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The Expert's Guide to Meeting Cougars in Portland in 2024 - Where to Go And How to Date Them

A Portland cougar at an outdoor cafe

Knowing where to meet cougars in Portland can take quite a bit of time without the right guidance! The city offers many great activities and spots where glamorous, older women hang out.

No matter what type of cougar you’re into, you’d likely find her here. You just have to know where to look. You can stroll the nearby Oxbow or Blue Lake Parks or the centrally located Mount Tabor Park to meet older women who love the outdoors. Or if you’re more into trendy women, you can hit up the Vault Martini Bar to attract a 30- or 40-something crowd.

Portland attracts various types of people. It also has many gathering sites that facilitate friendly (or flirty, if you will) interaction with single, mature women. All that’s left for you is to get out there and start talking to Portland cougars.

The Best Places to Find Cougars in Portland

We'll start this guide with a shortlist of the top apps and venues for meeting cougars in Portland. We know that some of our readers don't have time/patience for reading through a long, 5k-word guide.

We feel for you

That's why we made this short bundle for the impatient among you. Check it out, and make the best out of it.

Portland cougars having fun at Jackknife Lounge


Jackknife is a happening cougar bar in Portland

Established in 1995, Jackknife is an upscale bar located at 614 SW 11th Avenue. This is one of our recommended spots for Portland cougar spotting. When it comes to cougar bars in Portland, this trendy hot spot attracts a lot of older women who like Pan-Asian and Pacific Island cuisine.

The New York Times even recognized this bar for its exquisite tastes and atmosphere. Given that this is a classy lounge, young guys should dress their best if they’re looking to draw in that attractive cougar. And if you’re looking to enjoy good music over great eats, drop by on a Friday or Saturday evening when there are guest DJs.

Single woman

Homepage of AFF

Use AFF if you want to meet cougars just want something casual or physical (try it free)

Not every guy wants to jump immediately into a relationship. There are a lot of men who just want to have some fun with a Portland cougar and leave it at that. Unfortunately, typical apps are pretty bad at helping you find women who want the same thing. There are really only a couple of options worth try, but AFF (which has a great free trial) beats them all.

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 sex. The success rate combined with their free trial make it a pretty obvious choice to at least checkout.

When you want to get legit results and meet the most cougars for bedroom fun AFF is going to deliver for most guys.

The thing about other meetup sites is that they cater to a specific demographic. And on top of that, you’re not entirely sure if the women you meet on those sites want the same thing you do. On AFF, you won’t find any ambiguity. In fact, everyone on AFF wants sex.

Aside from being clear about what to expect on AFF, the site also has a slightly older crowd. Most users on AFF are aged 30 and above, which makes it the perfect hunting ground for some feisty Portland cougars.

Give AFF a shot, and you might just have an unforgettable evening with a gorgeous cougar!

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

For a real connection, eHarmony is our favorite way to meet cougars in Portland (try it free)

We love a good cougar bar as much as the next guy. But there are times when you just want to hang out at home while meeting hot older women. There are also a lot of Portland cougars who just don't spend any time in bars and clubs any longer. eHarmony (which has a great free trial) really helped us out.

While there may be a ton of apps out there, none of them are as good as eHarmony when it comes to helping you meet single cougars. We've spent a lot of time rating and ranking over 100 different cougar dating sites and apps and this is what we really like about it:

They just have the most Portland cougars using it

While their 33,000,000 plus membership doesn't make eHarmony the biggest site around, in our experience they have BY FAR the most real cougars using it. We're talking about attractive, single women over 35 who are interested in dating both younger and older men.

A huge number of women who use eHarmony are ACTUAL COUGARS. You won't find that anywhere else!

If you've tried to use more general dating sites in the past you know how hard it can be to find a real cougar. You have to sift through hundreds of profiles and MAYBE get lucky and find one.

The women are REALLY open to dating younger guys (and older guys)

A lot of women out there feel like there's a social stigma against dating younger guys. It's totally fine if a guy dates a younger woman but when a woman dates a younger guy it's different.

Because of this, a lot of women who are interested in dating younger guys don't advertise it, even on dating websites or when talking to younger guys in public.

With eHarmony, every woman is interested in guys of various ages. You 100% know that every woman you message wants to meet up with guys in your age range. It makes the process so much easier and more enjoyable.

It saves a ton of time and money

Spending any amount of time in a bar is expensive and you never know if any attractive cougars will even show up. If you want to make the most of your time and money a quality dating site or app is the best way to go.

