14 Portland MILF Hot Spots You Need To Check Out In 2020

A beautiful woman in a beanie hanging out in town

Do you have a taste for the attention of beautiful single moms? Are you on the prowl for the perfect Portland MILF? Well, as you probably know it isn't always easy to find them.

Meeting people in Portland is usually no problem for tourists and locals alike. The folks here are pretty friendly after all. But you need more than just friendliness and luck if you want to meet some lovely Portland MILFs. You need a guide.

Other guides out there might suggest typical places like Paley’s or Higgins. But you don’t want to go there lest you encounter plenty of rivals for a hot mama’s attention. Instead, we’ll give you some slightly lesser-known spots where MILFs in Portland are known to hang out.

Take a look at our list and see just how many MILF hotspots there are in the City of Roses!

Where You Can Meet a Portland MILF

Here are some places in Portland that you have to check out if you want to meet some beautiful single moms!

Strike gold at The Old Gold

The beautiful bartender at The Old Gold

drinkinoregon.com

The Old Gold has been called one of Portland's Best Whiskey Bars by Thrillist. Its offerings include the best of the best from Tennessee, Ireland, Scotland and Japan. Don't forget about the bourbon and rye options either, which includes Angel's Envy and Whistle Pig. Pair your drinks with beer-battered French fries, tofu bánh mì or an elk burger.

This classy spot also hosts weekly events such as tap takeovers, DJ parties, themed trivia nights, and whiskey classes, which give you more opportunities to meet more MILFs. It’s little gems like these that you should be aware of when out to meet MILFs in your city. Whatever your deal is, you’ll definitely find an Old Gold event that will strike your fancy.

Pro tip: dress up before heading here. While it’s no crime to drop by in casual clothes, you’ll up your chances with the hot mamas if you’re in a crisp shirt.

Adult FriendFinder is where we meet the most MILFs who just want a guy to sleep with (try it free)

Homepage for Adult FriendFinderWe have had a lot of fun trying out all the popular apps for meeting MILFs in Portland. Most were a complete waste of time (though fun to try) because there just aren't many apps or sites that get the attention of women 30+.

It’s hard NOT to recommend that guys at least check out Adult FriendFinder (you can try them for free with the links above after all). We have seen a lot of guys find success using it. And most of those guys have been pretty average in the looks department. With that kind of success and how little time it takes to use there really isn’t a downside.

To be completely straightforward, it’s the only app we found that has a lot of Portland MILFs who were interested in meeting up. Everything else (including Tinder) just couldn't compare to Adult FriendFinder. That's why it's always one of our all-time best hoop sites list.

There isn't an easier option out there for most guys to meet single MILFs who want to skip the commitments and get to the fun!

We had the best success with AFF and think you will too. If you are tired of spending time and bars and clubs or talking to women for hours only to find out they have a boyfriend you should try Adult FriendFinder. It only takes a few minutes to sign-up and it could change your dating life completely.

Try Adult FriendFinder For Free!
We've tried out a lot of different sites and apps to meet MILFs and nothing has worked nearly as well as this site. You need to check out Adult FriendFinder's free trial with this link if you're serious about meeting women and want to stop wasting time. There isn't a faster or easier way to meet MILFs that actually want to meet up and head to the bedroom that we've found.

 

Fire things up with a Portland MILF at The Fireside

The Fireside in the afternoon

pdxfireside.com

The Fireside is "a neighborhood joint" that opens up early and stays up late. Whether you’re in the mood for Sunday brunch or to let off some steam on a Friday or weekend night, the Fireside is the best place to be.

Owners Wendy Hessel, Sue Erickson and Dick Singer wanted a place that was comforting and a food menu that was inspired by the outdoors. And that's exactly what they've created.

Enjoy an Out-n-Back and herb-roasted chicken by the fire or a Sauvie Island Afternoon and summer pasta on the outdoor patio. The Fireside provides a friendly, neighborhood atmosphere that makes it easy to get to know the other people, MILFs in particular. Watch things heat up with a Portland MILF as the fire burns.

Using Cougar Life has been the most effective way for us to meet cougars in Portland (try it free)

Cougar Life homepageLike many of you, we don't have a ton of time and money to spend going out all the time trying to meet Portland MILFs. Between work, school, and other demands on our time we're lucky if we can get out a couple of nights a week! This is where Cougar Life has made our life a lot easier (and why you should check out their free trial).

