Dating An Older Woman | Is It A Good Idea? PROs & CONs

Dating a woman older than you always raise a few eyebrows. Plus, the myths related to older women only add to the fire. It is not a surprise that you have many questions going through your mind. Is it worth it?

Dating an older woman can be one of the most enriching experiences in a man’s life. Older women are more practical and realistic due to their age, which allows you to see a situation differently. She also brings with her a ton of wisdom from prior experiences in life.

Older males are called sugar daddies, and the young women with them are either seen as sweet and innocent or gold-diggers. When it comes to older women, they are called cougars. Do you see the harshness, hypocrisy, and blatant double standards?

Is Dating An Older Woman A Good Idea?

Dating an older woman is a good idea because it allows you to be with a mature person. With age, people tend to get wiser and more patient. Being around someone wise can have a positive influence on your decision-making. You will also learn to deal with situations more patiently and with a cool head.

Not every woman older than you will be controlling and dominating or just looking to use you for physical pleasure.

The cougar stereotype is baseless without any scientific evidence to support it. The choices and actions of a woman are more about her personality than it is about her age.

Age indeed affects how we think and decide, but not everything stems from age.

And even if the stereotype does hold, as long as the two people involved are willing to be together with transparency between them, there is no harm in it.

Is Dating An Older Woman A Good Idea

While writing this article, we took the liberty of making some generalizations for younger women.

The generalizations are based purely on age, our observations and the era we live in.

They are equally true for younger men. Whatever you read below is not a misogynistic rant.

Benefits Of Dating An Older Woman

1. You’ll Be Around A Mature Person

Older women are more mature in almost everything when compared to younger women.

One of the most visible areas is that an older woman learns to look beyond materialistic things as she ages.

Her experience teaches her to appreciate the little things in life, things that money can’t buy.

She is also better equipped to deal with life in a much more practical and wise way.

2. Financial Stability

An older woman brings with her financial independence. She’ll probably have a well-established career, and money won’t be much of a problem.

Why is it important? Money issues make a person cranky and upset irrespective of whatever they are dealing with.

Food on the table is a luxury, and most people don’t realize that. She might even support you once in a while financially.

But, you’d be much better off as a couple if you, too, were not struggling with money. Else, at some point, she will feel like you are using her for money.

3. Increased Pleasure From Intimacy

Women reach their peak of carnal desires later on in life. Not only she becomes experienced, but she also has the stamina for it.

An older woman is quite uninhibited in expressing her desire about what she wants her man to do in bed.

She’ll express her desires vividly as with age, her appetite for lovemaking increases. Thus, older women prove to be better lovers when it comes to physical intimacy.

4. Clarity Of Thought

Older women are quite clear about what they want from life, from a relationship, and you. They do not beat around the bush and are totally against wasting time.

This clarity will save both of you a lot of time in the long run if you want different things from your alliance.

Contrary to the popular but immoral dating advice of playing mind games to get your way, older women like to keep things simple.

Clarity Of Thought

5. Older Women Aren’t High Maintenance

An older woman does not have many demands compared to a younger woman who is full of unchanneled energy.

They aren’t high maintenance and would not expect frequent gifts or demand to go to a club every weekend and express the desire to drink and dance till they pass out.

Older women rather use all that energy to do something more worthwhile with their time and focus on forming a connection.

6. Realistic And Practical

Older women have a ton of experience related to life, and thus they know that life is not a rom-com as depicted on the big screen.

They have practical and realistic objectives from a scenario. They won’t burden you with unrealistic expectations from a relationship.

You would feel a certain sense of freedom when you are with an older woman. They do not have time for drama.

7. Deal Better With Insecurities

An older woman is better equipped for dealing with day-to-day life problems due to the wisdom and experience that comes with her age.

She doesn’t let her insecurities of a relationship get the better of her and takes a wise approach to deal with those insecurities.

It means lesser fights in the relationship and better resolutions. You will also get to learn about life from a broader perspective.

8. Focus Only On What Matters

Whether it is her career, life, money, emotions, or the bond with you, an older woman would only focus on the important stuff that actually matters.

She will have a knack for filtering out the fluff immediately and is a prime example of putting efforts only where they matter.

This means, whatever time you spend with her, it will be an optimal utilization of that time as a couple.

She’ll even be your strong guiding force when you are stuck in a seemingly complex development in life.

Focus Only On What Matters

9. Above Petty Nonsense

An older woman is much less likely to throw a fit about how her hair doesn’t look too good or how that overnight pimple completely ruined her party look.

