How to Date Older Women (Cougar Dating) - Cool Dating Advice

How to Date Older Women (Cougar Dating)

Older woman dating a younger man

Are you the type of guy who spends a considerable amount of time thinking about older women? If so, then you already know what makes an older lady so attractive.

What you might not know is how to land that ever so important cougar of your very own.

You see, dating older women is a whole different process than someone your age.

The method of not only selecting an older woman but finding the right one to date can seem like a huge challenge at first.


Make no mistake about it, every guy reading this can meet up with the older lady of his dreams as long as he follows a few easy steps.

First off, let’s talk about the pros and cons of dating an older woman

An older woman knows what she wants out of life

Here are the pros

Time is the best teacher of all things, and life is one of them. A woman who is significantly older than you will have a more stable head on her shoulders.

She will know what direction in life that she wants to go to. If you’re struggling to find a path forward in your life, dating an older woman may assist you in heading in the right direction.

Older women tend to be more financially secure

No young person makes good money, and that’s the way it is for almost everyone. A person must have a few years under their belt before making any serious money at their job.

The average person who makes good money at their work first invested quite a bit of time into receiving an education.

No matter what education level you are, it’s still going to take at least a decade to find a financial groove.

Dating an older woman, you are avoiding those wasted years, and you get to enjoy the fruits of her labor right away.

Experience matters when it comes to the bedroom

Oh yeah, this right here is the reason why many guys like older women. You might be less sexually experienced, or you could be the type who doesn’t want to teach a woman what to do.

Older women have been around the block a few times, and they know how to please a man.


Sex is something that takes quite a bit of practicing to become a master. It’s next to impossible for a woman to know how to satisfy a man without learning the tricks of the trade.

Pleasing a man is a learned skill, and it takes quite a bit of experience in the bedroom to put a smile on a man’s face.

Now let’s turn our attention to the cons

Older women have less free time

Between family obligations and work, an older lady doesn’t have time for much.

A younger woman has much more time for dating, and all that goes along with falling in love.

You must accept a smaller slice of the pie when it comes to the amount of time that you’ll spend with your older girlfriend.

If you’re a needy person who is constantly needing attention, you won’t find it with a mature woman.

She is far too busy to babysit you and drown you in attention and affection.

Your friends will think your new girlfriend is weird

Admit it; you care what people think. How will your friends react to you dating a much older woman?

Your friends are going to be shocked, and quite a few of them might not accept your new girlfriend.

Can you blame them?

The level of their shock will be determined by the number of years difference in age there are between the two of you.

A couple of years aren’t a big deal, but when you’re talking about decades, that’s when perceptions begin to change.

If you can handle the stares and possible ridicule by those who you call your friends, then dating someone much older than you shouldn’t be that big of a deal.

Your girlfriend might have children your age

Let’s say you’re 20 years old, and you have a thing for women who are 40 plus. She might have kids that are your age or older.

How awkward would it be to sit at the Thanksgiving table with your girlfriend’s daughter, who is a few years older than you?

It’s going to take you some time to get used to feeling younger than your girlfriend’s children.

Just think, if the two of you get married, you’ll be the stepparent of children who are older than you.

If you watched the movie Four Christmases, then you know this is true when Vince Vaughns mom is married to Vince’s best friend from high school. In the movie the whole thing is very awkward.

How to impress an older woman

Now that you’ve made up your mind that you want to date an older woman putting the moves on her is the next step.

You should be well aware that a seasoned lady is someone who has seen it all. Fast-talking pickup lines don’t work on older women like they do on other women.

You’ve got to work to be noticed by a woman who has seen it all.

Be confident and don’t lose your confidence

You’ve got to stay confident throughout your stride. You pour on your confidence from start to finish without ever doubting yourself.

An older woman is someone who reacts to confidence much more than someone half her age, and you must remember this.

She wants more than anything to have a partner who sees himself as her equal. Age doesn’t matter as much to her as your level of confidence.

Make the first move

You might think that an older woman is old fashioned than the girls your age, but that couldn’t be further from the truth.

The older women you approach want guys to make the first move, and they expect it.

If you’re waiting for an older woman to put the moves on you, then you’ve got another thing coming.

Take the bull by the horns and be the first one to ask the other out on a date.

Small talk is excellent in the beginning, but you’ve got to set your sights higher than only talking to her.