MILFs have the same problems! They have been skipping the usual bars and clubs more and more and ONLY meeting guys online. Modern men need to use all the technology at their disposal to get the best results!

If you're not looking online you're going to be missing out on a LOT of great opportunities!

We've tested, ranked, and reviewed all the legit sites out there for meeting MILFs and there are a few main reasons why Cougar Life really stands out:

Cougar Life has the most Portland MILFs using it

When you're comparing different dating sites and apps the first thing you have to look at is the numbers. Just how many MILFs are actually using it? Without a lot of single women actively looking for guys you're going to be wasting your time.

Cougar Life has over 7 million active users and EVERY SINGLE WOMAN on the app is a single MILF or more mature woman. 

You simply can't find that ANYWHERE else. It does a great job of attracting a very particular type of woman and making them feel comfortable enough to stick around. No other option comes close.

These women aren't here to play around

The vast majority of women on Cougar Life are there to get down to business (in a good way). They want to meet guys and they don't want to waste anyone's time doing it.

If you've tried other dating sites and apps you've probably noticed that most of the women are just looking for attention and compliments. They don't REALLY want to meet up with any guys, they just want their daily self-esteem boost. Cougar Life is the opposite. Women are using it to actually get results. If they wanted validation they would use the larger free apps to get it.

Younger guys looking for MILFs won't do better anywhere else

Older guys looking to date MILFs can do pretty well in most places, including Cougar Life. Younger guys have a much harder time. You never know if a woman is open to dating younger guys or how she'll react when you approach her.

Cougar Life is the only option out there where you 100% know that every woman is interested in dating younger AND older guys!

When you know the women you're messaging are very interested in guys your age it changes the game. You can be way more confident and that means you're going to be way more successful.

If you haven't checked out Cougar Life's free trial you need to. It's really easy to get set up and it can really change your dating life. You need to try something new if you want to get new results and this is a great way to do it!

Bring out your inner crooner at Trio Club

DJs playing dance music for the crowd at Trio Club

triokaraoke.com

Trio Club is a +21 nightclub, restaurant and bar with a swanky Las Vegas vibe. It’s perfect for letting loose and connecting with other club guests. Plus, it has a karaoke lounge, so you can impress the MILF of your dreams by belting it out.

They have food available to go alongside a beer or cocktail. The Trio Club has two separate dance rooms: one playing current hits and the other playing Latin music. It’s the closest thing to a Vegas night club you can find in Portland, Oregon. Don’t forget to drop by on a Wednesday to avail of Trio Club’s free couple and line dance lessons at 7:30 p.m. You might just need a partner to do that. But finding one in this club shouldn’t be so hard.

Meeting MILFs in Portland for long-term relationships on eHarmony is where we solid success (try it now)

eharmony.com homepageMeeting Portland MILFs seems to be getting harder with each passing year. It's not hard to see them hustling along during the day but after 5 p.m. there just doesn't seem to be a lot of them in the usual social spots. So, where are they all hiding?

Women who are a little bit older have busy lives. So they’re not usually out in places like bars or nightclubs. And if they are, it’s more likely that they’re unwinding with friends after a long day. They’re usually not just sitting around waiting for guys. Instead, a huge number of them in a progressive city like Portland now exclusively meet guys online, especially on eHarmony (where we saw the best success).

Busy people want to cut to the chase and use a site that does a lot of the work for them. eHarmony is the best dating site we’ve found for this. The signup process for the proven trial is a little more lengthy in comparison to other dating sites. But this is actually a good thing because it makes their matching process significantly more effective.

By taking the time to thoroughly fill out your eHarmony profile, your personality will shine through. You’ll then match only with women you’re actually compatible with and based on your criteria. It also weeds out all the women who aren't really serious about dating or just want attention.

You'll find a responsive and engaged group of women than on eHarmony! Our response rates for long-term relationships were great.

With a member base of over 33 million and a reputation for being a site responsible for 75% of marriages that start online, it’s no wonder eHarmony is so popular with MILFs in Portland. It works, and it’s always on our list of the best sites for meeting single moms.

They even have a proven trial so you can get started right away. Do yourself a favor and sign up. It's the best option out there for most guys, especially those who aren't incredible at attracting women.

