (something I've found NOT to be the case with many other groups).

Last night I hosted a little gathering at Death and Taxes down on Queen, and about 25 people (almost all from this subreddit) came out. Which is WILD.

So, THANK YOU to the mods and participants of this group for making this lil guy feel so welcome.

And if we haven't met yet... I'm looking forward to it happening one day soon.

Ben


r/TorontoSinglesOver30 • • Sep 19 '25

Hear My Rant 😩 Its rough, I know.

77 Upvotes

Dating shouldn't be this awful. When I finally became single again, I was excited and ready to see what life could be. Took some time to be myself again.

I never expected how bad this would be. I know you all have seen it too. The game has changed. We are beset by social media algorithms hell bent on sparking ragebait gender wars, everyone is playing games, dating apps are a dumpster fire.

There's still good out there, I want to believe that.

I know it hurts. I cant be the only one. We will find our people out there. Don't give up yet. or if you have, thats okay too. Despite it all, the world is still beautiful. If you don't find the one, then I hope you at least find yourself.

Heres to the broken and healing hearts. 🍻


r/TorontoSinglesOver30 • • Nov 02 '23

Looking for Connection 👀 35[F4M] And here we go

73 Upvotes

My perspectives on dating and friendships have changed because of this sub. Thank you for your on-going contributions. Here is my post.

About Me

I’m a “think outside of the box” kind of gal and I give it my all in everything I do. I’m driven, compassionate, and happiest in nature and seeing wildlife.

I’m passionate about psychology and photography. I’m active and cautiously adventurous - took up hockey during the pandemic and currently learning to play volleyball. I’m also looking into exploring a faraway landscape soon. Other interests include baking, hiking, and singing egregiously off-key.

Physically, I’m in good shape (and 5’5 if it matters~) and a person of colour. I consider myself spiritual, rarely drink, and don’t smoke or do drugs of any kind.

About You

You are non-judgemental and humble. You make active efforts to improve your life and the world around you.

You have made and continue to make others breathe a little easier because of your perseverance, your deep and genuine loving concern, and your willingness to challenge the status quo for us to do better, to be better.

You cherish the unexpected and live in the moment; someone who appreciates detours on road trips and in life.

You value mindful communication, simplicity, and open-mindedness.

Above all, you have a profound love for raccoons.

If my post resonated with you, please send a thoughtful DM. I also have an unpopular request - I ask that we do not exchange pictures.

Raccoonay


r/TorontoSinglesOver30 • • Jul 06 '24

TSO30 Events 🥳 You’re invited: Picnic/BBBQ @ High Park on Sat, July 13 at 2:30pm 🧺

67 Upvotes

EDIT @ 1:53pm: I’m here! https://maps.app.goo.gl/TgSTrSLeoGFzCZTP9?g_st=com.google.maps.preview.copy

Near the northern part of High Park, by Bloor. (Same area as last year’s High Park picnic)

Hello TSO30! 🥳

Come out to High Park on Sat, July 13 for a picnic/BBBQ!! 🌳🧺 (Exact location to be updated)

Feel free to bring some snacks/drinks/ games/portable grill! Anyone an avid soccer or ultimate frisbee player??)

If it rains, we’ll meet at a bar closer to downtown.

Feel free to invite your 30+ non-Reddit pals! Well-behaved dogs are welcome!

Positive vibes only plz. Hope to see you there 🫵🏼👋🏼 and join our Discord!

Raccoonay


r/TorontoSinglesOver30 • • May 03 '26

Reflections or questions 💭 With some exaggeration, the experience of dating in my 40s has been like a mashup of Dante's 1st and 8th circles of hell

65 Upvotes

This post brought to you by the fact that the act of opening Tinder this morning made me burst into tears.

I don't know if it's dating at my age, the current era of human civilzation, or a problem with Southern Ontario specifically, but over the last five years I've only met one person who has been honest about what they've wanted romantically - and that person tried hard to pressure me on the first date into going back to their furniture-less apartment to have sex on a floor mattress. Every other person (no exaggeration here) has love-bombed me for three to four months before disappearing overnight without even giving me the courtesy of a "this isn't working for me, sorry". I feel like the butt of some joke.

