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.
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.
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!
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!
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!
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.
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:
- Yamhill Pub - 223 SW Yamhill St
- Pub 181 - 18415 SE Division St, Gresham
- Candlelight - 7334 NE Glisan St
- Multnomah Whisky Library - 1124 SW Alder St
- CC Slaughters - 219 NW Davis St
- Sassy's - 927 SE Morrison St
- The Pilsner Room - 0309 SW Montgomery St
- White Owl - 1305 SE 8th Ave
- The Matador - 1438 NW 23rd Ave
- Portland City Grill - 111 SW 5th Ave 30th Floor
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.
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:
- Loprinzi's Gym - 2414 SE 41st Av
- Hollywood Fitness - 5223 NE Sandy Blvd
- Starbucks - 720 SW Broadway
- Good Coffee - 1150 SE 12th Ave
- Washington Square - 9585 SW Washington Square Rd
- Lloyd Center - 2201 Lloyd Center
- Vega Dance Lab - 1322 SE Water Ave
- YoYoYogi - 1306 NW Hoyt St #201
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.
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:
- Roof Deck at Revolution Hall - 1300 SE Stark St #110
- The Xport Rooftop Lounge - SW Jefferson St &, SW 2nd Ave
- Sapphire Hotel - 5008 SE Hawthorne Blvd
- Bar Casa Vale - 215 SE 9th Ave Suite 109
- Paley's Place Bistro & Bar - 1204 NW 21st Ave
- Tope - 15 NW 4th Ave
- Noble Rot - 1111 East Burnside Street
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:
- Helium Comedy Club - 1510 SE 9th Ave
- Curious Comedy Theater - 5225 NE Martin Luther King Jr Blvd
- Viking Gameroom - 1825 SW Broadway #36
- Portland Lawn Bowling Green - SE Bybee Blvd & SE 23rd Ave
- Portland Art Museum - 1219 SW Park Ave
- Multnomah Falls - Columbia River Gorge, Multnomah County
- Living Room Theaters - 341 SW 10th Ave
- Washington Park - 4033 SW Canyon Rd
If she's very old school you can always do a dinner date (but that isn't recommended)
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:
- Willow Restaurant - 2005 SE 11th Ave
- Mucca Osteria - 1022 SW Morrison St
- Jacqueline - 2039 SE Clinton St
- Le Pigeon - 738 E Burnside St
- Q Restaurant & Bar - 828 SW 2nd Ave
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: