12 Great Bars and Spots To Meet Single Cougars in Milwaukee in 2021

Beautiful woman in the city

Are you looking to meet or date cougars in Milwaukee? You’re in luck because the older women in our city are as beautiful (if not more) as our city. You’ll love the local social scene because everyone is more open and adventurous now.

Single Milwaukee cougars freely go out with younger men these days. Cougar bars are also booming because of young men and cougars who want to connect. Cougar bars in our city may not be as abundant compared to other bustling cities, but there are some really great cougar hangouts here. Now it’s up to us to let you know which ones are worth a visit.

We have quite a number of establishments that are perfect for finding a potential date. Whether it’s Downtown, Washington Heights or Lower East Side, there’s a great cougar spot waiting to be explored.

Don't waste your time at boring places and check out our favorites below.

Best cougar bar in Milwaukee for guys

Mix romance and fun at this cougar bar where we always manage to meet beautiful older women!

The Outsider is a swanky rooftop bar with lots of interested mature women in Milwaukee

A woman having a drink at Outsider Rooftop Bar


The Outside is a hidden gem that not many people know about. The rooftop bar is settled on the ninth floor of Kimpton's Journeyman Hotel. The bar is definitely classier than most and you’ll find that this place attracts gorgeous single women who aren’t looking to play games. This Milwaukee cougar bar also offers up a great variety of wines, cocktails and beers if you need some liquid confidence.

The rooftop bar has both indoor and outdoor space, making it a great go-to no matter the weather. The views from the bar are indescribable and many women come here to take the perfect selfie with their friends. We definitely recommend coming here dressed a bit fancier than you would to a dive bar. From there it’s all about positioning yourself for the perfect icebreaker with a gorgeous woman.

Where to meet cougars in Milwaukee online

Going online might just be the easiest way for you to meet cougars. But if you don't know where to start, here's what we recommend.

Meeting a hot single cougar on Adult FriendFinder for bedroom fun is our favorite (try it free)

Homepage for Adult FriendFinderIt’s not hard to get laid in Milwaukee, especially if you go to all the right places. The problem arises if you don’t have the time (or the cash) to go out every night hunting for horny cougars. The solution? Adult FriendFinder.

No other site boasts a bigger number of frisky singles who just want to get laid. On this site, you’ll meet all sorts of people who are looking for some naughty fun between the sheets. And don’t worry; everyone here knows what’s up. So you won’t have to cringe through another awkward goodbye as you “promise” to go on another “date.”

We've tried a lot of different options and this has been the simplest way to meet cougars to take home fast!

The best thing about Adult FriendFinder is that the majority of its users are over 30. Sure, you’ll run into the occasional 20-something, but you’ll mostly meet older women here. So give the site a shot and you could start getting laid tonight.

Try Adult FriendFinder 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 Adult FriendFinder's 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.


Cougar Life is by far, the best Milwaukee cougar dating site for finding some romance (try it free)

Homepage for Cougar Life

There are several great options to meet more mature women when you're going out but you only have so much time and money you can spend. If you REALLY want to meet a lot of single cougars you need to be smart and efficient with your time. That means checking out Cougar Life's free trial.

A lot of cougars have stopped spending time in bars and clubs and ONLY meeting single guys online. They're busy too and being able to connect with men, especially when they want to date younger guys, makes their life (and your life) a LOT easier.

If you haven't tried out online dating yet to meet cougars you're missing out on a TON of opportunities!

There are a few reasons why we've found Cougar Life to be the best option for most guys and why it's at the top of our rankings for the best cougar dating apps and sites:

You won't find more Milwaukee cougars on any other site or app

There are other options out there that have more people using them but actually finding single cougars can be very time-consuming. Even if you find attractive women over 35 using them you never really know if they're interested in dating younger guys.

With Cougar Life, every woman using it is VERY open to dating both younger and older guys and they aren't afraid to show it! No other option out there has more REAL COUGARS that you can actually meet up with.

Younger guys won't do better anywhere else

Cougar Life is great for older guys who want to date cougars but younger guys will be especially pleased with it. There is still a big stigma with women about dating younger guys in a lot of places and Cougar Life does a great job of making women feel comfortable with their desires.

No other option comes anywhere close to being as effective for guys who want to date older women!

Instead of worrying that the women you're messaging MIGHT be interested in a younger guy you know she is. Don't be surprised if you actually get older women messaging you first for once either!

These women actually want to meet up and there's a great variety

It doesn't matter how many people are using an app or site if all the women are just there for attention. Most of the bigger free apps out there are filled with time-wasting women who just want to collect compliments.