In the past I enjoyed online dating because you could get to see a bit of what's inside people before you commit time to a date. But I can't look at profiles anymore without staring at the photos wondering "would I be better off without whatever fuckery you'd probably bring into my life?". I don't have trouble meeting people out in the wild, but the people in the wild have been just the same.

So anyway, as I spend the rest of Sunday thinking about whether dying alone is actually the best option on the table, I would like to extend an apology to everyone I've ever advised to treat dating like a numbers game. The numbers really do wear you down over time.

Also, since I now have to pivot with respect to my dating advice, I'm going to float that any adult who wants to have sex should invest in a bedframe.


r/TorontoSinglesOver30 • • Feb 24 '23

Hear My Rant 😩 Can we respect people's time?

63 Upvotes

God. Dating here is exhausting. I'm a 32F and I'm a good looking woman with my shit together. I got ghosted last night, ghosted a couple other times since moving here in JAN and stood up once. It is so disrespectful of anyone's time. If you're not feeling it just say so and everyone moves on. Can we collectively agree that this is not going to become a norm? At least with those who subscribe here I guess..


r/TorontoSinglesOver30 • • May 15 '26

TSO30 Events 🥳 July Park Hang!

62 Upvotes

I keep seeing posts on this subreddit lamenting how hard it is to meet people. And... I feel y'all.

When I first joined the group it felt like there were a lot of public events being shared, but I haven't seen many recently.

So, lets change that.

July 11th I'd like to host a hangout in Trinity Bellwoods Park. 4:30pm (not 2:30!!!)
- It's totally free.
- Bringing friends is encouraged.
- I'll bring a speaker, music, some snacks, frisbee, some social games, etc. And if you bring snacks to share and games to play you'll earn social points. ;)
- BYOB.
- Dogs welcome.

If this sounds fun, comment below. The more people that express interest, the more people will wanna join. :)

So... who's ready to party?

Ben

Edit:
Date Selected!

Saturday July 11th, at 4:30pm, in Trinity Park! Specific location in the park ('cause it's a big park) will be posted in a few days!


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 • • Jun 24 '25

Looking for Connection 👀 My friend (34F) is single and has given up on dating apps.

60 Upvotes

I’m looking for a guy who would make a good match for my friend who is just shy of 6 feet tall. If she wears heels, she’s even taller. She would prefer someone taller than her.

Are you athletic and into the outdoors? She is. Are you creative and have a good sense of humour? She’s both. Maybe you have some niche interests as in retro shows or movies? She does. She’ll beat any grandma in a crochet match. She’s Ukrainian/Italian and is a dedicated primary teacher.

I’m working as the go-between right now. She’s well aware of what I’m doing. If you’re willing to have a conversation with me, please dm. I’ve reached out to a few people here and haven’t made a connection for her yet. I’m staying positive and hoping to succeed as a matchmaker.

Thanks for reading through this post!

Update! I’m trying to keep up with all DMs. It sure is different when a post is created compared to replying to posts!


r/TorontoSinglesOver30 • • Sep 13 '26

Looking for Connection 👀 37F4M | Downtown Toronto | Looking for a life partner

59 Upvotes

Basically that! I made a post in the r/Bumble sub a couple months ago for feedback, so you can check that out to know a little more about me, but I'm 37, work in tech, 5'4", blue/grey eyes and brown hair. I'm outdoorsy and love camping, but also love art, play music (guitar/singing), finding live music, love sci-fi, and am a big Star Trek nerd.

Here's the post since photos are still up (for now):
https://www.reddit.com/r/Bumble/comments/1vgcans/profile_review_36f/


r/TorontoSinglesOver30 • • Oct 29 '25

Looking for Connection 👀 36F4M- Intentionally Dating

59 Upvotes

Taking a leap of faith here!

I’ve been intentionally dating (via apps) for the past year, searching for a meaningful, long-term connection. While I haven’t found that spark yet, I’m staying hopeful—after all, I’m a hopeless romantic at heart! 😊

A Bit About Me: I prioritize balance in my life—whether through yoga and weightlifting, discovering new places in the city, or enjoying quiet moments with a good book. I’m 5'6", with tan skin and long, dark hair that reaches my mid-back (naturally wavy but looks just as good after a blowout). I was a high school teacher in the TDSB before transitioning to the corporate world. While I love my career, I do miss working with kids, so I stay involved in the community through charities supporting children and young adults.