Older women have their own issues, but they aren’t as unbearable for younger men.

Older women have a lot more to worry about beyond clothes, cars, and losing some followers on social media.

10. Remarkably Confident

Older women have a certain appeal and striking charm. They are particularly confident in their approach, and that confidence will rub off on you.

They are firm with their decisions, and second-guessing is rare because the first decision wasn’t impulsive.

An older woman is also much more likely to follow her plans and will stick around if she commits to you.

11. Aim For Self Reliance

As women age, they realize certain hypocrisy is rampant in society against women.

It is not without reason that feminism and gender equality movements are getting stronger and more vocal every day.

Thus, it seems beneficial to be self-reliant and not depend on anybody for anything, leave alone men.

With a self-reliant person next to you, you can focus on your growth and development without having the burden to carry around someone else’s responsibilities.

This will take a lot of unnecessary stress and pressure off your shoulders.

12. Endless Meaningful Conversations

Lots of experience in life corresponds to more interesting stories to tell.

Talking with an older woman will seldom feel boring as she would have a lot to offer, both in variety and quantity.

You can even go to extreme depths of spiritual conversations trying to explore the meaning of life and everything around you.

She will not get bored and will have a lot of views. Sports, politics, culture, music or fashion, it is highly improbable not to find a common interest with an older woman.

Endless Meaningful Conversations

13. Relaxed And Easygoing

Older women tend to be a bit more relaxed as compared to their younger counterparts. Why?

Because they know the difference between a situation that requires their immediate attention, energy and a situation that looks bothering at the surface level.

They won’t nag you constantly about their worries since they are perfectly capable of handling them on their own.

It is quite probable that she has encountered a similar situation before and knows the way out.

Chances are she remembers her young self in the same situation and knows exactly what she shouldn’t be doing this time.

14. Never Having To Commit Is More Probable

If you are looking for some casual, no strings attached fun, you are much more likely to find it with an older woman.

Older women are often divorced and are not looking for another committed relationship.

All they seek is the carefree, liberating energy of a young man and some good time with no drama.

And if she isn’t divorced, we highly suggest you stay away from her. A cheater is never worth it, even if she is in a bad marriage.

Her focus should rather be on ending such a marriage unless her husband is a tyrant. A married woman is always a tricky situation, and you should always avoid her.

15. More Accepting Towards Their Bodies

Older women are more comfortable with their body shape and size since they have been living with it for some time.

Also, they are much less likely to get affected by what they see as ‘perfect body goals’ on social media.

They know that all that glitters is not gold, and not everything is how it is made to look.

Further, they know that their man will get bored someday if all they have to offer is a hot body.

For older women, looking good and staying fit is more from a health perspective than for photos or the summer beach body.

Thus, they make it a point to invest in developing an interesting personality.

This can be an eye-opener for a man as you learn that a good body is not all that matters after all.

16. Believe In Having A Balanced Life

Older women master the art of having a well-balanced work and personal life.

Life teaches them that anything in excess can never be good, whether it is work, career, or spending time at home.

It is much less likely that an older woman will nag about calling at least 4-5 times a day or responding to texts as soon as possible.

She will know that a person can be busy, and it is not the end of the world if you miss a call or two from her.

She wouldn’t suspect something suspicious is going on and give you a hard time about it because you were online at 2 am but not talking to her.

Believe In Having A Balanced Life

17. Starting A Family Is Not A Priority

The chances are that if she already has kids, she will not be asking you to have more with her.

For younger men, the thought of being a father can be daunting and seem unimaginable.

With younger women, men often freak out because the motherly instincts of most women kick in sooner or later, and they express the desire to start a family.

Young men can be elusive to the idea, and that might cause the relationship to break.

You won’t feel hard-pressed to have kids with an older woman unless she has none and wants some as soon as possible.

18. You’ll Grow As A Person

Older women have more control over their emotions and tend to be more stable. Young blood is usually hot-headed and impulsive.

Once with an older woman, you will grow a lot as a person. Being with an older woman is your free lesson on patience and anger management.

Again she knows most things are not worth getting worried or angry about.

You’ll learn about the art of letting it go and often hear her say, “five years down the line, this wouldn’t even matter.”

An older woman knows what she is talking about, and her emotional stability will be contagious.

Disadvantages Of Dating An Older Woman

1. The Unmarried Ones Seek Quick Commitment

If the woman is well past what society deems to be an appropriate age for marriage and wants to settle down quickly, she will be breathing down your neck to get married at the next chance.

She is not getting any younger, right?

In such a relationship, you will not get much time to know much about the woman before committing to her for something as serious as marriage.