In our experience, the women on Cougar Life are MUCH more engaged and actually want to meet guys in person. Why else would they use such a specific site? There is also a great mix of women who want short-term fun and those who want an actual relationship. You can pick and choose.

If you haven't tried out Cougar Life's free trial you absolutely should. It's a great experience for most guys and a combination of time spend in our favorite places on this list and Cougar Life is a recipe for success!

Top Milwaukee cougar bars you have to try

Cougars love going to bars to catch up with friends, grab some drinks and maybe meet someone special. You might ger lucky at these spots.

Downtown bars to find cougars in Milwaukee

Downtown is where older women go to drink after working in the city. Here's where we usually find them.

SafeHouse: for James Bond wannabes hoping to capture irresistible cougars

A couple of mature women at SafeHouse


Mature women love this theme bar because they can geek out to their inner spies. It will charm you with its fun ambiance of a 1920s speakeasy. It’s definitely the place to be on Friday nights.

There are so many areas to explore, though you need to find the right password to gain access to the place. That’s part of the fun of searching for hot older women (who might also be sexy spies!). If you’ve always wanted to be a spy, you will have a field day at this pub. Come up with the most kickass agent name and clear the missions before your orders arrive.

There are fun menu items, like Spy’s Demise (a Long Island with cola and blackberry liqueur) or Man with a Copper Mug (Stoli Vodka, soda, ginger, and fresh lime juice) and the Great Spytini (vodka martini). It’s one of the coolest Milwaukee cougar bars, and you will not be disappointed by the women you’ll meet here. If you’re lucky, you can clear different missions together and see where the night takes you.

Elsa’s On The Park is a swanky bar that cougars love

Located at 833 N. Jefferson Street, this swanky bar and restaurant draws in many women looking to unwind. Elsa’s on the Park has a chic and intimate Euro café feel that goes well with their American/Italian-inspired menu. It’s a Milwaukee staple, so don’t be surprised if the place is packed even on off-peak hours.

The bestsellers here are the nachos, burgers and bacon grilled cheese sandwiches. If you’re on a healthy streak, they also have the guilt-free pork teriyaki salad. The burgers are big and the drinks are delightful.

Keep your eyes peeled for cougars who pop by on their lunch breaks or have a martini after work. Elsa’s stretches cocktail service from Sunday to Thursday until 1:30 a.m., and until 2 a.m. from Friday to Saturday. This gives you plenty of time to chat up some cougars!

The best Milwaukee cougar bars in the suburbs

Travel just outside of city center and you'll find these fun bars that mature women frequent.

Regano’s Roman Coin offers entertainment and food choices and not just hot cougars

Regano’s Roman Coin exterior


Regano's is a well-loved urban bar in the heart of Milwaukee. With cheap beers, a diverse crowd and friendly staff, it's no wonder that this is also a cougar favorite. Young men also love hanging out here because of the affordable craft beer choices.

If you want to meet cougars who are smart, competitive and fun, Regano’s Roman Coin also provides some entertainment on any given night. Try building a cozy connection with an attractive older woman over a game of big buck hunter, pinball or pool. There’s also trivia night on Wednesdays and the occasional live music acts and sports games on the TVs, too.

Brisco County Wood Grill is where you go for good food and beautiful women

After a tiring work week, cougars in Milwaukee often retreat to their favorite restaurants and eat their favorite comfort food. The perfect place to do that is Brisco County Wood. It’s a restaurant with a country-western theme that serves great sandwiches, burgers, steaks, salads and ribs. The servings are huge enough for sharing and the prices are pretty reasonable.

The place is painted in dark, rich colors and adorned with all things western. But it’s spacious and inviting. You will fit right in and meet a lot of friendly cougars here. It also has a great bar area where you can order from their excellent draft beer selections. It’s great for big groups, but it won’t make you feel lonely when you're eating by yourself, too.

Cougars usually go here on Fridays and Saturdays. But you can also see Milwaukee cougars having lunch here during the week.

Snap a few fun photos in the Brisco County jail cell located inside the restaurant for a few laughs. Offer to take a photo for one of the ladies who want an Instagram post and you’ve got your perfect conversation starter!

Feel right at home when you hang out at Libby Montana Bar & Grill

This bar and grill has one of the biggest indoor sand volleyball facilities in the city. But Milwaukee cougars don’t just come here to play. They flock here because of the big food portions, too.

Libby Montana is very generous with its offers and promotions any day of the week. Happy hours are also extended up to 7 p.m. on Friday nights, which bodes well for the typical woman burned out by work. Play pool or darts and impress that cougar sipping her beer. Watch the game live and engage her in conversation.

