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The 13 Ideal Places to Find Hot Wisconsin Cougars In 2023

Attractive Wisconsin Cougars

With so many options around, it can be difficult to know where to find cougars in Wisconsin. You’re in the Dairy State, and you don’t want to get milked out of money by wasting your time!

So why not try a change of scenery? If head to the Madison area, try visiting Hawk’s Landing. This neighborhood is lush with Wisconsin cougars. Or if you’re in Milwaukee, try Historic Third Ward. You’ll fall in love with the old brick buildings and the exciting nightlife. But if you want to do a bit of cougar watching, shopping malls and organic stores like Whole Foods will be your best bet. Then, you can go all the way and join them in their yoga sessions. Older ladies love to get fit both in mind and body.

So where exactly are the best places to find cougars in Wisconsin? Check our list below and read on for our list of recommendations!

Where the Wisconsin Cougars Hang Out

Here are some of our top selections where you can find a sexy older woman:

Visit Le Tigre Lounge to meet feisty cougars in Wisconsin

The quirky bar at Le Tigre Lounge


If you are in Madison and looking for a unique find, this is the place to be for great drinks and a great environment. It’s an unusual yet iconic place where you can enjoy some local ambiance. It has the oldest liquor license in Madison, which makes it an interesting spot. It also has a throwback lounge atmosphere that is truly something to see and enjoy.

As the name suggests, most of the decor here are tigers. They even have a live tiger-cam from a rescue facility in Florida for your viewing enjoyment. But if you’re here for a different type of wild cat, you’ll find them here too. The cougars in Wisconsin love Le Tigre because it gives them a nice balance of rich history and a fun time. Don’t miss this place if you want to meet these ladies!

For relationships between the sheets, AFF is all you need

Homepage for AFF

If friends with benefits and one-night encounters are your thing, the dating world can be tough to navigate. You might meet hundreds of attractive women who want to go on a date with you. But the minute you mention that you want something casual, they’ll bolt. Now you’re left with no dates and the feeling that women just aren’t willing to sleep with you.

Let AFF change your perspective. On this site, you’ll meet hundreds of women who just want to get laid. They don’t want romantic candle-lit dates or wholesome weekend getaways. The women you’ll meet here are looking to get down and dirty, and they’re not afraid to say so!

Even if you’re only looking for a certain breed of Wisconsin cougar, you’ll have great odds of meeting them here. Most of the women who use the site are at least in their 30s, so you won’t have to wade through profiles of ladies who are too young for your liking.

Let AFF cure your dry spell with a huge user base of horny singles. Create an account today and you could be sliding between the sheets with a hot cougar tonight!

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 AFF'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.


Have a good time at Camp Bar Tosa

Friends having fun at Camp Bar


What will amaze you most at the Camp Bar Tosa is the variety of ages and personalities. On a typical weekend night, you’re bound to see everyone from college kids to middle-aged Wisconsin cougars. There’s a good reason why everyone is there, though, and it’s the setup and atmosphere. The place is perfect.

The bar itself definitely resembles the typical neighborhood bar with a few TVs and a retro feel. But aside from that, it’s unique in almost every other way. If you get bored with just socializing and having drinks, you can play darts with your lady. There are so many things you can do in this place, and you’re guaranteed to have fun.

eHarmony is by far the best place to meet older women who want a relationship (try it here)

eharmony.com homepage

While you may meet a lot of wild cougars in Wisconsin, there are also plenty of them out there who want a serious relationship. The problem lies in knowing where to look. These cougars don’t usually frequent bars and nightclubs because Wisconsin’s nightlife scene is more for people who want something casual. So instead of simply hanging out at random spots hoping to meet a single cougar, why not take your search online?

Of all the apps and sites we’ve tried for meeting older women, the one that takes the cake is eHarmony. It’s not your regular dating site. Instead, it’s exclusively for singles who want to find a serious relationship. But don’t worry, it’s not a site where you simply match up with singles based on a few photos. eHarmony actually does the work for you.

When you create your account, eHarmony will have you fill in a survey about your personality and your preferences. The site then works double duty to help you find compatible singles in their user base. After a day, you’ll get a list of eligible Wisconsin cougars who fit your preferences. It’s easier than hanging out at yet another bar.

For guys who are a little shy, eHarmony also helps facilitate conversations between you and the ladies you’re compatible with.

This helps avoid awkward first dates and misunderstandings about your expectations. All in all, we always enjoy meeting older women on eHarmony. So try out their great trial for yourself and see just how many cougars in Wisconsin you match up with. Who knows, you might end up in a relationship sooner than you thought!

