Canadian MILFs tend to be mature and laidback, with a passion for the outdoors. They also care about their health and staying fit. For those who have never been to Canada or don’t know anyone from there, you’ll have the additional benefit of learning about a new culture when you date a Canadian MILF.
However, you might be wondering about how to find single Canadian MILFs in the first place. They can be tough to come across when you’re at your usual bar or pub, surrounded mostly by women in their 20s. If you simply sit back and wait, you’ll be lucky to find even one!
Trial and error won’t cut it here--you’ll need a more targeted approach to form a romantic connection with these MILFs. The key is to look for MILFs in the right places. Older Canadian women often go to certain hotspots, and they’ll be in the mood here to flirt and check out younger guys.
If you’re interested in dating one of these sweet yet strong older women, we’ve whipped up a list of destinations where you’re likely to run into an attractive Canadian MILF. Head to any of these while putting your best foot forward, and you might be going home afterwards with a Canadian MILF’s number.
Get out there and start mingling with Canadian MILFs! We’re always open to comments, so feel free to share your experiences below.
Proven Spots to Meet Canadian MILFs
Head to these spots first to meet the MILF of your dreams! Let us know how it all goes in the comments below.
Socialize with Canadian MILFs through Connect2Canada
Hanging out at bars and maximizing your nightlife can help you snag a Canadian MILF fast. But you can also try going to events featuring Canadian culture. Aside from looking out for concerts by Canadian musicians, book signings by Canadian authors, and so on, try checking the events page of Connect2Canada for a quick list.
While Connect2Canada is located in Washington DC, it features activities from all over the country. For example, you can go to a film festival, an art exhibit or even hockey games.
The events are pretty diverse, so you’re sure to find at least one that appeals to you. Even better, the Canadian MILFs you’ll meet here are likely to share your interests. This gives you an instant way to start the conversation, and you can easily ask her out to related events in the future.
Conveniently, many of the people you’ll run into here will be Canadians or locals who are friends with Canadians. You can enlist their help as matchmakers--they might know a single Canadian older woman who’d love to see a younger guy like you.
The easiest way to meet MILFs that want to keep it casual and physical has been AFF (which has a free trial)
Meeting Canadian MILFs who are interested in something casual is not always easy. Either you end up meeting the ones who want a relationship or you always meet much younger women. If getting some action is on your mind and you only want to be with older women, AFF (which has a great free trial) is the site for you.
We tried a bunch of different sites but had the most success meeting older women with this one. Unlike apps like Tinder, Aff was built for people looking exclusively for some casual fun. Nothing serious, just seriously fun. Skip over all the awkward small talk and expensive dates and get straight to the point with women who want the same thing.
When it comes to sites that actually deliver AFF has been in a category all its own for us. We have seen way more “normal guys” find success using it than any other site or app, at least when it comes to getting some action. The success rate combined with their free trial make it a pretty obvious choice to at least checkout.
They have been around since 2006 and they have built quite a reputation. A reputation that’s attracted over 50 million members. It is the largest site of its kind, which means you have plenty of chances to woo beautiful, mature women. Other dating sites have become dominated by younger women in their 20s who are not serious about actually meeting up. They are just looking for validation and some attention. But on AFF, the MILFs you’ll find are pretty keen to get down to business.
So instead of spending your Saturday nights wasting time and money trying to pick up women in bars, do yourself a favor and join AFF. They have a free trial, which makes it easy to see what kind of women are in your area and all that the app has to offer. Work it into your day-to-day life and your chances of getting into bed with a woman will seriously increase.
Explore beers with Canadian MILFs at breweries
With hundreds of breweries in Canada, many Canadian MILFs are huge fans of high-quality beer. If you’re a beer lover yourself, then you might meet your Canadian MILF match at a brewery.
You’ll not only get to taste good beer straight from the source, but you’ll also see the process behind how it’s created and stumble on new craft beers you’ve never tasted before! Of course, the highlight here would still be the attractive older women who’ll be there with you.
Gauge whether you have any chemistry by asking a Canadian MIlF what beer she likes so far. If she’s interested in you, she’ll eventually give you flirty responses. We’ve heard about guys meeting MILFs this way and sharing a meal afterwards just to continue the conversation.
Tours are great because socializing comes more naturally. Since you’ll be exploring the brewery together, you’ll have several opportunities to chat her up. Choosing breweries in cities that are close to Canada can increase your chances. Washington, Maine and New York share a border with Canada, so Canadian MILFs often visit here. Canada also holds the Cask Days Beer Festival every October in Toronto if you’d like to travel further!
eHarmony makes finding a Canadian MILF for a relationship easy
We have found that eHarmony is one of the best places to meet Canadian MILFs (you can try them for with this offer). You can tell from the website's top-notch design that it's a serious place for finding an older woman to date.
