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10 Places to Find Single Cougars in Connecticut You Can't Miss In 2023

Beautiful Cougars in Connecticut

It can be difficult to know where to find cougars in Connecticut, being that it’s a smaller state. You don’t want to waste time looking in the wrong places. Even if you’ve been living in the Constitution State for quite some time, we understand that there’s still a challenge in finding the finest Connecticut cougars. This is why we’re here to help you. We’ll give you tips and tricks on how you’ll maneuver your way into this state’s dating scene.

For starters, a change of place can be the change of pace you need in your cougar hunt. It all depends on where you are. If you’re in the Stamford area, try visiting Belltown. It’s the best of both urban and rural worlds. They have so many fantastic events happening that are perfect for socializing with the older ladies. Or if you’re in Hartford, the best way to go will be Downtown.

You should also try going to shopping malls and organic stores like Nature’s Way Health Foods. These places are perfect for some cougar watching. But if you really want to see them in action, flexing their muscles and perfect abs, you should go to gyms and yoga studios like Yoga for Everybody. You don’t really have to travel far and wide. You just have to use our tips to meet beautiful older women.

But wait, there’s more. We’re committed to helping you make your way to a cougar’s heart. So, where are the best spots to visit to find Connecticut cougars? Check out our list below and get your search on the right track today!

Destinations to Find Cougars in Connecticut

Here are some of our top-rated places to find sexy older women in Connecticut.

Enjoy a bustling night at Pizzeria Molto

Pizzeria Molto bar area


If you’re in Fairfield, you have to try Pizzeria Molto. It’s a hip spot with great food. From the appetizers to the pizzas and pasta, it really is a great Italian dining place. The prices are very reasonable too, considering you’re in the heart of downtown Fairfield.

It gives off an upscale vibe without feeling old and stuffy. The marble bar is where Connecticut cougars hang out. So check it out and strike up a conversation with the older ladies. Don’t forget to amp up the charm.

This place is very popular, so it can get crowded. It’s hard to get a seat at this place once the crowd comes in. In fact, you might even have to wait for one to two hours to get seated. Thankfully, there’s outdoor seating, so you can also enjoy the city lights and bustling streets. Or you can drop by on a weeknight or earlier on a weekend and hopefully you’ll meet a cougar to share a fantastic meal with.

For something short-term or casual you can’t beat AFF in our state

Homepage for AFF

When it comes to meeting cougars in our state, you have a ton of options. But if you want to meet a cougar who only wants a short-term fling, there’s only one site that we recommend.

If you haven’t tried AFF (which has a great free trial) before, you’re missing out on a lot of sexy opportunities. It’s a site that focuses on helping singles (and sometimes couples) meet other people for some fun. This straightforward site doesn’t exactly cater to people who want a long-term relationship. So if you only want to land a hot cougar in bed for a night or two and nothing more, try out AFF.

In case you’re wondering about the odds of meeting some mature ladies on the site, worry no more. AFF has a huge user base of women over 35 who are looking for some action. Each time we use the site, we only see a handful of younger women here. Sounds like a good deal if you prefer older women!

Try out AFF to meet some Connecticut cougars who will make your bed rock!

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.


Book yourself at Library Wine Bar & Bistro and meet cougars in Connecticut

A strawberry cocktail from the Library Wine Bar


If you’re a lover of books and libraries, you have to try Library Wine Bar and Bistro. It’s originally Wallingford’s town library, which was built in 1899. It serves some of the best Mediterranean and Portuguese food in New Haven county. Go here for brunch or some great booze at the bar at night. They have lots of Connecticut cougars whatever time of day you choose, so it all depends on you.

If your stilling wondering how it is guys meet a lot of cougars, it's places like this that make it happen.

This place also has a piano in the lobby, so they’re pretty swanky. If you want to listen to some great classical music, you can do so here. They’ve combined the essence of historic downtown Wallingford with the exotic cuisines of Portugal and the Mediterranean. This combination, together with its exquisite wine selection, brings you one of the most interesting dining experiences you’ll ever have. Chat up older ladies at this place. Then show them how well-read and exciting you are, and we’re sure you can bring one home.

eHarmony makes meeting a cougar for a relationship easier than anywhere else (try it now)

eharmony.com homepage

When you’re single and dating, the biggest challenge can be simply figuring out where all the single cougars are hiding. You know, like where do you even begin, especially when there are so many places to go and literally thousands of dating apps to choose from?

And what about for those of you looking for attractive older women with busy lives and demanding careers, because it seems to you like they’re nowhere to be found? In our experience, eHarmony is the best place to find single Connecticut cougars. They have over 30 million active members and a lot of single women over 35 (more than we have seen anywhere else).

Not to mention they are specifically responsible for 75% of all marriages that start online. No other site comes close to results like that!

On eHarmony, the signup process is more involved than it is on some of the other popular apps. It’s totally worth it because member profiles are much more in-depth, so you’re not relying on just a few photos when searching for matches. The process is really unique, and it means you’re matching with women that you’re actually compatible with, and not just making selections based on a pretty picture.

The women on eHarmony tend to be a lot more serious about finding real relationships when they’re signing up. There are very few women who are just looking for attention, which leaves you with a lot of options that are motivated to take action. Getting matches, messages and dates really are much easier on eHarmony than the other sites in our review of the top cougar sites, especially for guys looking for a relationship.

