14 Great Bars and Places To Find Single Cougars In San Jose For 2020

Meet classy cougars in San Jose California at these spots

San Jose may be the third-largest city in California, but crucially, it’s the center of Silicon Valley, the world’s tech mecca. Practically everyone you’ll meet is involved in tech one way or another, whether they’re developers or part of a startup. Yes, this includes cougars in San Jose, making our city quite unique when it comes to dating!

Because of the fast-growing economy, San Jose is also one of the most expensive places in the US. The older women you’ll encounter here usually make good money and love intelligent conversation. But as much as they work hard, they also play hard.

From shopping at Santana Row to dropping by New Seasons Market for kale, cougars in San Jose know how to indulge themselves. They could also be clubbing the night away at in any of the bars downtown. After all, San Jose’s nightlife is wild. Swanky wine bars, sultry dive bars, live music venues, and hip and happening nightclubs are all here.

If you’re on the lookout for San Jose cougars, then our city has many excellent spots where you can find them. We’ve compiled a list of San Jose cougar bars and hangouts, so you can get a headstart on the dating scene.

Check out our list of proven spots below! We’d love to hear how it goes over at the comments section.

Where to Find Single Cougars in San Jose

Most ladies in San Jose are looking for the real thing rather than casual flings. But you’ll also catch some cougars who prefer to keep things casual! Here are the best venues to find them in San Jose:

Vino Vino is one of our favorite San Jose cougar bars


Wine and dine with some gorgeous women at Vino Vino

Vino Vino is just one of those San Jose cougar bars you need to visit if you’re a wine lover. If you’re looking to discover new wines and new mature women, then look no further! At Vino Vino, whether your knowledge of wine is limited or broad, you’ll never feel like an outsider.

With their great-tasting menus, you can easily discuss wine that you’ve just discovered with a beauty nearby. From there, you can talk to each other about the wines that both of you have tried. A smooth move would be to find out her favorite kind and then buy a bottle for the two of you. She’ll love the fact that you thoughtfully listened.

Vino Vino also has food, so if your drink goes well, then who knows! Maybe the two of you will be sharing dinner in no time.

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Adult FriendFinder is the best option out there if you just want all the fun without the strings attached (try it free)

Some cougars are out there looking for the love of their life. But other cougars have different plans. Some of them prefer to keep things casual, so they avoid relationships as much as possible. If that’s right up your alley, then there’s one site where you can meet like-minded cougars: Adult FriendFinder.

This site is perfect for anyone looking for some action and nothing more. The underlying agreement between all users here is that the site is for finding sex. No one’s on here looking for love. Instead, the users on Adult FriendFinder want one-night stands, quick flings and, in some cases, other kinky encounters that you’ll have to see to believe.

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

Over the years, we’ve tried Adult FriendFinder to find casual meetups. We’ve found that a large number of users are in their 30s or older. So for all you cougar hunters out there, you’re in luck! You’re sure to meet some horny single cougars on AFF.

Try Adult FriendFinder and meet the cougar who will rock your world!

Try AFF For Free


La Foret draws in classy cougars in San Jose


Find a delicious French dish at La Foret

La Foret is a lovely place to grab some mouthwatering food. With its extensive French menu, this restaurant offers you a glimpse into the Parisian culinary scene. It’s also a great place to meet that beautiful older woman you’ve been looking for.

If you see a woman sitting at the bar, then ask her what she’s planning to order tonight. It’s an easy way to strike up a conversation that’s relevant and flowing. From that, you can then see if she is someone you’re interested in getting to know more. Maybe ask her if you can get to know her better over a French 75.

This amazing place will have you excited about the food and the women. It’s ideal for spending time with the cougar that catches your interest!

Cougar Life has been our favorite way to meet cougars in San Jose (try it free)

Homepage for Cougar LifeWe 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 San Jose cougars who just don't spend any time in bars and clubs any longer. Cougar Life (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 Cougar Life 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 San Jose cougars using it

While their 7,000,000 plus membership doesn't make it 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.

Every single woman who uses Cougar Life is an ACTUAL COUGAR. 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 Cougar Life, 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 Cougar Life's free 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!

Try Cougar Life For Free


Wine and dine beautiful San Jose cougars at Vintage Wine Bar


Vintage Wine Bar for savoring drinks on an outdoor patio

Spending time with a gorgeous cougar doesn’t have to mean partying around for hours in nightclubs. Vintage Wine Bar has a quiet, intimate atmosphere, and you’re still likely to meet older ladies here.