We have also noticed that the highest number of attractive MILFs tend to be on eHarmony. This website offers helpful features, such as Find a Date Tonight, assisting you in connecting with an older woman. Every year we rank and review all the best sites to meet MILFs and they have been the best for a while.
You can quickly schedule a coffee or bar date with the Find a Date Tonight feature. Just remember to take them somewhere classy and upscale if you're going out for a drink.
Have a romantic time at ski resorts
Canada is known for its notoriously cold weather as well as rugged terrains, making it perfect for ski resorts and winter hobbies. The largest ski resort in all of North America is actually in Canada, and there are several more ski towns such as Mont Tremblant and Big White.
Still, Canadian MILFs who enjoy skiing are often curious about ski towns in other countries. For younger guys who want to indulge a bit this winter, ski resorts might be the place where you’ll run into the right Canadian MILF. Park City Mountain Resort in Utah, Jackson Hole Mountain Resort in Wyoming, and Vail in Colorado are some ski resorts that are popular among Canadian tourists.
Many ski resorts also welcome beginners. So regardless of your experience with skiing, this can work for you! Bars and hot tubs can get you socializing right away with any Canadian MILFs around. Ski resorts typically have social activities, from hardcore partying in their bars to comfy singalongs.
Ski resorts also have a captivating ambiance, complete with a stunning view of the mountains, winter all around and the cozy warmth of fireplaces or a steaming drink. They’re ideal for starting a romance!
Coffee shops are a great place to look for Canadian MILFs
Starbucks and other coffee shops are always a good place for finding Canadian MILFs. The best time for finding older women at coffee shops is in the early morning. Businesswomen often grab a cup of coffee before heading to work. If you're interested in businesswomen, you'll want to start visiting coffee shops in the early morning too.
But how do you get to know one of these busy women here if they're on their way to work? We advise that you engage in idle conversation. Ask her if she goes there often and which drink she recommends. Continue going to the same coffee shop in the early mornings if she said she goes there often so you can chat again.
Perhaps you could let her know how you liked her coffee recommendation and continue the short conversation from there. After a few times of running into each other, she'll feel more comfortable giving you her number if she's also interested in you.
See Canadian MILFs regularly at night classes
MILFs are obviously busy during the day working or taking care of their kids. So you won't find many of them at colleges during the day. You will, however, easily find a Canadian MILF at night classes. Only try this option if you're interested in furthering your education and you can make time for attending a night class.
You don't want to pick a subject that bores you just to meet single MILFs without the competition from other guys. Always choose a subject that excites you or would boost your career. If you've been toying with the thought of a career change, you could kill two birds with one stone by signing up for night classes.
Not only will you learn more about a subject you're considering pursuing as a career, but you also position yourself in a hotspot for MILFs. Just don't let yourself get too distracted during class if you spot a sexy Canadian MILF.
Dating Apps Dating Coaches Recommend to Meet Canandian MILFs
More than ever before women, especially older women and women with kids, are using dating apps to meet guys. They're too busy to go out to bars and clubs so they primarily meet guys this way. If you want to get the best results with them these are the top dating apps to meet them right now:
| Site | Our Experience | Our Rating | Free Trial Link |
|---|---|---|---|
Best For Relationships  | Experience Highlights
| 9 | Try eHarmony |
Best For Casual Fun  | Experience Highlights
| 9 | Try AFF For Free |
Decent For Younger Guys  | Cougar Life Highlights
| 8 | Try Cougar Life |
Restaurants with bars are classic hangouts for Canadian older women
Do you happen to be in need of a part-time job as well as a Canadian MILF? Apply for jobs as a waiter or bartender at restaurants with bars. MILFs frequent these types of restaurants, and as an employee there, you'll have plenty of opportunities to connect with one of them.
Because you’ll be working at the restaurant, you might become familiar with the MILF regulars. You can check if you have sparks by asking her what she thinks about the restaurant and letting the conversation flow from there. If you hit it off and she starts acting flirty, don't be afraid to ask for her number.
Upscale bars attract Canadian MILFs
A bar is one of the best places to look for a one-night stand or short fling. We think it's a good way to test whether or not you'd really be into older women are not. Some younger guys want to try dating a Canadian cougar or MILF, but aren't entirely sure if it's for them. Others just want to have a no-strings-attached night with a Canadian MILF.