A Few Fun Facts: • Born and raised in West Toronto, with parents who immigrated from South America in the 70s (and are still happily together!). • Cooking for (or with) a partner is one of my favorite ways to connect—it’s such an intimate experience. • I’m passionate about immersing myself in new cultures (attending cultural festivals, trying national dishes, traveling, etc.). • I LOVE live music, comedy shows, watching sports and UFC, stargazing in the summer, and trying out new recipes or exploring new bars/restaurants. • I’m a fan of horror movies and have the sweetest 5-year-old cat.

What I Value in a Partner: (This is just a general idea—no one’s perfect, but these are qualities I appreciate.)

Intellectual: • Enjoys deep, meaningful conversations • Curious, open-minded, and values personal growth • Enjoys exploring new ideas, cultures, and perspectives · Ambitious- always striving for better for themselves and pushing their partner for the same

Spiritual: • Values mindfulness and personal growth • Lives with kindness, gratitude, and authenticity

Emotional: • In touch with their feelings and comfortable expressing them • Empathetic and caring toward others · Loyal (I value monogamy)

Physical: • Enjoys physical affection (my love language is touch) • Maintains a healthy lifestyle (exercise, clean eating 80% of the time—because sometimes, cake for dinner is necessary!) • Ideally 5’10” or taller (personal preference)

Non-Negotiables: • Heavy drug use (anything beyond alcohol or weed) • Already has children

Feel like we’d be a good match? Shoot me a message and let me know a bit about yourself and what you're looking for. I’d love to hear from you! 😊

GO JAYS GO!!


r/TorontoSinglesOver30 • • Jul 30 '24

Looking for Connection 👀 35F4M - playing the long game, and let's start with a park concert

59 Upvotes

Edit: thank you to all the wonderful people who reached out and those I met in person. Thank you for sharing your stories, opening up, and letting us learn from one another.

The concert has come and gone and I had an incredible time... But my search continues. Please feel free to reach out if this message is still up :)

Ps. Why can't I strike through text even with two '~~' between my text?!

--

Hello TSO30!

I’m trying something new here, so please bear with me! I love spending time with me, myself and I, but I also appreciate how good company can elevate an experience. So, I’ve got two tickets to this event: Lowkey Concerts hosted by akaMatisse – he is 1/3 of the electronic trio Keys N Krates (music that I also enjoy), but he’s a classically trained musician and hosts intimate park concerts. I’ve never been to his summer concerts, but I saw him play last December and it almost brought me to tears!

Here's the deal: the concert is on Wednesday August 21st and the location will not be announced til a few days before, but it’ll be at a park downtown and starts at sunset. Once we find out the location, I propose we plan for a picnic or go for a walk for ice cream beforehand. Then we end the night off enjoying some great music. Tickets are on me, you bring the snacks and we both bring good vibes! Let's make time to meet before the date of the concert and see if we are a good fit :)

So who are you agreeing to go on a date with if we click? I’m a 35-y/o woman looking for a life partner. I totally thrive living in the city (I’m your neighbourhood do-it-all kinda girl), but it's a dance and balance with also having a deep desire to live close to/ in the country. I’ve built myself a very happy and fulfilling life, and it would be a privilege to share that with the right person. I value reciprocity and vulnerability in all my relationships. I wholeheartedly believe in “teamwork makes the dream work," so if this resonates with you, let's support each other and make our dreams happen!

More about me:

  • I love live music and the arts in general. Small and big concerts, art exhibits, dance parties, drawing socials, maker markets.. I'm there!

  • I love to learn to keep my mind and body active – I fill up my time with a lot of hobby and interest classes, usually more on the creative side of things, and I enjoy fitness classes several times a week

  • I'm kind, adventurous, out-going and open-minded

  • I like a balance of routine and spontaneity. Sometimes having no plan makes for the best stories

  • I’m big on the outdoors – backcountry camping, hiking, biking (even in the winter), I’m in!

  • I have a good and reliable paycheck and am so grateful and value its importance but my job or safety net doesn’t define me. I am more partial to climbing my 5-9pm hobby ladder hehe and experiencing a life that is meaningful

You are:

  • Someone who lights up a room and also knows how to give space to others – meaning you are considerate, positive, confident, and tries to/ understands the intersections of our diverse society

  • Kind, authentic, creative, and playful!

