15 Great Bars and Spots To Meet Single Cougars in Milwaukee in 2019

A couple of attractive cougars in MilwaukeeAre you looking for cougars in Milwaukee, Wisconsin? You will love Milwaukee’s dating scene for older women as it has become very liberated the past few years.

Single, middle-aged women in the city freely go out with younger men and there are also lots of establishments and cougar bars to find a potential date. 

Don’t forget that finding these women is only half the battle. If you really want to improve your ability to attract and date them once you meet you absolutely have to check out our incredible video series with our proven step-by-step approach to meeting and attracting cougars over 30.

You will not find an easier or better solution to improving your ability to attract cougars anywhere.

Don’t waste your time with lower quality spots and check out our favorites below.

Places To Meet Cougars In Milwaukee

Here are the best places you should check out if you’re on the lookout for cougars in Milwaukee:

Victor’s Cocktail Lounge & Restaurant  is a cougar favorite 

Every weekend, cougars in Milwaukee come out in droves to this establishment.  The reasons vary. Some go here because they can’t get enough of the food like the fish fry and prime rib.

Others love that the DJs play 80s and 90s music. The reasons really don’t matter; what’s important is that you can find a lot of attractive, older women in this restaurant.

You can always find cougars in Milwaukee on Cougar Life

If you want to maximize your chances of meeting a single lady in Milwaukee you must be online.

A large number of women here are ONLY looking online these days, especially for younger guys.

These are women with lives and careers so they don’t have a lot of time to spend taking in the Milwaukee nightlife.

We have reviewed, ranked, and compared all of the top dating sites for cougars and Cougar Life has been the best around for years.

Sometimes, you don’t have to go out to meet a middle-aged woman. You only need a computer or mobile device with an Internet connection.

If you value your time you should be spending at least part of it on Cougar Life (you can try it for free with this special offer)

You really have nothing to lose and there is a lot of potential for gain.

Leave her a message or if she’s online, chat with her right away.

Karma Bar & Grill offers longer happy hour

Yes, this is a sports bar which is mostly frequented by men. There are lots of TV screens showing different sports. So why would you go here to find a cougar for a date?

Well, aside from being conveniently located at 600E Ogden Avenue in downtown Milwaukee, this bar and grill also has its happy hour up to 7 in the evening.

It is a little more generous when it comes to that aspect compared with its competitors.  Other cougars also enjoy the entertainment brought by stand up comedians.

Instead of having your eyes glued to a Packers game, why don’t you get a glass of beer and offer it to a lovely lady out there in the patio?

If you are looking for something short-term you need to try Adult FriendFinder

Cougar Life holds the crown for the best overall site for meeting cougars in the city. If you are not interested in an actual relationship and just want something short-term or one-time Adult FriendFinder is going to edge them out a bit (though they are still pretty good). They also have a free trial which makes it easy to try them out.

With over 50 million members and a long track record of delivering value to members (they have been around since 2006) there isn’t a better option out there. You might be thinking “what about Tinder” and that is a great question. The thing is that Tinder is only useful if you want to date women between 18 and 28. Once you start looking for cougars in their 30’s and 40’s Adult FriendFinder is way better.

Give their free trial a shot and check out your options around here. We have tested out all the proven hookup apps and they have been tops for a while. We have spent a lot of time trying out the Milwaukee hookup bars, hookup apps, and hookup sites that actually work so we know.

Lucille’s Piano Bar & Grill has the coolest live show

This establishment probably has the hippest live show in Milwaukee. Every night, piano players and a musician on the drums take song requests from the audience.

The performers come from all over the country. Moreover, the music is eclectic—from old 90s hits (think of the Spice Girls) to more contemporary artists like Taylor Smith.

Cougars in Milwaukee enjoy its very laid-back atmosphere. The diversity in music also appeals to them. Try to be here on Thursdays where there are lots of specials in store for patrons.

If there’s one thing you won’t be thrilled about this place, is that it has very steep prices. Hence be sure to come in here with your pockets full.

Otherwise, you could end up disappointed in your bid to date a cougar.

Whiskey Bar is busy almost all week long 

Whiskey Bar is one of those bars that are busy all through the week. There seems to be no off-peak hours in this bar.

Go here every Tuesday as the happy hour special runs for almost the entire night, meaning you’ll get discounts on beers and cocktails.

It’s also the time of the week when many middle-aged women can be seen in this bar.

Located in Cathedral Square, this bar is smack right in the heart of Milwaukee’s drinking scene. The building where it is located is easy to find.