2. Ticking Biological Clock

Just like the unmarried ones, if she has never had kids, she might want to start a family with you.

She knows her biological clock is ticking, and it is only a matter of time before it is too late to become pregnant in terms of safety.

You are in for a world of responsibilities if she is just looking for a man to father her kids.

It also might be possible that she is a recent divorcee or her husband, and her young kids’ biological father is not there for some reason.

In this scenario, she would just be looking for a fatherly figure for her children during their growing-up years.

Moms with kids in their teens are a lot less likely to make such impulsive decisions.

Ticking Biological Clock

3. Might Be Just Looking To Play Around With A Young Man

Be with an older woman only if she genuinely cares about you and you too feel something for her. Don’t be her boy toy or make her your plaything.

The whole portrayal of ‘cougars’ in popular culture, and older women in unhappy marriages lusting for young men, stems from the behavior of a select few.

While the stereotype is too harsh as it puts all couples with an older female in the same bracket, it doesn’t mean that such women don’t exist.

If you want to be someone’s boy toy willingly, so be it. Just make sure you aren’t being used.

4. Unresolved Emotions Due To Her Past

Most older women have had their fair share of relationships or marriages. With all unsuccessful alliances comes their baggage and memories.

Scars from all these bad memories might mar your relationship with this woman. You cannot erase whatever she has experienced.

The unresolved issues and past baggage from her previous relationship can make it difficult for you to connect with her.

5. More Responsibilities To Worry About

Older women have much more responsibilities on their plate, both at work and home. Thus she will have a lot of things going through her head at any given time.

Pressing issues might worry her, which in turn will affect her behavior and your life.

Also, you might find her too engrossed in responsibilities all the time and may feel neglected.

Yes, they master the art of balancing everything as they grow, but we all falter sometimes.

6. Your Family And Friends May Not Like The Idea

Your friends and family might not approve of your relationship with a woman older than you.

Society conditions us to see conventional relationships where the male is older as normal and culturally appropriate.

People challenging this notion do not go down well with large strata of society.

Most of them are myths or beliefs, like something must be wrong with the woman.

Since others see it as taboo, your family and friends might feel uncomfortable and embarrassed to share the fact with the outside world.

You may feel that they are avoiding you.

Your Family And Friends May Not Like The Idea

7. May Not Want To Have More Children

Most older women already have kids and might be reluctant to have more.

Whereas, being younger, you still might have none or be at a point in life where you won’t mind having more with her.

There is no right or wrong in this situation as both of you have valid reasons behind your choices.

If one of you caves in and does what the other wants, it will be a permanent unhappy memory as none of you will be able to come to this point in time again and undo your choice about having or not having children.

8. Power Struggles Can Crop Up

The power struggle is always an issue between couples, and it widens further when the woman is older.

Many younger women accept the traditional (but incorrect) norm that the older male is supposed to lead and will take a majority of the important decisions.

They are not at fault since they have been trained since childhood in subtle ways to accept the gender-based conventions.

In the cases where the woman is older, she is more likely to have a well-established career and finances. With success comes the confidence to challenge conventions.

As a man, you should be open to your woman being more successful than you and not be embarrassed or jealous.

However, draw a line if you feel that the power balance exists in a way where she tries to dominate every aspect of your life just because she is older (and probably more successful) than you.

A good relationship is about equality. You are not fighting to become the next president where the need for having power over the other feels essential.

9. She Will Age And Retire While You Still Work

The age difference can translate into a different age for retirement.

This especially applies to those men who are in it for the long term and not just seeking a short-term pleasure with an older woman.

If she is older, she will retire earlier than you while you continue to work.

After retirement, she will need time to figure out the next step in her life.

You might not be there around her physically or emotionally due to your work when she would be at home for a few days and get bored.

If money is not a problem, she may suggest you retire early so that the two of you spend more time together as she is aging.

Such a suggestion might not go down well with you if you love your work.

10. May Seem Too Practical And Emotionless

Older women tend to develop a no-nonsense, practical, straight-to-the-point attitude as they age.

While this is a remarkable quality to have in a partner, you may find her a bit too practical for your taste when it comes to emotions.

If you fight, you’ll see her get back to normal while you still might be sulking over what she said. You may even assume that she is emotionless and unattached.

But this is not the case. She would just have a different way of looking at a situation and know that sometimes things are not worth spending much time and energy on.

Rather than bickering over something, it is wise to behave normally with each other and let the dispute resolve itself with time if there is no middle ground.

