10 Great Locations to Meet Single Cougars in Winnipeg in 2023

Lots of cougars in Winnipeg are professionals who know how to have a good time

As a culturally diverse city, there are a lot of opportunities for you to meet older women from different backgrounds here in Winnipeg. It may be dubbed as the “Windy City”, but the cougars in Winnipeg remain red-hot if you know where to find them.

From downtown bars and eateries to neighborhoods like the Forks, you’ll never run out of spots to mix and mingle with lovely mature ladies. Because no matter your scene, the diversity of Winnipeg will serve you well. All that’s left for you to do is to know where to find these Winnipeg cougars!

Below we’ve mapped out a few Winnipeg cougar bars along with other spots where you will likely meet a sexy older woman. Get ready to charm these cougars with your moves. And if you know of any other spots that should be on this list, let us know all about it in the comments below!

Where Single Cougars in Winnipeg Go

Our team of experts hit the streets of Winnipeg to find out where the hottest cougars hang out. Each place is full of fun and opportunity. We think you’ll be quite happy with what they found.

Have a crazy, fun night at the Palomino Club

Beautiful women having drinks at Palomino Club


If you're looking for a club with a packed dance floor and a crazy crowd, then the Palomino Club is your best bet. Here you'll find good food, affordable drinks, friendly staff and even friendlier older women.

Prepare for a night of dancing, jamming and drinking. Most locals will agree that it is one of the most usually frequented clubs by cougars who want to meet some guys. You might not even have to put any effort at all because they'll be the one to go after you.

If you want a quieter place to have a conversation, then head downstairs and shoot some pool with your date. But if you're looking for a crazier night, go on a Monday to catch the “Booty Shake” event where ladies compete to win 500 bucks!

AFF is where we’ve seen the most success finding cougars that just want something casual or physical (try it free)

Homepage for AFFIf you’re looking for cougars in Winnipeg, then you need to try AFF (which has a great free trial). We have tried out just about every app and site out there, but only AFF actually delivers consistently. That's not surprising because they've been in the game since 2006.

Guys who haven't had the best results elsewhere and actually want to find some success with local cougars need to check out AFF!

The great thing about AFF is that you'll mostly meet older women. Most users are aged 30 and up. So you know you have great odds of meeting some mature older ladies here. On top of that, all these women are after casual encounters. No romance needed; just a naughty night of fun.

Try AFF and see how easy it is to get laid in Winnipeg!

Try AFF For Free!
If you actually want to meet single cougars who are more interested in fun in the bedroom than a long-term relationship you need to check out AFFs free trial with this link. We've spent many months testing out 100+ different sites and apps to meet cougars and AFF has consistently been the easiest way for most men.


Citizen Dance Club is the place for nightlife lovers

The full dance floor at Citizen Dance Club


Citizen has many faces. You can go there for the food, for the happy hour, to go clubbing or to meet single older ladies. Why don't you stop by after work and make the most out of their happy hour deals? Citizen offers appetizers, wine, beer and more for only $5 from Tuesday to Friday, 5 to 7 p.m.! This is the best time to run into some older women who just got off work.

It shouldn't be a surprise that a lot of women love to dance. In fact, there are few places better for finding a single cougar than a fun dance club that isn't too pretentious.

Apart from the affordable food, old school music fanatics will enjoy the club's playlist as it mostly consists of throwback and Top 40 hits. No wonder the cougars of Winnipeg love this place! So practice your dance movies and maybe learn a few new ones, so you can show these cougars what you've got!

Cougars in Winnipeg like eHarmony when they want long-term relationships (try it now)

eharmony.com homepageWe’ve tested a lot of dating sites and apps to meet cougars and if you haven't tried it out yet (or it's been a while) eHarmony is the absolute best quality option we’ve seen to get results in Winnipeg. This is especially true if you want to meet older single women, as these women tend to have a lot going on and they don’t always have time to be out looking for men. When they do want to meet guys, many of them turn to online dating because it’s often all they have time for. eHarmony happens to be a favorite among these cougars for good reason. There’s even a proven trial that we highly encourage you to sign up for.

So, what exactly is it that sets eHarmony apart from other sites and apps? We know Tinder is really popular, but good luck finding older women on there. eHarmony has been around a bit longer than most other options and is very well known. cougars tend to go with the option that is proven and they can trust, not the flashiest new app or site. That means a lot of eHarmony's 30,000,000+ members are exactly what you're looking for.

eHarmony’s matching process is also much more unique and it starts with the lengthier profile questions required of members at signup. Believe us when we tell you that this is actually a very good thing (so don't be scared off). We know most of the women that make it through the signup process are motivated to find men because they’ve actually taken the time to complete their profiles.

You’re not likely to find many members who are just casually browsing the site because it is a little bit of a time commitment up front (even though it really isn't THAT long). It also means you’ll have more compatible matches because eHarmony is going to help you match with women based on their answers and not the number of hot selfies they’ve posted (hello, Tinder).

They're so good in fact that nearly 3/4ths of all marriages that start online started with an eHarmony match!

