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The Expert’s Guide to Meeting Cougars in Milwaukee in 2024 - Where To Go And How To Date Them

A Milwaukee cougar out in town

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.

The Best Places to Find Cougars in Milwaukee 

Some of our readers may not be interested in diving through a long, 5k-word post just to decide where they're going to spend the night. We totally understand. That's why we chose to start with a short list of our favorite venues and dating apps that we know to be packed with single Milwaukee cougars.

If you're busy or in town for just a few days, then all you need is to hit these venues or use the apps, and the fun is guaranteed.

Here they are:

Young Milwaukee cougars with drinks at The Outsider Rooftop and Bar


The Outsider is a swanky rooftop bar with lots of classy Milwaukee cougars

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 at a dive bar. From there it’s all about positioning yourself for the perfect icebreaker with a gorgeous woman.


Homepage for AFF

AFF is the best way to meet cougars for bedroom fun (try it free)

It’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? AFF (which has a great free trial).

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 AFF 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 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.


Home page of eHarmony

eHarmony is by far, the best Milwaukee cougar dating site for relationships (try it free)

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 eHarmony's 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 eHarmony 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 eHarmony, most women using it are 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.

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 eHarmony 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.

eHarmony trial

If you haven't tried out eHarmony's 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 eHarmony is a recipe for success!

A Milwaukee cougar celebrating the new year at Victor's Nightclub


Gorgeous Milwaukee cougars flock to the dance floor at Victor's

If you love to bust a move on the dancefloor, then you need to check out Victor's. You can find this awesome nightclub in the heart of Milwaukee's Historic Van Buren street. 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 cougars that come here are incredibly hot? Thanks to the DJ lineups, the women that head to this place is 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.

A beautiful Milwaukee cougar on a date at The Outsider Rooftop and Bar


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

Top Milwaukee Cougar Bars and Cougar Clubs

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:

We added a bunch of cool cougar-friendly venues to the list above. Make sure you check them out. We also tried to make sure that every place we mentioned has plenty of beautiful single cougars.

So the next time you feel like meeting sexy Milwaukee cougars who want a romantic date or something a little more naughty, you know where to go!

A young Milwaukee cougar hanging out at The Outsider Rooftop


Meet Cougars in Milwaukee During the Day

Too much partying can be expensive, tiring and emotionally draining, especially for introverts. You meet so many people in one night it feels like you want to disconnect for a year. But parties/bars are where cougar hang, correct?


A cougar, or any woman, spends most of her week at work or in gyms, malls, cafes and grocery stores. It's almost an 80/20 ratio, and it's good because you get to talk to so many women in these places without wasting time, energy or money on clubbing. Also, the competition from men in these places is almost non-existent. Most men don't have the guts to say hi to a hot woman they don't know. But you will.

Where in Milwaukee? At these spots:

Milwaukee cougars sitting by the bar at The Outsider Rooftop and Bar


The Guide to Cougar Dating in Milwaukee

Now that we showed you where to meet them, it's time to tell you how and where to date single Milwaukee cougars. Women of all ages have some pretty universal dating preferences, so teasing and seducing a cougar won't differ much from hooking up with sorority girls, except for two things:

Cougars can tell if you're fake or not: They're experienced and have been with a fair share of men, so they can tell if you have your S together or just faking it. Sometimes they might play along if they don't have other options. But if they do, they will shut you down unless you come off as confident, playful and calm.

Cougars are specific: Unlike younger girls who write "Don't know yet" on their Bumble profile, a single cougar knows what she wants from the next guy, be it a fling, a ring or someone to help with the kids. Your success with her will depend on how you understand and match her preferences.

That's why the first date matters because it sets the tone for what's coming next. Here's how:

If you just want to keep it casual take her to a lounge

If your plan is to get her to bed as fast as possible - and she seems cool with it - then begin with a cool bar or lounge. The venue should be cool so you can share a few good moments, spark attraction and build comfort with her. It should also be close to your place so inviting her over will seem to make sense to her.

Below are some of the best romantic lounges and bars for dating cougars in Milwaukee:

If you're more serious about dating her, try a fun activity

I still recommend bars as your main option. However, sometimes it's better to build comfort with a cougar first before getting intimate especially if you're looking for something long-term or if she can't spend the night with you for any reason - like kids for instance.

These are a few fun activities to do with cougars in Milwaukee:

  • Bonkerz Comedy Club - 1721 W Canal St
  • ComedySportz - 420 S 1st St
  • Mitchell Park - 524 S Layton Blvd
  • Landmark Lanes - 2220 N Farwell Ave
  • Milwaukee's lakefront - 1701 N Lincoln Memorial Dr
  • JB's On 41 - 4040 S 27th St
  • Up-Down MKE - 615 E Brady St

I don't like chewing food while talking to someone I barely know, so I'm not a fan of restaurant dates. However, they're still good options for shy people who want to take it slow or those who prefer casual conversations without too much booze.

If the only option you have is a restaurant date, then take your Milwaukee cougar to any of these upscale restaurants:

A Map of All the Best Cougar Dating Spots in Milwaukee

To make bar crawling much easier, we combined our top spots for dating and meeting cougars in Milwaukee in just one handy map. Use it well, and don't forget to mention us with the good news.

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

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