May Seem Too Practical And Emotionless

11. At A Different Stage Of Life Than You

The more the age gap, the more the chances of her wanting something different from this relationship than what you want.

Whether it is about decisions on family, career, commitment, or money, you may find that the two of you have vastly different opinions and needs.

This kind of thing can happen with other couples too. But here, the bigger the difference there is in age, the more it adds to the difference in life paths.

You’ll find that her choice of way differs from the direction you want to go in.

12. Vast Difference In Mental Level

A woman at any given age has the maturity of a man two years elder to her. Thus, a woman at 25 is as mature as a 27-year-old man. Why?

Most of the reasons are deep-seated due to the patriarchy in the society, which forces the child in a girl to take a step back and see things as an adult.

The other reasons have been explained in this study by Newcastle University, England.

When the woman is also biologically older than you, you’ll feel the difference in maturity quite clearly.

Extreme differences in age within a couple make things even more difficult if the female is older since it increases the maturity gap by biological age plus two years.

Disagreements can become frequent due to completely different approaches, energy levels and outlooks because of age.

13. Age Gap May Become Cultural Gap

If the age gap is too much, it transforms into a generation gap. From the generational gap stems the problem of the cultural gap.

You will find it difficult to have common favorites when it comes to movies or a T.V. series. Okay, we are not talking about Friends, as it is everyone’s common connection.

But you get the gist. Choices of music, favorite actors, actresses, sportspersons will not just differ in genre but also in the sense of a complete generation.

Political views and what’s culturally appropriate may become other points of friction.

14. Health Issues Due To Aging

As she ages, various health issues are bound to surface. It is something unavoidable.

Being older than you, her struggle with an illness will be longer and have lesser chances of success.

One of the worst ways to see someone go is when they die in your arms.

It is a memory you will never be able to forget. If the age difference is a lot, you will probably outlive her.

She will die before you, and the remaining years of your life will feel like a struggle without her.

Health Issues Due To Aging

How Much Of An Age Gap Is Ok?

An age gap of 5-15 years is ok as it gives you several benefits of dating an older woman and minimizes the health-specific disadvantages. Dating a woman who’s not 5+ years older feels like dating someone around your age. Dating a woman 15+ years older may feel like a generational gap.

However, this doesn’t mean that couples who lie outside the defined age bracket cannot make it work.

It all boils down to the understanding between the two people in question at the end of the day.

Sticking to the age bracket is suggested to lessen the burden from problematic areas.

Exceptions and outliers will always exist, and they play a major role in making society more accepting of such relationships.

A young man with an older woman would always look weird to someone who hasn’t seen a beautiful couple work things out.

Even if such relationships do not succeed, attributing the split purely to age difference feels very narrow-minded.

Any relationship, successful or unsuccessful, depends more on the nature of the people involved. Accepted norms should be questioned time and again.

What’s normal to one may not be normal to the other. Sometimes there is no wrong or right.

How Do You Deal With Dating An Older Woman?

Deal with dating an older woman by not second-guessing yourself at every turn. If she is with you despite the age difference, it means she saw a man in you. Women have a knack for filtering out boys from men. Even if society says otherwise, you can have a perfectly normal relationship with her.

Here are a few more tips:

1. Don’t treat her like she is your mother. Does she treat you like your son? If yes, you are heading towards failure as a couple by strangulating the space for romance.

2. Do not emphasize the age difference even unintentionally. She is well aware and hears about it from every other person. If anything, it will make her feel old.

3. Advancements in medical science like in-vitro fertilization have made it possible for older women to have kids. No pressure there. Do not force her to start a family with you as soon as possible just because you want kids.

4. Don’t rush her into physical intimacy. Take it slow as you would like with any other woman. If she wants things to be quick and you aren’t comfortable, feel free to say no and walk away.

5. The decision to get married is a big one. Do not rush through the process just because she is at a certain age. Let the two of you understand each other first.

6. Always be honest about why you are with her. If one of you is in it for some quick fun, but the other expects commitment, don’t fool around. A heartbreak can crush you, whatever your age is.


Do not fret too much over the age of a woman. It is how she is as a person that would matter in your everyday interaction with her.

Just because everyone around you sticks to conventions doesn’t mean you too have to do it.

Be open to dating an older woman and experience what only a few men ever get to feel like.

Form your own opinion through experience and not on what others have to say. If nothing else, it will make one hell of an interesting story.

Shashank Verma

A trained theatre actor and a STEM graduate who brings perspectives and methods from these worlds into dating and relationships. Also a big time Krav Maga enthusiast and practitioner.

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