How to Pick Up a Cougar – The Dos and Don’ts of Dating Older Women

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By Amber
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Want to date an older woman? Learn the dos and don’ts of How To Pick Up A Cougar today! Discover the secrets of successful cougar dating and make your night a roaring success.

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Are you attracted to mature ladies, and now you’re wondering how to hook up with an older woman? Well, look no further because I’ve got some tips to help you out.

As someone who’s been attracted to older women for as long as I can remember, I know firsthand that it can be intimidating to approach them. But with the right mindset and a little practice, you can be well on your way to dating the older woman of your dreams.

Whether you’re interested in casual hookups or something more serious, there are plenty of ways to meet mature gals looking for the same thing.

In this article, I’ll share some of the best tips and tricks for picking up a cougar.

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How to Meet Older Women? 8 Best Places to Pick Up a Cougar

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Before we dive into the best places to meet cougars, it’s important to understand what interests them. Older women typically have refined tastes and preferences, which can make it easier to find places where they hang out.

But now, let’s get you started on finding your silver-haired goddess. Here are the top spots to meet and connect with mature women.

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Coffee shops 

Coffee shops can be an ideal spot to meet older women. Many mature women love spending time enjoying a cup of coffee, reading a book, or catching up with friends over a casual drink. 

You can easily strike up a conversation by complimenting her taste in books, asking about her coffee order, or offering to share a table. Just be respectful and mindful of her personal space, and avoid coming on too strong too quickly.


Similar to coffee shops, bookstores can also be a great spot for picking up mature ladies. Many cougars enjoy spending time browsing the shelves for their next read. You can start a conversation by asking for book recommendations, sharing your favorite authors or genres, or offering to help her reach for a book on a high shelf. Yes, you think it’s cheesy, but hey, who said you don’t deserve a Hollywood-like romance? 

Yoga or fitness classes

Need a stretch? Join a yoga or fitness class to meet flexible, health-conscious older women. Most cougars have an active life and busy schedules, so they put a lot of effort into staying in top shape. 

You have several options here. Start a conversation before or after the class, or ask for her advice on a particular pose. Obviously, avoid interrupting her flow during the class.

Art galleries and museums

It would be totally weird to show up at these places just to find a date, but if you already enjoy checking out exhibits or strolling down history in a museum, maybe keep an extra eye out for who you may find there. 

Mature ladies are often into art and culture, so your local museum can double as your hunting playground. Show up dressed for the occasion, and if a lovely lady catches your eye, you can strike up a conversation about a piece of art.

Online dating sites


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Did you know that many online dating sites cater to older women and younger men? They are a great way to find and connect with mature women who are also looking for a younger partner. All you have to do is create a profile at some of the popular cougar-dedicated websites, which include:

These cougar dating sites often have advanced search filters that allow you to narrow down your search based on age, location, interests, and more, making it easier to find the right match.

Wine tastings

The cozy atmosphere and wide selection of wines make it a popular spot for mature women. Now, if you know a thing or two about wine, this will go much smoother. You can approach a lovely vixen and ask about her favorite wine to share a fun fact that will put a smile on her face. If you’re feeling confident, offer to buy her a glass and continue the conversation. 

Just remember not to come on too strong too quickly. Enjoy the company, sip on some fine wine, and who knows, you may just hit it off with that beautiful older woman you’ve been eyeing.

Volunteer events

Older women are often passionate about giving back to their community, so volunteering for a cause can be a great way to meet them. Choose an organization you’re passionate about and look for opportunities to volunteer in your local community. Not only will you be doing good for others, but you’ll also have the chance to meet like-minded mature women who are also making a positive difference.

Dance classes

Many older women enjoy dancing, and attending dance classes can be a fun way to meet them while getting some exercise. Sign up for a class and use the opportunity to introduce yourself, ask for tips, or compliment her moves. Not only will you have fun learning a new skill, but you may also meet a lovely woman who shares your interest in dance. 

Remember, though, that you are there to dance, so stay focused on the class, and let the connection happen naturally without pushing too hard.

And last but not least…

My Top Tips for Picking Up Cougars

dating a cougar

Now that you’ve learned about the places cougars usually gravitate to, it’s time to put that knowledge into practice. When you visit any of the spots mentioned above, use the following tips to test your skills in picking up cougars:

Be confident

If you’re looking to attract the attention of an older woman, confidence is key. Mature women tend to be attracted to men who exude self-assurance and are comfortable in their own skin. 

Show her that you know what you want in life and, most importantly, that you want her. Just be a gentleman about it because there is a fine line between confidence and cockiness. Remember, mature women, value authenticity and are attracted to men who are secure in themselves, not bigheaded brats.  

Dress to impress

Looks are not necessarily a deal-breaker, but they do matter when it comes to first impressions. Dress to impress and show her that you also care about your appearance. Go for classic styles that flatter your body and work with your personal style. In many ways, how you present yourself is a reflection of your confidence and sophistication, so put your best foot forward and make a great first impression.

Be a good listener

Obviously, you are after this gorgeous woman and want to show her you’re into her. Being a good listener and paying attention is a surefire way to score some points. Show her that you value her thoughts and opinions, ask questions, actively listen, and respond thoughtfully. By doing so, you’ll demonstrate that you’re not just a self-absorbed playboy but also care about her and what she has to say. 

Show off your sense of humor

Make her laugh and keep the conversation light-hearted. Use witty banter and playful teasing to keep things interesting, and don’t be afraid to let your personality shine through. Laughter is the best icebreaker, so use it to your advantage and make her feel good. Who knows, maybe you share a similar sense of humor which is always a plus!

Offer to buy her a drink

If you are still learning the ropes of how to pick up older women, offering to buy someone a drink can be a small gesture that goes a long way in showing your intentions and making a connection. It’s one of the oldest tricks in the book that will demonstrate your confidence. But if she rejects your offer, be a gentleman and walk away. No cougar likes a pushy, sore loser. 

Be upfront about your intentions

Honesty is always the best policy, especially when it comes to expressing your intentions to a mature woman. Let her know that you’re interested in her romantically, and be upfront about what you’re looking to get from this connection, even if your interests are purely physical. There’s no shame in that!

Be respectful

When you try to pick up mature ladies, always keep their comfort and boundaries in mind. Take your time to get to know your love interest. Many mature ladies have had unpleasant experiences dealing with younger men, so… take baby steps. Establishing trust and respect from the beginning can lead to a deeper and more meaningful relationship. 

Be yourself

Older women have been around the block, and they know when someone is genuine or just trying to score a quick fling. It’s absolutely fine to want to present yourself in the best light possible, but don’t try to be someone you’re not, as cougars appreciate authenticity.


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The Don’ts when Trying to Pick Up an Older Woman

How to Pick Up a Cougar - The Dos and Don’ts of Dating Older Women 1

If you’re interested in picking up a cougar, there are some important “Don’ts” that you’ll want to keep in mind. First and foremost, stop making assumptions about her based solely on her exterior. Just because she has a young spirit and looks better than a 30-year-old, it doesn’t mean she prefers casual sex and partying till the early AMs.

Always keep in mind that while some things might work on girls your age, they don’t often fly with more experienced vixens.

Here are some of the “Don’ts” when trying to pick up a cougar that will most certainly tank your efforts:

  1. Being intimidated: It’s natural to feel slightly intimidated when approaching a cougar, especially if she exudes confidence and assertiveness. However, remember that confidence is attractive, regardless of age –  and it goes both ways. So instead of letting your nerves get the best of you, try to project confidence and take the lead in the conversation or suggest a fun activity to do together.
  2. Talking about age: Talking about numbers can make her feel self-conscious or uncomfortable, and it can also make it seem like you’re only interested in her because you fetishize the fact she’s older than you. Instead, focus on building a connection that goes beyond age and superficial characteristics. And definitely keep clear of condescending comments like saying, “You’re cute” or “You look young for your age.” 
  3. Coming on too strong: Rushing into things when you are still learning how to pick up an older woman can be a major turn-off for most cougars. They do appreciate a “younger body,” but only if it comes with a more mature and sophisticated personality. After all, she wants to be your “woman,” not your “mom.” So, take things slow and allow the relationship to develop naturally, being sure to communicate your intentions clearly and honestly. 

Now, go get that cougar!

Dating a cougar can be an exciting and fulfilling experience if you follow the right approach.

By being confident, dressing well, being a good listener, showcasing your sense of humor, and respecting her boundaries, you can make a lasting impression on older women. Remember to be genuine and honest about your intentions while avoiding discussing age and coming on too strong.

Explore the top spots we’ve discussed for meeting mature women, like coffee shops, bookstores, dance classes, and online dating platforms.

With the right mindset and these essential dos and don’ts, you’re well on your way to finding and connecting with the older woman of your dreams. Now it’s time to take the plunge and put these tips to the test.

So, what are you waiting for? Go out there and charm your way into the heart of that silver-haired goddess you’ve been dreaming of, and don’t forget to enjoy the journey!

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Hello, I am Amber! I started cheating on my husband about 3 years ago. Not because I don’t love him anymore, but because he was away a lot and I got very bored. Now that I have a lot of background in the infidelity field, I thought it would be a great idea to share my experiences and tips. I know affairs have a terrible reputation, but in many cases, they can help to save a marriage! So don’t feel guilty, you too have the right to enjoy life and feel happy!