Show her your independent streak

The woman who you have your sights set on doesn’t want to be your mother. She wants to know that you’re capable of taking care of yourself.

Talk up your achievements and all the things that you’ve accomplished in your life.

If you have a good job, make sure to tell her about it. If you’re still in college, then talk up how excellent your grades are.

Whatever you do, make sure she knows that accomplishments drive you. If she feels as if you require babysitting, then the relationship is a no go from the start.

Always look your best

You want to go beyond wearing nice clothes and smelling good.

Make double sure that every hair on your head is perfect. Go to the barber often and iron your clothes.

The impression you want to give is that you care about your appearance. You can’t go overboard in this respect as it will show her that you’re taking your life seriously.

The major problem women have dating a younger guy is they don’t want to be a motherly figure.

The woman must feel as if you aren’t going to weigh her down with a lot of baggage.

Your appearance will go a long way in convincing her that you’re not some snot-nosed kid who will cause her headache after headache.

How to keep a mature lady once you’ve whisked her off of her heels

You’ve done all the right things to get the mature woman of your dreams. Now you want to make sure that she’s yours for good.

Well, maybe not for good, but for long enough to make dating her worthwhile.

Some of you may be looking to get married while others are wanting a steady relationship without the baggage of marriage.

Regardless of what you’re searching for, you will want the relationship to grow legs and be around for a while.

Show her your dedication by taking your life serious

Dating an older woman is much more work since you always have to prove yourself. She is going to want you to work all the time.

You can’t go from job to job like you would with a younger woman. You will need stable employment or at least study full time as a student to prove that you’re taking your life seriously.

Anything short of that and the woman is going to think you’re a flake and not worth her time at all.

Go out of your way to show your appreciation

You can get by without buying flowers for your girlfriend if she’s a college student. An older woman, she’s going to expect you to spend your money on her.

That means you will need to buy her flowers, take her out to dinner, and part ways with your hard-earned money.

Be overly romantic and take it to the next level

Do you want to have your mature girlfriend eating out of the palm of your hand? Be super romantic and do all the things that you see in those corny comedy movies involving couples.

Don’t shy away from showing your love for her both physically and verbally.

Write your woman a poem and print it out on fancy paper and put a rose on top of it. The things that girls your age would think of as being sappy, older woman eat that stuff up.

Take it nice and slow in the bedroom

Older women are like older cars in that it takes them quite a bit of time to get warmed up.

A younger lady will go from zero to sixty in a mere matter of moments. It takes a mature woman a lot longer to get all hot and bothered in the bedroom.

Take your time and don’t rush things when you’re in the bedroom with a mature female. Be nice and slow, and make sure that you pay attention to every aspect of her body.

She will be like putty in your hands if you’re able to please her.

Most younger guys believe the best thing to do is a sprint to the finish line, and she will love the fact that you’re the type who is willing to go at a snail’s pace if it’s required.

How old is too old to date?

Let’s say you’re a guy in your 30’s and you’ve got a serious crush on a woman who is 65. Is she too old for you?

There is no one size fits all answer to that question.

Many will immediately see that she is over twice your age and think that it’s outrageous that you’d want to be in a relationship someone her age.

There are a few key things that you need to ask yourself when dating someone considerably older than you.

Do you want to have children?

If the woman is beyond childbearing age, then having children with her is out of the question. If you are hoping to start a family, then adoption will be your only option.

She might be too old to adopt kids since it takes a lot of energy to raise a child.

Do you care what people will think?

Does it bother you when people say stuff behind your back? If it does, then dating someone much older will cause people to say all kinds of things.

Remember, people often find these sorts of relationships shocking, and their reaction to them is usually over the top.

Are you okay with someone not having as much energy as you?

If you’re 25 and dating someone who is 30, a lack of energy isn’t a concern. If you’re 25 and dating someone who is 50, then yes, energy levels are a concern.

It’s stupid to believe that a 50-year-old will be able to keep up with you if you’re 25.

The bottom line on the age difference

There is no age that’s too old if you’ve found Ms. Right. It’s your call and only yours if you want to date her.

Put all things into perspective and then ask yourself if it’s worth it. If you find that it is worth your time to pursue a relationship with a mature woman, then give it a try.

Who knows, you might find yourself having the time of your life with a woman who can teach you a thing or two.

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