We haven’t found another site where guys who didn’t have great results elsewhere did nearly as well as they do on eHarmony.

eHarmony also offers a proven trial, so you can try them out first without any risk or obligation. This way, you get to see how well the site works at creating ideal matches when you’re out there dating lots of really great women. If you’ve been hesitant about online dating, this is the perfect opportunity to try out a site that’s been successfully matching up singles for nearly twenty years. Don’t miss out any longer. Create your profile here and start finding what you’re looking for today.

eHarmony trial

Reach The Olive Bar and be filled with hope

A crowd full of cougars in Connecticut at Olive Bar


Olive Bar is a melting pot of different people, which is why cougars in Connecticut love this place. They go here to check out the diverse crowd, hoping to catch the eye of young cubs like you. If you’re around the Unionville area, you have to visit this place.

The bar is actually attached to a Greek restaurant and pizza joint called George’s, but Olive bar has its own appeal. They have a distinct feel, so you know you’re in a different joint already. The decor is modern and the place is clean. You’ll also enjoy the cozy, dim, relaxed environment, which is often complemented with live music. Plus, they offer a wide variety of drinks and beer options to satisfy everyone’s preferences.

Word of warning: This place is usually packed, so we recommend you get here earlier to secure a good seat. Sit close to the bar since this is where the older ladies hang out. The bar area is also a great spot to catch a game since it features several huge TVs.

Watch the game and the older gals at The Elbow Room

Salmon teriyaki from The Elbow Room


If you like sports and want to meet a cougar who does as well, the Elbow Room should be one of your first stops. This dive bar has friendly bartenders, which is a blessing because single cougars in Connecticut prefer places where they can talk to the bartender and not sit in silence. Older women you find here tend to be easygoing and a lot of fun. Just be chill and casual in your approach, and you’ll surely charm the older women.

Cougar dating promo

Enjoy the tapas and the cougar selection at Rooftop 120

Beautiful older women at Rooftop 120


If you find yourself looking for a place to visit on a summer night, check out Rooftop 120. This classy bar is a great place to meet cougars in Glastonbury.

The vibe is definitely more upscale. And when the weather is good, you can go up to the rooftop to do some people-watching. The best nights to visit are Wednesday, Friday and Saturday. But be aware: you need to dress up to fit in here. You don’t want to go here looking like you just got out of a garage sale. You’re not going to attract any sexy older ladies if you do.

Apps Dating Coaches Actually Recommend To Meet Cougars in Connecticut

Can’t decide between going out to meet cougars and swiping through options online? Let us make the choice easier! Try out one of these dating apps that are super popular with cougars and you’ll see just how many of them you can get to know in one evening!

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

Head to Temple Grill in New Haven for great food and drinks

The dining area of Temple grill


If you’re looking for the kind of place where you can meet Connecticut cougars, look no further than Temple Grill. This place is a well-known hotspot among cougars, and they’re always looking for younger guys to keep them company. The bar is fully stocked. You won’t run out of drink options. Plus, you don’t need to dress up to impress the sexy older women who hang out here.

The best nights to visit are Monday, Tuesday and Sunday. Make sure you get there early enough to snag a seat. Otherwise, you’ll be standing all night!

Stop by Center Street Social for some sophisticated cougar fun

Sandwiches from Center Street Social


Sometimes you want a casual drink in a more upscale atmosphere. If that sounds like your kind of night, Center Street Social is a must-visit. This Shelton bar is a favorite location of fancy older women who are ready to draw in young cubs’ attention. It’s the perfect blend of classy and laid-back, with the best nights to visit being Thursday, Friday and Saturday. Make sure to visit this place during those times to get the most out of the experience.

H apps promo

Take in some live music while you flirt at The Acoustic

People watching a live performance at The Acoustic


If you’re a fan of the live music scene, definitely check out Bridgeport’s The Acoustic. This place is a great option to check out new, original bands. Better yet, it’s also an awesome place to meet artsy older ladies. The vibe is definitely more of a trendy, stylish hangout.

They have lots of up-and-coming bands and artists in attendance every night. Best of all, Connecticut cougars are known to prowl here. So if you want something a little out of the ordinary, The Acoustic is a great bet.

Have a classy evening at L’Escale with cougars in Connecticut

A classy woman on a date at L'Escale


While some bars are great for cougar hunting, sometimes you want a more sophisticated older woman. If you’re on the prowl for classy Connecticut cougars, L’Escale is the place for you. This Greenwich establishment is right on the marina. Plus, it’s a well-known hotspot for cougars who want a ritzier rendezvous with younger guys.

Not only do they have a full bar, but the food options are excellent as well. You do have to dress up to blend in properly here, so make sure you’ve got on your favorite garments. Once you do, you’ll surely catch the eyes of every cougar in the room.

H apps promo

Wine and Dine at Barcelona Wine Bar with Connecticut cougars

A wild party at Barcelona Wine Bar


It’s a pretty well-known fact that cougars prefer more exotic locales to meet younger guys. The average bar or nightclub probably won’t cut it with them. They need something a little more with flair. So if you want to meet the discerning cougars, you should go to Barcelona Wine Bar. It has branches in Fairfield, New Haven, Norwalk, Stamford and West Hartford.

This place has great food, a huge selection of wines, and a very romantic atmosphere. Those things are perfect for an intimate conversation with the sexy older woman you’ve been looking for. Weekend nights are the best times to go and make sure you get a seat at the bar. It’s perfect for people-watching, great food, and great conversation with cougars.

For more guides to meeting single cougars check these out:

Meet cougars in Colorado- Meet cougars in Delaware


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