After all, there’s a lot going for it. It’s set in the middle of Santana Row, a top shopping and dining destination with cougars everywhere. The atmosphere is also chic and classy, from ambient lights to a bamboo fountain.

Most of the seats are on the outdoor patio. It’s a delight, especially in the evening, because you’re overlooking Santana Row and can easily people-watch. Friendly conversation is a norm, and it’s natural to talk for hours here while enjoying a drink.

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Aside from offering cougars a break from all that shopping, Vintage Wine Bar has an amazing wine and whiskey selection. Even when you’re not too familiar with wine, the servers are always ready with recommendations. Alternatively, you can start talking to nearby cougars by asking them about their favorites. If they find you cute, they’ll definitely keep chatting with you!

Vintage doesn’t serve up huge meals, but their selection of cheese, chips and bread go well with the wine.

Homepage for EH

We see a lot of cougars around San Jose looking for long-term relationships on eHarmony (try it now)

Just like fashion or food, the dating scene has trends too. And if you want to keep your dating life alive, you gotta get with the times. San Jose cougars know this better than most (we're a tech capital yah know) and more and more their skipping the social scene in order to just meet guys online. We've found the eHarmony has been the most successful way to meet them, by far.

It works with your schedule no matter how crazy or unusual it may be. You can approach women much more confidently with a buffer in between. And you can meet dozens of women each day, many that you wouldn’t come across in your daily life. Now that online dating is such a mainstream thing, there are so many sites and apps to choose from. Good thing we tried over 100 of the top cougar dating sites to find the best, so you don’t have to.

eHarmony has a few things going for it that really stood out for us:

  • A ton of active users (over 30 million) and the most cougars of any site we tried
  • REALLY active women that were very responsive to our messages and dates
  • A system that actually did a great job of matching us up with women we were interested in (and were looking for guys like us)

When you have a lot of options with women who are looking for more than an ego boost you're going to get results. eHarmony's easy trial signup process did a great job of understanding what you're looking for and weeding out all the women who aren't really committed to meeting guys. That means that they end up doing a great job matching you up with compatible women who are VERY responsive. Getting this many responses for messages and dates is what online dating is supposed to be like.

We haven't found an easier way for guys to meet cougars looking ONLY for long-term relationshps than eHarmony!

They really do a lot to help out guys who haven't been super successful with women. If that sounds like you you're going to have your best results on eHarmony (in our opinion). It's easy to use, has a lot of receptive women, and it just plain works. We all know couples that met on eHarmony.

So if you’re getting sick of the same old dating scene like we were, check out their proven trial, switch things up and you’ll be amazed at the women you’ll meet.

Try eHarmony Free


Savor the outdoors with cougars in San Jose at McCormick's and Schmick's


Expand your tastes and meet a hot cougar at McCormick and Schmick’s

McCormick and Schmick’s is a seafood restaurant where the food is refined and the women are even better. If you’re looking for a fantastic meal and some great company, this will be the place to find it. It’s a classy place that offers a great dining experience as well some of the best drinks in San Jose. Sophistication oozes out of this place, and you’ll notice it in the clientele of women that eat here. So go grab yourself a delicious meal here! You might meet a mature beauty to share it with.

The Branham Lounge is one of the top cougar bars in San Jose


Keep it casual with a San Jose cougar at The Branham Lounge

This cozy cocktail lounge has San Jose cougars arriving in droves. Thanks to plenty of seats and a warm, intimate atmosphere, it’s easy to get to know your cougar better.

The Branham Lounge is a popular venue for groups of friends to blow off some steam after a day in the office. Cougars can drop by here for a few warm-up drinks before heading off to a nightclub.

Where else can you meet hot single cougars in San Jose but Santana Row?


Santana Row is excellent for cougar hunting

Santana Row is well-known in the city for being an excellent spot to pick up San Jose cougars. This bustling street is one of the most upscale in the area. It provides a wealth of shops, restaurants, cafes and bars to choose from.

During the day, you’ll find cougars walking through elegant boutiques. On the other hand, the wine bars and restaurants are the highlights at night. Cougars usually arrive in groups of two or three. They might be relaxing with some after-work drinks or settling down for a meal with friends.

Be sure to put extra effort into your appearance. By looking smart and confident, you’re sure to catch a cougar’s eye.