Either way, upscale bars are more popular among mature women. And if you play your cards right, you might end up on doing more than just drinking if you run into a single MILF!
Gyms also have a lot of Canadian MILFs
Be a bit more cautious with this location because some women don't enjoy being hit on while at the gym. Pay attention to her body language when you approach her and keep the conversation casual at first. We've written a guide about how to find MILFs, and gyms are always a good place to try, especially if you're in shape yourself.
If she doesn't seem open to talking, then go back to working out. Then wait until you notice another MILF you're attracted to. After seeing the same woman at the gym a few times and having a few brief conversations with her, ask her if she'd like to go out for coffee afterward.
Sweat it out with Canadian MILFs on jogging trails
If you enjoy running or jogging, then jogging trails are a good place to find MILFs. Test out different jogging trails in your area until you find one that seems to have more older women. See a MILF pass by that you're interested in? Jog beside her and engage in small talk. Once you've found a MILF that you may have a chance with, jog in the same area for your routine cardio exercise.
As we usually recommend, talk to her a few times until she warms up to you. It can turn what would have been a "no" into a "yes.
Expand your horizons through cruises or island vacations
Going on cruises or island vacations is another good way to find MILFs. Single older women tend to go on vacation alone or with a group of friends. The next time you go on a cruise or island vacation, keep your eyes open for a MILF who seems open to chatting.
She'll usually be more receptive to getting to know you because she'll be in the mindset of letting loose and having fun while on vacation. The unfamiliar scenery also adds to the romance and will help make you more memorable to her.
Visit the top destinations among Canadian travelers
Unless you're lucky enough to live in one of the top destinations where Canadians go on vacation, you could always visit those cities yourself. According to Global News, a Canadian news site, the top 10 most popular international vacation destinations among Canadians are:
- New York City
- Las Vegas
- London
- Paris
- Orlando, Florida
- Chicago
- Los Angeles
- San Francisco
- Seattle
- Rome
Be conscious of Canadian MILFs in middle- or upper-class neighborhoods
Many Canadian MILFs live in middle to upper-class neighborhoods. You could even rent or buy a place there if you’re that serious about meeting these MILFs! But if you can't afford to move into the neighborhood yet or you don't want to give up your current home, you could take a walk through a neighborhood where you'll find MILFs. A lot of them will be married, but you'll still be able to find some who are single.
You can start a conversation with a Canadian MILF by asking for directions to a nearby store. Always be casual and don't loiter anywhere. You wouldn't want someone calling the cops on you because you're sitting in your car on the side of the street.
Sexy Canadian MILFs are often customers at health food stores
If you want to find a Canadian MILF who cares about her health, fo to a health food store. MILFs who shop at health food stores are often fit and will be willing to cook healthy meals for you once your relationship progresses.
You can easily strike up a conversation with a MILF at a grocery store by asking her for recommendations on meals you could make with a particular fruit or vegetable. After listening to her advice, you could flirt by saying it looks like you can now make her a nice dinner. In case she isn't familiar enough with the produce, you can ask if she'd like to get together and make a meal using that ingredient.
Cross paths with Canadian MILFs at high-end malls
Another area where you'll find Canadian MILFs is high-end malls. They enjoy shopping for themselves and their children. You could ask them for advice on a gift to buy your niece or nephew. Alternatively, you could ask them which dress shirt looks better on you for a family member's birthday dinner.
Only ask if you're being genuine. For example, if you don't even have a niece, don't pretend like you do. You could also buy something to donate to a charity if you don't have a current need to buy gifts. A charitable man is always attractive to a Canadian MILF.
Tea rooms are a Canadian MILF favorite
A lot of tea rooms have an upscale, relaxing atmosphere, so you'll find MILFs here too. Tea rooms are small cafes or restaurants that serve tea and light refreshments. Canadian MILFs who enjoy drinking tea will go here to relax and have some time to themselves. They may also go with a friend.
If you see an older woman you're interested in, you can talk about how it's your first time at a tea room and ask for her recommendations. This signals to her that you’re open to talking. A Canadian MILF who’s interested in you will even invite you to sit with her. Or she might drop by your table to continue your chat.
Visit Canada to encounter diverse MILFs
This last spot is for those who don't already live in Canada. Yes, it's obvious, but we still thought to remind you to visit Canada. Even if you don't find a MILF you hit it off with during your stay, you’ll at least have stories to talk about when you meet a beautiful Canadian MILF online or somewhere else. She'll be excited to hear that you've been to Canada, and she’ll want to know what you think of her home country!
For even more options for meeting single MILFs check out our other guides:
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