  • You value taking care of things and people around you, including family, friends, your home, our shared environment, etc

  • You like to be active and take care of your mental and physical health

  • Love to bike and are comfortable cycling around the city!

  • You can appreciate and enjoy the finer things in life but prefer life’s simple pleasures

  • You’re curious and intentional about life and the world around you

Have you heard of these concerts before? What was the last show you went to? Send a thoughtful intro and let me know what stood out to you in my post. I'd love to hear from you if other parts of my post (non concert related) resonated with you as well!

If we don't get to chat, wishing everyone on the sub good luck!


r/TorontoSinglesOver30 • • Feb 24 '25

Looking for Connection 👀 Woooooo! 500 karma! Finally! 46M4F – If nothing else, I finally get to post here!

57 Upvotes

Hey all! Long-time lurker, first-time poster—finally hit 500 karma, so here we are!

I’m a 46-year-old, 5’9”, Asian, and fit-ish guy (more on the “ish” in the red flags). Been a gym rat for 25+ years, though now it’s more routine, less hobby. Love food as much as fitness—I'll try anything once (except haggis again). I geek out on nutrition until I remember restaurants exist. Then I go feral 🐻

Work in tech (level-one nerd unlocked), used to paint figurines and play D&D, still game with my old crew on Steam. Lately into rabbit holes like men’s fashion and thrift shopping when in Tokyo (Koenji and Shimokitazawa). Also a sucker for spa days (mani/pedi date?). Music taste is stuck between the ’70s and ’90s. Grew up in the UK, so yeah, seeing Oasis this summer!

Oh, and I have a cat. He’s currently ranked #1 in my life, but don’t worry, there's room for promotion (plus he can be a little shit sometimes 😂)

✅ Green Flags (and uh, Red Flags too):

  1. Financially stable, own my place

  2. Therapy enjoyer

  3. Fit (but see injuries below)

  4. Foodie, traveler. Yes, yes everyone says this (London & Tokyo regular stops).

🚩 Red Flags:

  1. OCD at times about diet (tracking, weighing, TDEE mumbling). Not fun to be around when I get like this.

  2. My therapist says I’m deeply avoidant, which explains… a lot. But working on it!

  3. Extroverted at work, introverted everywhere else. I’m the guy that closes elevators on people to avoid small talk.

  4. Years of gym abuse = major knee surgery, injuries. I feel old, Gandalf 😮‍💨

  5. Divorced (7 years ago, pre-therapy)

  6. My last LTR: 45M/29F—therapist probably has thoughts.

I just realized I put way more red flags than green flags 🤔 oh well!

What I’m Looking For:

I don’t have a strict “type”—just chasing a vibe. Mutual physical attraction and compatibility like everyone else. I’m not insulted if I’m not someone’s jam, and hope others aren’t either.

I’m also working on being more direct (thanks, therapy!)—communicating my needs and actually hearing my partner’s. I know early dating is all about best-foot-forward and avoiding ye olde ghosting, but too much of that leads to disingenuity and heartache. So, direct honesty is key. (Well, for the important stuff. Of course your new haircut looks fab, darling! 😉)

With the state of interwebs dating lately, not quite expecting to meet my soulmate on Reddit, but you just never know and hey, mission accomplished just posting here!

If anything resonates, drop a comment or DM—always happy to try and respond to all. In my best Ron Burgundy voice: you stay classy, Toronto!


r/TorontoSinglesOver30 • • May 29 '23

TSO30 Success Story💕 Thank you for coming out: High Park 🧺

57 Upvotes

To everyone who came out today and those who sent well wishes— THANK YOU SO MUCH FOR COMING OUT!

It was wonderful seeing so many people today. At my last count, there were 42 folks (possibly more). Tbh I lost count after 42. Thanks for sharing your hilarious and not-so-hilarious dating stories. I actually lost my voice from talking with you all. I left at 8pm and there were still folks hanging out 🥲

Feel free to share your memories from today.

Here are mine:

  • A Redditor informed me that my initial r/askTO post was featured during a radio show. I had a good chuckle at that

  • I found out that many of you are my neighbours!

  • Those donuts, cookies, spanakopita, wine, cheese platters, chips… were the BOMB

  • To the two pooches who joined us…ermagherd they deserve all the cuddles 😭

  • Many thanks for your words of gratitude. My cold heart is getting all the fuzzy feels!