If you’re visiting for the first time, try the Big Sky Burger, which is a juicy burger with Wisconsin cheddar cheese curds. It’s a real crowd pleaser! You can also sample the French dip sandwich or Javiar’s Firecrackers.

Libby Montana offers some really good options for food and drinks. Not to mention cougars who know how to have a good time and down beers in record time. It’s perfect for chilling with friends and meeting new friends. Beers are reasonably priced, and there’s even Sunday brunch from 11 a.m. to 2 p.m.

Where to pick up Milwaukee cougars at night

Feel like partying and dancing all night with older women? These clubs can help you out!

Gorgeous women flock to the dance floor at Site 1A

Beautiful single women seeking men on a night out at Site1A


If you love to bust a move on the dancefloor, then you need to check out Site 1A. You can find this awesome nightclub in the heart of Milwaukee's Historic Third Ward warehouse district. This is a place that you have to check out if you can appreciate a fantastic sound system with an incredible line-up of DJ acts.

Did we also mention that the women that come here are incredibly hot? Thanks to the DJ lineups, the women that head to this place are ready to party and let loose. So don’t be afraid to dance, even if you’re not the greatest. We promise, after a drink or two it won’t matter. The crowd here is super chill and welcoming. You won’t feel judged at all for going wild at Site 1A.

Mad Planet attracts some of the hottest women in our city

A live performance at Mad Planet


Are you looking for extremely hot older women with an eclectic taste in music? Then you need to check out Mad Planet. This is a veteran alt-rock dance club in our city. The club is known for hosting local bands along with a retro night complete with live DJs. Combine that with the great atmosphere of the place and what’s not to like?

Mad Planet has one of the most inviting dance floors in the city. It’s where your moves don’t matter as much as your attitude. We’ve met lots of interested cougars in Milwaukee while having fun on Mad Planet’s dance floor. So grab a drink by the bar and you’ll be blown away by both the music and the women who come here.

Where to meet older women in Milwaukee during the day

Fall in love with a mature woman during the day at some of our favorite daytime cougar hangouts.

Brunch with some sexy older ladies at Café Hollander

Slow brunch at Café Hollander


Located on Downer Avenue, people flock to this cafe because of its excellent brunch options. It’s usually packed on Sunday mornings with families. But you can also see single older women enjoying their meals with friends.

It’s nice to sit out on the patio on warm days. Inside, you can enjoy the friendly atmosphere as well. But this does not mean that all you will meet here are wholesome cougars. They can have a bit of naughty fun, too. Maybe after a few glasses of Belgian beers.

If the live acoustic music doesn’t put you in a good mood, then the Belgian beers surely will. They are an absolute must-try, and you can have them any day, any weather. Order the Jalapeno Burger to seal the deal and fuel you in your search for the chillest cougar this side of Milwaukee.

Why go to bars when you can be at Mad Rooster Cafe?

Good coffee from Mad Rooster Cafe


Milwaukee cougars love to brunch, and you can usually find them here at Mad Rooster Cafe. It’s a farmhouse-themed restaurant that’s always loud, bustling and crowded. But this is what makes it a great place to eat and hang out with family and friends.

The atmosphere is fun and vibrant. It’s got that cozy and homey vibe that folks love. But because so many people love this place, you need to book in advance if you don’t want to wait for hours just to get in.

It’s hard to pick what to order because of so many options, but you can never go wrong with the omelets and crepes. The French toast is a must-try, too. Don’t worry, though. Portions may be big, but they’re reasonably priced. So if you're in the mood for a big and filling breakfast, bring that appetite over here and meet an equally hungry cougar.

Lots of older women take classes at Daync Studio

An attractive couple in a dance class as Daync Studio


Are you tired of sitting out of going to clubs because you feel like you don’t have the moves? Then it may be time to take a dance class at Daync Studio. Daync Studio offers a variety of dance lessons for all levels. At Daync Studio you can learn how to dance salsa, bachata, hip-hop and contemporary.

Dance classes are also a great way to get to know new people in a short span of time. Everyone in the class is learning a new skill while mingling and having fun. Since you’ll be swapping partners, you can expect to meet a ton of beautiful and interesting women. So kill two birds with one stone by learning how to dance while flirting with lots of pretty women. You’ll wonder why you never took a dance class before.

My Cheeky Date is an easy way to meet lots of single women quickly

Meeting during a My Cheeky Date speed dating event


If you’ve exhausted all other options and want a quick and easy way to pick someone up, we recommend speed dating. It’s almost impossible to go wrong while you’re on a speed date. My Cheeky Date makes it even easier with their virtual speed dating events. The events are split up into age groups, which helps you meet someone within your own age.

