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How to Seduce an Older Woman Regardless of Your Age

Woman being seduced by a younger man

Honestly, you need to put some thought into how to seduce an older woman, since not a lot of older women are interested in dating a younger man. And even if you do spot a cougar, it can take more than your boyish charms to seduce her. So if you want to learn the top techniques you can use for seducing older women, read on!

My cougar seduction journey started at a busy nightclub. She was thirty-four, tall, blue-eyed and athletic--a beautiful woman. Although we had intense chemistry, I couldn’t have prepared for what she said only thirty minutes into our conversation.

She whispered into my ear, “Are you going to take me home or not?” and I was stunned. I’ve never had a woman proposition me so directly, let alone such an attractive one.

Sadly, I didn’t know it at the time, but I had just discovered one of the three keys to seducing an older woman. I’ll explain what happened next with her very soon.

But first, I want you to know something important.

Things To Know About How to Seduce an Older Woman

There are several key differences between younger and older women that we're going to cover.

If you understand these differences and how to use them to your advantage, seducing older women will become a satisfying process. One that’ll regularly lead you to experience things that would normally be reserved for a “Dear Penthouse” letter.

These are things you will need to know whether you're meeting older women online (try out some of these sites and apps we've had a lot of success with if you haven't) or as you normally would in person.

What might older women like in younger men?

On the surface, it might seem like younger men won’t have much to offer an older woman the way an established older gentleman would. After all, younger guys typically won't have the life experience or the spending power of someone closer to her age.

If you do have these attributes, that's fantastic. But if you don’t, it's not necessarily game over. You can make up for it by showing certain characteristics young guys usually have in abundance.

Plenty of older women are drawn to younger guys because of their natural zest for life, youthful energy, thirst for adventure and curiosity for new experiences. This includes their ability to not take themselves too seriously.

These are some of the attributes that can help older women feel young again. They're also some of the things older women consider before having sex with a younger man.

This attitude towards life is infectious and it feels great to be around. To some extent, we all retain a certain nostalgia for the excitement and carefree days of young adulthood.

So, if you’re thinking about how to seduce a mature woman, you could be the guy who makes her feel this way. If you can demonstrate this free spirit, spontaneity and adventurousness, party-all-night attitude, you'll capture the imagination of a lot of older women.

What's more, a lot of older women can't resist the innocent naivety of younger men. They like the idea of teaching younger men about life. So don't be afraid to show curiosity towards the parts of her lifestyle you know nothing about.

This certainly beats an older man who knows a lot but is bitter about women and how life has beaten him down.

The Hookup Apps Dating Coaches Recommend Most To Meet Older Women

Whether you're looking for your first hookup or are more experienced there are a few apps that tend to give regular guys the best results. These are the ones that our dating coaches have seen guys consistently have the best results with older women:

SiteOur ExperienceOur RatingFree Trial Link
Best Hookup Site For MILFs
Experience Highlights
Experience Highlights
  • The best way to meet MILFs for hookups by far
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
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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

What older women don't like in younger men--and how to avoid showing this

The main factor deterring older women from dating younger men is immaturity. Younger guys often lack the emotional maturity needed to look after a fully-grown woman. So you better believe she'll be screening to see whether you have this . . .

If you show signs of approach anxiety or general nervousness around her, she's likely to be less forgiving than many younger women.

If you're unable to display the assuredness needed to make her feel safe and comfortable in your presence, it'll be tough to win her over. After all, this is masculinity in a nutshell. It's a must-have for older women.

However, if you can make her feel comfortable while also showing the fun-loving energy of a vibrant young man, there's little else that's going to stop you. And more often than not, an older woman will fall for you hard, right on the spot.

That said, you should fully expect an older woman to give you a little grief if you clearly look younger than her. She'll need to test to see if you're grounded enough to handle her shit tests.

How will you react when she calls you a “little boy?” Will you become defensive and fall into her trap? Or will your confidence remain unwavering?

Perhaps you can give a cheeky smirk and make fun of her concerns. Maybe you can flip the script and assure her she doesn't seem too old to hang out with you. It might just take a chuckle, strong eye contact and the utterance of, "So what do you like about little boys?"

Whatever you do, she needs you to remain in your masculine frame of power in these moments. This is what it takes to be her man. This is what mature women respect in men, no matter the age.

New course

You need to be comfortable, so get some practice online first (our favorites)

You can get a lot of experience in meeting and attracting older women through various online dating sites. When it comes to women over 35, we have two sites that have worked the best for us:

If you want something long-term, try eHarmony first. They have the largest number of single older women (35 and up). They’ve also been around for a while, so you know they’re legit. Give their trial a shot and see what we mean.

If you just want sex, then AFF (which has a great free trial option) is our go-to. This site focuses almost exclusively on matching people for sex. So don't expect to find a normal relationship here (though it's possible). You can also try them for free so it’s worth checking them out to see the quality of women in your area (most cities are pretty good).

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.


Older women are more sophisticated

Older women have had enough life experience to be bored by guys who only talk about surface-level matters like pop-culture and sports. They crave more interesting and fulfilling conversations, something meaningful that’ll make them feel more alive.

So how to seduce an elderly woman if you’re a younger man? Well, if you can talk about things most guys never do, you’ll stand out as far more intriguing than the many boring guys she usually meets.

Recently, I met a beautiful Spanish woman at a bar. And in the two hours before we slept together, our conversation spanned topics including existentialism, how the death of our fathers affected us and our biggest fears.

Our conversation was emotional, vulnerable and meaningful. Because of this, she felt it was only natural to invite me to her place for some drinks in private. Your conversations with all women should have some depth to them, but especially your conversations with older women.

If you don’t know what to talk about, fret not. Any topic can spark a deep or meaningful conversation if you know how to approach it properly and spark interest. As long as you show genuine interest in the topics you’re both talking about and she eagerly continues the conversation herself, you’re good to go.

You see, when it comes to seducing older women, it’s not about learning pickup lines and routines. And it’s certainly not about learning the “right” thing to say. No, older women want you to be real with them, to show them what you’re made of, and to be present in the moment. That’s the key takeaway from this.

So, don’t be afraid to express yourself and your personality when you’re with an older woman. They’ll appreciate it greatly.

How to seduce an older woman by getting in touch with your emotions

When learning about how to get an older woman to sleep with you, you need to know why emotions matter and how to talk about them. That’s because women love to talk about feelings. But this is something most men just don’t get.

Talking about your emotions (and having her talk about hers) will make her feel a sense of connection and comfort with you. Besides that, emotions are the cornerstone of all attraction and affection. And people just can’t help themselves but feel at least a little bit emotional when talking about various emotions.

Just make sure not to only bring up positive emotions, but a full spectrum of emotions.

For example, many younger guys are intimidated by older women. Because of this, they’re hesitant to do anything that might be perceived as negative when interacting with an older woman.

They’re afraid to make her mad or uncomfortable. They’re afraid to “ruffle her feathers” and tease an older woman. And that’s not good because it stifles these guys and ruins their chances of success.

One way to show you’re not intimidated by an older woman is to clearly say if you dislike something she does or says. Don’t hesitate to let her know if you disagree.

This doesn’t mean you should become antagonistic and start seeking reasons to disagree with her just like that. You need to do it when you actually disagree with her and not force it. It’ll work wonders because being confident enough to disagree with her is actually quite attractive.

A classic example of this is the dynamic between Han Solo and Princess Leia in the original Star Wars trilogy. It shows you aren’t a wimp, which creates sexual tension.

Show her your vulnerable side

Create a deep conversation with an older woman by using the power of vulnerability. Contrary to popular belief, being vulnerable has nothing to do with being weak. It’s actually quite the opposite.

Being vulnerable is about being confident enough to talk about things that most people would keep hidden, especially from a woman they barely know.

Vulnerability shows a strong sense of self-worth. It also creates trust--both of which are key elements in seducing an older woman. You show you trust her by sharing some personal stuff. And she shows she trusts you by not going around and gossiping about it.

Some examples of vulnerable topics include:

  • Your hopes and fears;
  • Any memory that helped shape who you are;
  • Mistakes you’ve made;
  • And other things most people would only tell a close friend.

When bringing these topics up, the point isn’t to make her feel sorry for you. Instead, you want to share something about yourself that most people wouldn’t share because you believe she will get to know you better as a person. She’ll get to see what makes you tick, what your hopes and dreams are, and how you experience the world.

Being vulnerable yourself will lead the woman you’re interacting with to share similar thoughts about herself. This will lead the two of you to create a powerful connection and a sense of mutual trust.

As Brené Brown, an American professor and researcher and one of the foremost experts on vulnerability says, “Staying vulnerable is a risk we have to take if we want to experience connection.”

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Seducing Older Women Isn’t As Difficult As It May First Seem

There are so many reasons older women are dating younger men now. So now it’s time to reveal a couple of incredibly useful tips to make you even more irresistible to older women.

The first one is showing her you’re a passionate person. And the second one is showing her you’re a competent person. Both are incredibly important, so pay attention.

Seduce an older woman by showing her what you’re passionate about

Older women are used to older men who have mostly settled down and gotten comfortable in their way of life.

Unfortunately, these older men don’t have the same enthusiasm and fervor their younger counterparts do. That’s one of the reasons older women find youthful passion extremely attractive.

When interacting with an older woman, talk about your passions, your plans and your ambitions. Talk about the band you’re in, the business you want to start, and all the ways that you want to make an impact on the world.

Most importantly though, talk about your passions passionately!

Show her you’ve got a fire under your ass and that you have the energy and drive to go and achieve things. Show her you wake up every day with a glint in your eye and a desire to take on the world with your ideas.

Simply talking about your passions can be a boring experience as well. That’s why you have to actually show it, and not tell. By being more lively, emotional and energetic when you talk.

Also, when you talk about these things, make sure to talk about how they make you feel, as opposed to listing various statistics and facts about whatever it is you’re talking about.

If you do this right, she’ll find your youthful energy and enthusiasm incredibly seductive.

Older women expect a man to know what he’s doing

To be honest, when I first met that beautiful cougar, I found her quite intimidating. I was only twenty-one at the time and she was in her early thirties. Not only was she incredibly attractive and self-confident, but she was also quite successful. She makes well over six-figures as a high-level executive.

We had met a few hours earlier at a local club, and after a great conversation and some drinks, we ended up in her bedroom. As excited as I was, I couldn’t help but overthink. I was afraid this woman was out of my league and I would screw things up. That was my biggest mistake as it forced me to not be in the moment.

As we started making out, I hesitated to take off her clothes. She could sense my hesitation, and she blurted out, “Is this amateur hour or something?”

I was totally embarrassed . . . I had screwed it up. She ordered me a cab back home.

That night was embarrassing. But I also learned an invaluable lesson: older women expect a man to know what he’s doing. The fact that I had overthought and hesitated turned that woman off to the point she lost interest in sleeping with me.

If you hem and haw when seducing an older woman, it’s not going to end well. This is true throughout the interaction, but especially when it comes to sex.

If you’re that nervous around older women, at least fake it till you get used to it. Because one of the things older women respect the most is competence. So you better show her you know what you’re doing and that this isn’t your first rodeo.

How to overcome your anxiety about dating older women

If you’re not sure how to fake it till you make it when you’re figuring out how to seduce a mature woman, then this section is for you.

A lot of younger men may feel intimidated by this huge list of expectations that older women tend to place on romantic partners.

Indeed, if you don't have a lot of experience in life (or in the bedroom), you may feel anxious about even trying to make something happen.

However, the personal growth that comes with facing your fears and pursuing these relationships far outweighs the risk of looking silly.  Spending time with these women and learning from them will do so much to supercharge your development as a man.

It forces you to level up and transform into the type of man who could hold his own in a relationship with a “real woman.” This development will be incredibly attractive to women of all ages. It will help you push to success in many areas of life.

So, instead of running away from what intimidates you, dive in. As with any other fear, it becomes easier the more you face it.

Basically, feel the fear and anxiety and do it anyway. That’s the only way to real success.

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How To Ask An Older Woman To Sleep With You

There are two main points you need to consider when it comes to understanding how to ask an older woman to sleep with you.

You can either be very direct about it. Or you can simply take charge and lead your interactions to sex yourself.

I’ll explain everything below in more detail.

Be direct because older women don’t play games

After the thirty-four-year-old beauty asked me “Are you going to take me home or not?” she called an Uber and brought us straight to her place.

We got inside, and as she was walking towards her room she began taking off her clothes. First her jacket, then her shirt, and then her pants. As she stood by her bed, she undressed completely. She got on all fours on her bed before saying, “Well, what are you waiting for?”

That night was the first of many that taught me an important lesson: older women don’t play games.

They are much more comfortable with their sexuality than their younger counterparts. They’ve been around the block a few times. So they are more likely to want to have sex with a guy they just met.

It’s important you understand this as you learn how to seduce an older woman. Because if you try to play games with older women, it’ll usually backfire. They’ll wonder why you can’t just be real enough to go for what you want.

Obviously, this doesn’t mean you should just walk up to older women or message an older woman online and say, “Hey, wanna have sex?” It simply means if you find her attractive, be as direct as you can be.

Also, don’t hesitate to be physical. Be forward enough to kiss her, especially if you see signs that she wants you to kiss her. Older women appreciate a no B.S. approach. So if you usually like to be indirect and subtle, drop that when interacting with older women.

Don’t hesitate to invite her to your place, whether you met her online or in person. Older women want a guy who goes for what he wants. So there’s no reason to wait to take her home.

Learn to take charge if you want to seduce an older woman

Most younger women tend to have hang-ups about sex. So it can be useful to take your time and gradually escalate. With older women, this dynamic is very different, you want to be bold in the bedroom.

This doesn’t mean older women don’t like foreplay (far from it). But it does mean making out for half an hour before you attempt to take off her shirt is wholly unnecessary and even anti-seductive for her.

If you want to seduce an older woman, take charge. She knows what you want and she wants it too, so don’t make her wait. She’s not an immature girl--she’s a real adult.

In terms of performance, chances are it’s not your experience that’s going to impress her. It’s your vigor. When having sex with an older woman, take her the way only a younger man could, and you’ll have her begging for more.

If you're the type of guy with the stamina to bang like a pneumatic drill or go several rounds in one night, that's likely to score you several points. A great attitude is to confidently lead her in the bedroom, while also remaining open to being taught a few lessons. After all, she probably has a few tricks up her sleeve too.

If you’ve gotten this far, make the most of your new-found partner and let her teach you all the great things she knows about having fun in the bedroom.

Older women are more confident, more sexually skilled and more interesting than younger women. Of course, with those differences come different expectations.

A younger man has a lot to offer an older woman, but only if he understands what older women want. Use the mindsets and strategies outlined above to consistently turn your interactions with older women into satisfying stories of seduction.


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