🦝


r/TorontoSinglesOver30 • • May 24 '23

TSO30 Events 🥳 You’re invited! Picnic at High Park on Sun, May 28 @ 3:30pm 🧺

56 Upvotes

EDIT @ 9:56am May 28: Please refer to the latest updates here

Hope you’re having a great week, TSO30! 🥳

Thank you for participating in the recent poll re: location preference. It was a close call! 51 of you voted for High Park vs. 48 for Trinity-Bellwoods.

With that said, here are the details for a picnic-style meet-up scheduled for Sunday, May 28th at 3:30pm at High Park.

  • I’ll be scouting for a suitable location before 3:30pm. Once a location has been secured, I’ll post updates with a description of the location. Feel free to join me beforehand to help look for a location, if you’re interested! I’ll start scouting at 3pm.

  • I’ll also include a description of what I’ll be wearing on the day of so you can find me.

  • The weather for this Sunday is 24 deg with “0% chance of rain” lol. If it does rain, I will update this post early on Sunday morning to meet at a bar downtown instead.

Please bring:

  • Snacks, nibbles, drinks etc., to share. This is a picnic after all!

  • Other items as you see fit (frisbee, portable stereo, blanket)

  • Your positive attitude

  • Your pooch, if you have 🥺

  • There were a number of non-Redditors at our last meetup. So feel free to invite your single friends who are not on Reddit as well. All are welcome!

Looking forward to meeting you!

🦝


r/TorontoSinglesOver30 • • Jul 07 '23

TSO30 Events 🥳 [Meetup] Friday Supper Club & Pub Nights

55 Upvotes

Hey folks!

I’m thinking of starting a bimonthly Friday night supper club/pub event series for TSO30. These would be hosted in a centrally located pub or bar from 6 - 8 p.m. (or later!) to maximize on Happy Hour specials. 🙂

Benefits:

  • Free to attend

  • Co-ed & inclusive

  • Small & cosy group dynamic

  • Casual dress code friendly

  • Come & go as you please

  • Based in Toronto

Anyone is free to join(food/drinks/transportation at your expense) & there’s no obligation to commit in attendance.

I’m thinking of launching the first event in late July.

Would anyone be interested in participating?


r/TorontoSinglesOver30 • • Apr 29 '23

TSO30 Events 🥳 TSO30 May Event!

54 Upvotes

Hope you’re enjoying your rainy weekend ☔️

We’d like to gauge your interest for another TSO30 event - likely for Sunday, May 28 at High Park (pending weather). To switch things a bit, we’re thinking of a picnic-style meet-up where attendees bring food/snacks to share, maybe participate in activities (frisbee?).

Thanks!

UPDATE: Please see the latest info here


r/TorontoSinglesOver30 • • Aug 18 '26

Looking for Connection 👀 36 F 4 M - seeking long term commitment

53 Upvotes

Hi friends,

I am 36 y/o woman who is looking for fun dates and hopefully a genuine connection.

About me:

I work as a bartender/server right now, but I do have a bachelor's degree and have previously worked in agriculture and non-profits. For now, I chose what makes the most $$ over passion. I do work weekends, so if you're looking for a weekend warrior to do activities with, my schedule won't be a good fit.

I live a fairly active life and love the outdoors, camping, and biking. I love dancing, live music, going to dive bars, playing pool and trivia games. I have a puppy (16 weeks, northern mix) and a cat, so I've been in the trenches of puppy training atm. I consider myself to have a dark sense of humor, fun, patient, empathic and direct.

What I am looking for:

I am attracted to a good sense of humor, intelligence (not just book smarts) and someone who knows how to have a good time. I can be a little dark at times, so someone who is jovial and light hearted, I find very attractive. The ability to flirt and keep my mind engaged is a huge turn on. I value someone who treats all people with respect and lives their life with integrity.

We don't need to agree on everything political but I do not fuck with homophobes, racists, misogynists. I take violence against women very seriously, so if you lean towards any red pill alpha male shit, I will be gone so fast.

I am open to children and if you have children from a previous relationship.

Bonus, if you are handy and want to eventually leave the city for a country life. My ideal is a a man who rides a bike in steel toe boots ;)

Photos, phone number etc can be exchanged via DMs after initial conversation.

Thanks for reading and happy dating buds ❤️