My Cheeky Date makes sure to screen all of the men and women before setting up an event. Their speed dating events make it easy to determine if you instantly click with someone. After all, who wants to give up their entire evening to go on a date that might wind up being a disaster. So sign up to My Cheeky Date and see what kind of connections you can make!

Hate noisy bars? Try the unique drinks at Rochambo Coffee and Tea House

Woman drinking coffee at Rochambo Coffee and Tea House 


Where do cougars come to sip tea or enjoy a cup of coffee? They come to Rochambo on 1317 E Brady Street. This cute and charming tea shop attracts cougars who love a little caffeine in their system.

If you spot a cougar here, ask her if she has tried the Mystic Mocha--a combination of salted caramel, vanilla bean and magic. Anyone who tries it always comes back for more. Milwaukee cougars also love the alcoholic coffee beverages and the big tea selections. Did you know that you can ask the barista to put vodka in your tea?

You’ll see cougars sitting by their lonesome while reading a book or working on their laptops. As soon as they take a break, make eye contact and say hi. There’s plenty of room to chill with friends or relax by yourself. Check the area upstairs where more cougars can be hiding out. In case you’re wondering about the music, they play a lot of Asian instrumentals and jazz.

Keep in mind that drinks can be pricey, probably because they use all-natural ingredients. Come if you're looking for unique, tasty concoctions and beautiful coffee-loving cougars in Milwaukee.

Other great options for meeting cougars in Milwaukee

Need more places where you'll find single older women? We've got you!

Meet older women who love the classics at Bay View Books and Music

Outside of Bay View Books and Music


If you’re skipping the cougar bars in Milwaukee to find a certain kind of cougar, you should definitely drop by at Bay View Books and Music on Kinnickinnic Avenue. It’s the perfect place to while away the time as you go through different titles and dig through record crates. If you've read through some of our tips for finding local cougars you know that spending time in places the women you're interested go is absolutely crucial, especially when you share the interest.

Here’s where you can find cougars who love vintage books and records. Looking for an extremely hard to find record better be your idea of fun! Outside, the shop is quaint and unassuming. But don’t be so quick to dismiss the place as there can be cougars inside with great taste in books and music. It’s clean, organized and charming enough. Plus it has a large collection that will impress even the most discriminating collectors.

Not a lot of guys can appreciate the old book smell or the yellowing jackets of old vinyl records. But some cougars can’t get enough of it. Start educating yourself on the classics if you want to have a meaningful conversation with that beautiful cougar browsing through the shelves.

The top Milwaukee cougar dating app is eHarmony if you want a long-term relationship (try it now)

eharmony.com homepageIf you’ve been dating for a while and you haven’t found “the one” yet, it’s probably because you’re looking for love in all the wrong places. This is particularly true if you’re looking for women ages 35+. Older women tend to lead hectic lives between things like work, travel, and socializing with friends.

If you’re going out to bars and nightclubs to meet these women, you’re not likely to have very much luck because they’re either not there, or they’re there just to unwind with friends and have no interest in trying to meet men. These women are way more likely to look for men online because it saves them a lot of valuable time and headaches. So, which site are they using?

We won’t speak in absolutes since there are billions of women in the world and thousands of dating sites, but we can tell you eHarmony is the site that most guys are going to have the best results with (we certainly did). If it’s a quality woman you want who’s ready for a real relationship, no other site compares.

We have yet to find another site that gets results nearly as good as eHarmony for an average guy when you ONLY want a long-term thing!

They even guide the entire communication process in a great way. So if you’re a shy guy who struggles to talk to women, this can really help you get past the nervousness and get comfortable with your matches before you even meet. That really increases your chances of success.

There’s also a proven trial for new users which makes signing up and trying it out the easiest decision you make today. You really have no excuse to keep holding yourself back from meeting your dream woman. But don’t just take us by our word, try it out for yourself so you can see what you’re talking about.  Give them a shot and start getting the results you want.

Make your way to Mo’s A Place For Steaks

A nice steak from Mo's


Decor-wise, there’s nothing outstanding at Mo’s--just your usual steak house with a full bar on one side. But there’s no shortage of hungry mature women here who just want their steak cravings satisfied.

Aside from the beautiful cougars that frequent this place, you’ll also rave about Mo’s filet mignon, lobster bisque and Chilean sea bass. If you’re looking for a refreshing drink that will not make you heady right away, try the pear-based martini.

Mo’s has an upscale ambiance that does not temper down the warm neighborhood vibe. It’s a great place to get your tummy full and your interest piqued by all the cougars wining and dining there.

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

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