Drink wine with Wisconsin cougars at Vintage 38

The Instagram-worthy bar at Vintage 38


If you’re a lover of all things vintage and sophisticated, try Vintage 38. It’s a spacious establishment with a wide variety of wine selections and about 12 rotating craft beers on tap. If ever you’re in Greendale, this place is a must-try.

The artsy decor and intimate space create an amazing atmosphere. They have wines from all over the place, which adds to the worldly feel of the bar. And in case you don’t know what to order, the staff is more than happy to assist you.

Try their sparkling rosé. It’s an absolute cougar favorite. If you happen to spot an older lady who is your type, buy her a glass and start flirting from the get-go. The bar also has a bookshelf of games and books to complement your drinks. So if conversations aren’t your strong suit, a quick game over drinks might get you lucky.

Stop by Mo’s for a great steak with cougars in Wisconsin

Lots of cougars in Wisconsin frequent Mo's Irish Pub


Located in downtown Milwaukee, Mo’s is a lively bar and restaurant with a diverse crowd. It also has delicious food and a full bar. Plus, you’ll meet some of the finest older ladies in the city.

Wisconsin cougars love this place because of the trendy atmosphere. But they also love that you don’t have to dress in your Sunday best to fit in.

Mo’s is a unique blend of an upscale establishment with a relaxed atmosphere. This makes it one of the most versatile places on this list. You can stop by and look for an older lady that strikes your fancy. So if you’re looking for a good meal and the company of an older woman, look no further than Mo’s.

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Mingle with Wisconsin cougars sipping on tasty cocktails at Elsa’s On The Park

The entrance to Elsa's on the Park


Well-known for its great cocktail menu and upscale atmosphere, Elsa’s On The Park is a must-try. It’s one of Milwaukee’s most popular places to grab a drink. This East Town hotspot is famous for its drinks and the surprisingly good food options. Overall, it’s a great place to meet cougars in Wisconsin.

It’s an upscale venue with a little more class than the average bar. This attracts sexy older women looking for younger guys. And because it hardly ever gets overly crowded or noisy, you can have meaningful conversations with the Wisconsin cougars you’ll meet. The best time to visit Elsa’s is late at night. Be sure to plan your moves accordingly. Don’t come off too strong and be calm and friendly in your approach.

Apps Dating Coaches Actually Recommend To Meet Cougars in Wisconsin

Can’t decide between going out to meet cougars and swiping through options online? Let us make the choice easier! Try out one of these dating apps that are super popular with cougars and you’ll see just how many of them you can get to know in one evening!

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

Dance the night away at Hody Bar & Grill with Wisconsin cougars

Patrons of Hody Bar and Grill having drinks in winter


This Middleton staple is a great place to check out live bands. Do a little dancing and meet the Wisconsin cougar you’ve been looking for. You don’t need to worry about dressing up here because the atmosphere is super casual.

Hody also has a great selection of craft and specialty beers. So, if you consider yourself a beer connoisseur, you’ll find a lot of new favorites on tap. If you do get lucky with one of the many Wisconsin cougars that come by, don’t worry. You’re just a short walk away from the Staybridge Suites, where you can continue your evening in private.

Course promo

Make it a wine night with Eno Vino

Burgers from Eno Vino Wine Bar


If there’s one thing that cougars love, it’s a great wine bar. So, if you’re in the Madison area, you’ll definitely want to take a trip to Eno Vino. This wine bar and bistro is the perfect location for meeting a sexy older woman. It’s got an upscale (but not stuffy) vibe and an extensive wine list.

So whether you’re just popping in for a quick drink or making an evening out of it, Eno Vino has everything you could want.

Visit Cleo’s Brown Beam Tavern for signature cocktails

Lovely ladies on a night out at Cleo's Brown Beam Tavern


Do you love Christmas and wish you could celebrate it year-round? Are you looking for a bar that’s filled with beautiful cougars? If so, we have just the place for you: Cleo’s Brown Beam Tavern.

Not only is this Appleton hotspot an excellent place to meet cougars, but it’s also a great place to make new friends. The patrons are friendly (must be that Christmas spirit). Plus, the signature cocktails are delicious, making it a perfect spot for an evening on the town. The best nights to drop by are Tuesday, Wednesday and Thursday.

Single woman

Get your culture fix at the Museum of Wisconsin Art

The spacious exhibit area of the Museum of Wisconsin Art


You might think an art museum is an odd place to try and meet women. But you have to trust us: it’s a much better bet than you realize. The great thing about art museums is that you don’t have to compete with a bunch of guys vying for the same woman.

Even better, art museums are filled with conversation starters. All you need to do is ask a Wisconsin cougar’s opinion of the art piece on the wall. Then, you’re all set. See where it leads and enjoy the company of a cultured cougar.

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