You have to change your approach to change your results!

You shouldn't completely stop going out but being able to meet women 24/7 regardless of where you are is extremely powerful!

eHarmony trial

Do yourself a favor and give eHarmony's trial a shot here. It's easy to get set up and it is the best option for making a big improvement in your dating life that we've found. Try it!

Classy cougars in Portland having drinks at El Gaucho


El Gaucho is one of the best places to meet cougars in Portland

If budget is not a concern and you don’t mind paying extra for a sophisticated atmosphere then drop by El Gaucho. Learning how to meet and date cougars can be sped up a bit when you have money to burn. As you enter El Gaucho, you’ll be welcomed with shimmering candlelight, live flamenco guitar music, and a special dining experience. Don’t forget to make the extra effort to look dapper--sport your best dinner jacket and dress shirt.

El Gaucho is frequently visited by classy Portland cougars who are looking to mingle with debonair younger men. The place is also popular for its tasty steak and crab cocktail. Why not enjoy a plate of filet mignon while you’re at it?

El Gaucho also features a classy cigar lounge where you can share a fine cigar with a fine-looking older woman. Clink a glass of scotch to celebrate a night to remember.

Portland cougars on their way to party at El Gaucho


Top Portland Cougar Bars and Cougar Clubs

To help you get started, our team has put together a list of our favorite cougar hangouts. From restaurants to cougar bars in Portland, you’ll find them on this list. Here you’ll find the most attractive older women who are interested in dating younger men.

Here are the best places to meet single, mature women in Portland, Oregon:

We included a good mix of clubs, bars, and pubs in the above list that will make you happy. Just make sure you bring your best self to the venue.

Cougars have good eyes for details, so, dress well, and be calm, teasing, and slightly cocky. Old women are experienced and, if they're hot, they will tease you toe to toe till you either give up and walk away or prove you're worthy of being around them.

That's how it normally works.

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

A cougar in Portland celebrating ST. Patrick's Day with her friends at Kells Irish Restaurant & Pub


Meet Cougars in Portland During the Day

I'm a big favor for meeting cougars during the day. They spend more time shop, at the gym, walking their dogs, or getting coffee more than clubbing so it makes sense that you approach them where they hang out most.

These are the best places to meet single Portland cougars during the day:

Don't forget to warm up well before you go out. Talk to as many strangers as possible; cashiers, neighbors, baristas, old people..etc, the more the better. It's okay to feel nervous at first, it's natural.

Take it easy and focus on your state. What you say won't matter much as how you say it, so don't worry much about delivering the perfect opener, a "hi" will do if you say it with confidence and good eye contact.

Portland cougars hanging out at El Gaucho bar


The Guide to Cougar Dating in Portland

Dating cougars is a bit different from dating younger women who are often less experienced and only want to have fun.

Cougars, however, have been with a fair share of men and know what they want in and from a man. That's why taking them on a first date will depend on their blueprint and goals. Some will literally pick you up for a fun night while others will ask you straight away if you're serious or now.

We've seen it all. I was texting a cougar on Tinder a few weeks ago and it was going well. I teased her, didn't ask a lot of questions, and kept it playful between us..and then picked the right time to ask her out, and she said yes...on one condition...

Drum roll: She wanted a clear photo of my teeth because I wasn't smiling enough in my photos.

Some women are weird.

Anyway, taking a cougar out will differ from one woman to another. Here's how:

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

If it seems like she wants a quickie, then the plan is simple: Go to a nearby bar (or two), build enough comfort and sexual tension with her, and then invite her back.

Easy as easy can be.

But where to take her in the city?

Here are our favorite lounges to meet Portland cougars:

If you're more serious about dating her try a comedy club, piano bar, or fun activity

If she's not available for the night - kids maybe - or if she wants to know you first before sleeping with you, then why not share a cool, partially innocent activity with her? A comedy show, a piano bar, or even a hike...these things work too.

Here are a few cool experiences to share with a Portland cougar:

I don't recommend taking a cougar, or any woman, to a restaurant on the first date.


Because you won't be comfortable talking while chewing. However, some cougars are madly into fine dining. It gives them something to brag about among their friends and also helps them size up your wallet.

Anyway, if that's your woman's taste, then try hitting one of these cool restaurants in Portland:

A Map of All the Best Cougar Dating Spots in Portland

To make your life easier, we combined all our top venues for meeting and dating Portland cougars in just one map. Use it well and don't forget to email us your results.

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

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