Happy hour at Brix Tavern brings in all the MILFs in Portland

Beautiful MILFs in Portland at a get together in Brix Tavern

@BrixTavern

Brix Tavern is famous for its many hours of happy hours. And in that we mean they have early and late happy hours all through the week. With that in mind, you will be happy to know that MILFs often frequent Brix, for good food, a good selection of beers and a good offering of fun.

Drop by for an early dinner with some friends. Hang out for a bit as you see the MILFs pouring in from a long day at work. After all, this is one of the most popular places to find single women seeking men in Portland. Some come here just to unwind, but a lot of them go to Brix to have a little fun with the guys.

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Go cocktail crazy at Teardrop Lounge

The classy circular bar of Teardrop Lounge

teardroplounge.com

Sit your sexy self down at the curved island bar at Teardrop Lounge in downtown Portland. If you live in the area, this is a proven location for finding a lot of local MILFs. Many Portland MILFs frequent this sensuous cocktail heaven. They come for the drinks, but they stay for the company, making this one of the many Portland hookup havens.

Order a lovely foxy lady a unique and creative cocktail from the experienced barman. Then watch as the conversation flows along with the follow-up drinks.

Portland City Grill has a view to die for

Friends enjoying some wine at Portland City Grill

@PortlandCityGrill

The view alone will get the tongues a-wagging, a great talking piece for sure. Portland City Grill is sophistication over a glass of wine and a warm fire. Whether it’s a good steak, a tasty seafood dish or just a really awesome blend of wine you are looking for, book a table and get ready to meet up with Portland’s finest mature women.

Now the question is, would it be easier to meet MILFs at Portland City Grill than it is to meet them through our compilation of the best dating sites in Portland? We'll let you decide!

Goodfoot – good food – good company

The 60s inspired sign of Goodfoot

@goodfootlounge

Portland MILFs love Goodfoot. With an awesome range of music from the 70s to the current tunes, you will find all ages at Goodfoot. So choose your night carefully and take a little trip down to suss out the players. But don’t get despondent if you land up there on game night.

Goodfoot has a few pool tables and some old fashioned pinball machines. Many single moms also love to sneak a game between drinks. So don’t be shy; give her helping hand as she tries to pot the blue in the top right pocket.

Beyondages.com video course

Doug Fir Lounge is a luscious spot with live bands

The rustic Doug Fir Lounge

@dougfirlounge

Doug Fir Lounge pulls in the women without question, from the young and reckless to the older and more cultivated. With their connection with Red Bull, Doug Fir Lounge converted their original green room into the now much-adored red room. Be sure to check this old relic out as well as take a load off in the lounge area while you're in the company of classy cougars in Portland.

Portland MILFs love a little bit of music and a sweet cocktail. So make a turn at the Doug Fir Lounge for a fun night out.

Get a taste of local flair at Portland's Farmer’s Market

A few people buying goods at Portland Farmer’s Market

@portlandfarmersmarket

The MILFs of Portland don’t only frequent the bars and restaurants. They also like the outdoors as well and a Farmers Market is the best place to find a single mom who cares about her health. From music to food events, from a dining series to a variety of different market venues, grab a basket, get all healthy-like and go find yourself a Portland MILF with a love of nature.

Monthly Art Walks in Portland attract plenty of MILFs

Lots of people shopping for art at the Monthly Art Walks

travelportland.com

Happening every first and last Thursdays of the month, as well as the first Fridays, these monthly art walks draw in people from all over the city. The artsy mommies love a good art festival and this has an art vibe like no other. So check out all the artworks from local and visiting artists. Then grab a drink and meet a pretty lady who appreciates art. You might even run into artsy and single BBW in Portland! So wouldn’t it be romantic to have your first date amid the art installations all around?

You need to try this

Rialto Pool Room is an Oregon original you can’t miss

A beautiful mature woman playing pool at Rialto Pool Room

@RialtoPoolroom

Rialto is just plain old-fashioned fun. With pool tables, a couple of authentic bars and the best-distilled spirits and cocktails to die for, you have to make a turn. Even Playboy names Rialto’s Jack London one of the best in America. In fact, if you meet someone from our list of the best dating apps in Portland, you could also go to Rialto for your first date!

So, what are you waiting for? A yummy mummy is expecting you down at Rialto’s, pool queue in hand and a smile to boot.

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