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Additional Great Cougar Bars in San Jose

Here are more cougar bars for flirting with alluring older women. Play it right, and you’ll end up with her number and plans for future dates:

Unwind with a down-to-earth San Jose cougar at Britannia Arms


Have an amazing night out with mature women at Britannia Arms

This lively pub is great for finding fun San Jose Cougars who want to party and have a great night out with you. There are live DJs on Thursday, Friday and Saturday nights. As for bagging a sporty older lady, you can turn to their weekly game nights.  Britannia Arms also features drink promos every day from 4 to 7 p.m. The ladies just love the regular karaoke and trivia nights!

The Britannia Arms has a vibrant, friendly atmosphere. Even on your first visit, you might already be knocking back drinks with an attractive, mature lady!

Why not have fun at a popular San Jose cougar bar like Dive Bar

Despite its name, Dive Bar is not one of the typical cougar bars in San Jose. Still, you can’t help but fall in love with its charm. With a fun atmosphere and eclectic drinks, how can you really go wrong?

When you meet your special lady, you can start a casual conversation about what brought her to Dive Bar. Afterward, invite her to shoot a game of pool or ask her if she wants a pint or a spirit. Either way, this is a great place to let your hair down and relax!

Share drinks with sophisticated San Jose cougars at Vbar

Vbar can be found in the cool Santana Row district. It’s one of the more upscale San Jose cougar bars, and attractive and elegant cougars love to come here on the prowl. The bar has seductive red lighting and edgy artwork adorning the walls. You’ll find plenty of comfortable leather armchairs and stools where you can enjoy an intimate conversation.

Flatscreen televisions and a state-of-the-art sound system provide plenty of entertainment. You’ll be happy to indulge in the extensive drinks menu. San Jose cougars love to hang out on the terrace or enjoy a meal in this chic cocktail lounge. Vbar is seen as THE place to be, so expect classy ladies who know what they want.

You won’t be short of competition for your cougar. Look sharp and up your game, and you’re on your way to a fantastic night.

Three Flames Restaurant for top-notch food and entertainment

Three Flames Restaurant and Banquets is the place to be if you want satisfying food and casual entertainment. You’ll find San Jose cougars here singing their heart out to karaoke or hanging out at the bar in search of eye candy.

Three Flames consists of both a bar and a restaurant, so it’s comfortable to stay around here all night. It’s been running strong for 30 years. The atmosphere is warm and friendly, and the crowd here is usually older.

The bar offers beer, wine and cocktails. Happy hour runs from 3 to 6 p.m. on weekdays. You can treat a gorgeous cougar to drinks and house wine for a bargain price of $4.50.

On the other hand, if you prefer a fun, rowdy setting, then drop by later at 9 p.m. Friday and Saturday are the peak days, and people will be dancing it out to DJ music. The rest of the week, karaoke is the main event.

Either way, there’s always the restaurant to move on to after drinks. Get to know a cougar better by sitting down with her and indulging in the signature New York Pepper steak. It could be your first of many dinners together!

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Hedley Club is the place for live music among San Jose cougar bars

Hedley Club is a cozy wine and cocktail bar and a great option when you're tired of dating out of town and are exclusively looking to find a cougar locally. San Jose cougars love going here for a sophisticated yet laidback evening out, and many are on the prowl for young guys. As you’d expect from a hotel bar, Hedley is decked out in plush art deco style, complete with velvet couches, booths, wooden chandeliers and soft lighting.

What makes it even more magical is the live music. Fridays and Saturdays are the best time to go because of the jazz performances from 8:30 to 11 PM. There are also bands playing from Wednesday to Sunday. On the quieter days, it’s easy to chat and unwind with the tasteful background music.

Drinks are a little bit on the pricey side, ranging from $5 to $19, but you’ll be getting your money’s worth because of the magical ambience and free live music. Their drinks include seasonal cocktail specials and high-quality wine. Combine these with an appetizer plate or a full-blown pizza for you and your cougar, and you’re set for a great impromptu date.

Dance the night away at Blue Pheasant

If you prefer a more low-key cougar hunting ground, then the Blue Pheasant may be exactly what you are looking for. This restaurant is classy and old-school with a welcoming atmosphere. Everyone who steps through its doors feels right at home!

The cuisine here is good-quality American fare with fresh ingredients from local suppliers. Their wild fish, burgers and steaks are all pleasant, and they have a good drinks menu too.

Cougars in San Jose appreciate the chic yet casual ambience. In fact, you’ll often notice groups of older ladies enjoying a meal and wine at this pleasant eatery.

As night falls and the drinks flow, why not move on to the lounge and nightclub? It’s your chance to get on the dance floor and impress the ladies.

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

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