Libby Montana Bar & Grill offers a lot of discounts

This bar and grill has one of the biggest indoor sand volleyball facilities in the city. But cougars don’t come here to play volleyball.

They flock this restaurant/bar because it is very generous, with discounts offered to patrons almost every night.

Happy hours are extended up to 7 in the evening on Friday nights, which bodes well for the typical middle-aged woman burned out by work.

Café Hollander serves excellent brunch

People flock here every weekend, especially Sunday morning, to have a serving of its excellent brunch. You might want to go there on a Sunday morning, but you will have to take a chance as you will likely see families instead of a hot, middle-aged woman.

Still, you can go here at night just to check what the fuss is all about. The beer selection is extensive and it helps that the prices are pretty affordable.

Port of Call Bistro & Beer Garden is pretty cool, too

Tacos, margaritas, and beer. These are three great reasons why a lot of people chill out at this bistro and beer garden.

Cougars in the area are often seen every weekend. Plus it offers a magnificent view of the garden and downtown Milwaukee.

Brisco County Wood has delicious and cheap food

After a tiring week, cougars in the city retreat to their favorite restaurants. One of them is Brisco County Wood.

It serves a wide variety of comfort food ranging from sandwiches, burgers, steaks, salads, and ribs. Moreover, the prices are pretty reasonable.

Cougars in the area are often spotted every Fridays and Saturdays. But you can also see a few middle-aged women eating here by themselves during lunch.

Why don’t you take a chance and start a conversation with someone who’s years older than you?

Seek Out These Hot Cougar Bars in Milwaukee

Find the hottest cougar bars in MilwaukeeHere are a few extra cougars bars to check out:

Envoy brings art deco design to cougar bars in Milwaukee 

Located in the Ambassador, Envoy is a fantastic addition to Milwaukee’s premier art deco hotel.

This bar specializes in classic American cuisine with an artisan twist presented in a relaxed yet sophisticated atmosphere.

Older women love this hotel bar for its delectable meals.

Entice a lovely lady by exchanging conversation over crab cakes benedict, huevos rancheros or homemade corned beef hash.

If you enjoy weekend dates, try picking up an older woman during Sunday brunch from 10am-3pm.

Victor’s Cocktail Lounge & Restaurant is your spot for food and sexy singles

Cougars love visiting Victor’s Cocktail Lounge & Restaurant on weekends for this bar’s fish fry and prime rib.

There are also many food specials across the week including homemade spaghetti & meatballs on Mondays.

Ladies also love the energy of the dance floor when DJs play 80s and 90s music as well as Top 40 hits.

Young guys can also create an intimate experience with an older woman while relaxing in their huge leather booths.

So be sure to drop by and pick up a cute older woman while enjoying a great drink together.

Elsa’s On The Park gives Milwaukee cougar bars the café-feel

Located at 833 N. Jefferson Street, this swanky bar and restaurant draws in many middle-aged women looking to unwind.

Elsa’s on the Park is well-liked for its chic and intimate Euro-café feel.

Ladies love the American and Italian inspired menu and delightful drink menu.

They especially enjoy that the kitchen is open until 1 am for the entire week.

Elsa’s also stretches cocktail service for an extra hour until 2am Sunday through Thursday, and until 2:30 on Friday and Saturday.

Just a note: if you visit after 5pm, all visitors must be 21 years of age and older.

Whiskey Bar is your cougar bar with a great whiskey selection 

Located in the heart of Milwaukee’s downtown, Whiskey Bar is perfect for young guys and older women who love the taste of a great glass of whiskey.

This venue is elegant, casual, professional, and festive.

Patrons love its fully stocked bar, transformable stage, large dance floor and its own audio, video and lighting equipment.

Tuesday is particularly popular because Happy Hour runs for almost the entire night.

Regano’s Roman Coin is your bar of choice for cougars and jukebox tunes

Regano’s is a much-loved urban bar in the heart of Milwaukee.

With cheap beer, a diverse crowd and friendly staff, it’s no wonder that this dive bar is a cougar favorite.

Young guys will love this spot because of its affordable prices and craft beer choices.

If you are also into women who enjoy fun on any given night, this venue also has a few points of entertainment.

Try building a cozy connection with a lovely older woman over a game of big buck hunter, pinball, or pool.

If you and your lady love to dance, there’s also an internet jukebox that you can play tunes on.

Bottom line is that this is an excellent location as far as cougar bars in Milwaukee to have great fun and meet a sexy single while you’re at it.

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