We could easily go on and on about why eHarmony is a great option (did we mention 15 million matches are created a day on the site?) but why don’t you just see for yourself? Sign up for their proven trial today and start meeting the many cougars in Winnipeg who are using it. You won’t be disappointed.

Don't expect to get great results without trying something different in your approach!

eHarmony trial

You won't feel lonely at Times Changed High & Lonesome Club

Friends having drinks at Times Changed High and Lonesome Club


Located at 234 Main Street, this dive bar is an iconic venue where many legendary acts have stopped by over the years! If you're looking for something that is a bit different and offers quirky fun, then this is the place to be.

High & Lonesome club is also popular for their tasty yet inexpensive quesadillas. They can accommodate vegans as well which is probably why a lot of cougar hippies are drawn to the place. Check out the comedy open mic and music every Thursday and you might just meet someone fun with a great sense of humor.

Feel right at home at this dive bar as you get cozy with some cougars. And the best part is that you don't have to spend a ton to have a good time. So head over to High & Lonesome--you won't be lonesome for long!

Cougar dating promo

Find a fit cougar at Reh-Fit Centre

An aerobics class at Reh-Fit


The newly renovated Reh-Fit Centre will let you kill two birds with one stone. Not only can you tone your muscles, but you can find also yourself a fit cougar while you’re at it. Compliment a cougar on the workout routine or ask them for help using the equipment. Offer to be her spotter and if she finds your gesture adorable enough, then she may just ask you to take them to lunch at the chic on-site café.

The Apps Dating Coaches Recommend Most To Meet Cougars

More and more older women are only using apps and sites to meet guys, especially younger guys. You need to be on at least one or two apps now if you want to get the best results you can. These are the apps that give normal guys the best success meeting cougars:

SiteOur ExperienceOur RatingFree Trial Link
Best Hookup Site Cougars
Experience Highlights
Experience Highlights
  • The best way to meet cougars for hookups by far
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
2nd Best For Hookups
Experience Highlights
Experience Highlights
  • 2nd best option to find hookups
  • Attracts an older crowd than most hookup apps
  • Pretty popular
  • Great free trial
Try Passion

Find a food-loving cougar at De Luca’s Cooking Classes

Mini burgers from De Luca's Cooking Class


Where better to take a cooking class than in a gourmet grocery store? And where better to find a cougar than in a gourmet cooking class? De Luca’s public cooking classes put their main focus on quality. Their secondary focus? Fun.

The wine tastings and the aroma of classic Italian cooking all around turn everyone into a romantic. Make your food, eat it too and find a cougar in the process. It’s a win-win-win situation.

Course promo

Find a sporty cougar at Winnipeg Rec League

Friends drinking in a tent at Winnipeg Rec League


People have been bonding over sports since the beginning of time and Winnipeg Rec League is great for making that happen. The leagues focus more on being social than being competitive. That being said, it’s also perfect for mixing and mingling with tons of cougars in Winnipeg.

Choose the sport you love most, and you’ll find mature, sporty women who share your passion. Flirt with them on the field, and get to know them a little better over discounted drinks at one of the sponsors’ pubs. One could say that you’ll create a connection to last a lifetime.

Cougars in Winnipeg sitting in the sun outside Winnipeg Art Gallery


The impressively large WAG is home not only to some wonderfully historical works of art, but some wonderfully intelligent, mature, and sophisticated women too. A quick stroll through their halls will show you all of the beautiful art Winnipeg has to offer. And especially in the way of their women.

Strike up a conversation about a piece a cougar seems to admire. Ask them what they think it means, or their opinion on the use of colours. They’ll be happy to share some ideas. She might want to discuss art further over some coffee, but only if you're up for it.

Some of Our Favorite Cougar Bars in Winnipeg

The suggestions above are great, but you also need to check out these bars.

Find a classy cougar at HY’s Steakhouse & Cocktail Bar

A steak and lobster tail from Hy's Steakhouse


The cougars in Winnipeg love to flock to this high-end restaurant, which is just a stroll away from the bustling intersection of Portage and Main. As you walk into this place, you’ll notice the high ceilings and gorgeous dark wood. The atmosphere oozes class and style, and the restaurant guests reflect similar attributes.

Chat with cougars at the bar over fine wine and whiskey or bring a cougar here for an evening she’ll never forget. It will also show her that you’re a man of great taste.

Single woman

Meet feisty cougars at the Yellow Dog Tavern

Outside The Yellow Dog


The delicious dishes in their daily features have lured many a tavern-lover to this spot. But while they come here for the food and drinks, you should drop by for the crowd. This laidback spot has lots of cougars--both regulars and new faces. You'll find them sitting at the bar or enjoying front-row seats to the live piano performances.

Yellow Dog Tavern ensures you always have a fun night. That's probably why the beers are cheap, the cocktails are strong and the crowd is lively. Every night you visit is always interesting, and it gets even more interesting when you make a new cougar friend!

For more recommendations check out more great guides to meet cougars:

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