Dating an Older Woman: 45 Pros, Cons, Myths & Secrets to Impress & Date Her

There are a lot of misconceptions about dating older women, but for every misconception, there are twice as many perks! Read on to find out just how wrong these misconceptions are, and maybe why you should consider dating an older woman.

dating older women

Older women dating younger men sometimes cause more buzz than seeing an older man flaunting around a girl that looks like she could be his daughter. Despite age being “nothin’ but a number,” there are a multitude of misconceptions about the idea of younger guys dating older women.

Whether you agree with these ideas or not, one thing is for sure — an older woman knows what she wants in a man and she won’t settle for anything less. [Read: Healthy relationship – 27 signs, qualities and what it looks like in real life]

How to impress and win over an older woman

It doesn’t come solely down to popular media as to why this particular relationship dynamic occurs so commonly. There are some fairly solid reasons as to why the older woman and younger man make such a good match.

Sexual and physiological factors are prime reasons. With men hitting their sexual peaks between the ages of 18 and 21, and women somewhere around their mid to late thirties, the conclusions drawn from this particular set of realities are obvious.

If you’re keen to date someone who knows what she wants, read on for a few vital tips on the age-old art of seducing and securing the attention of an older lady. [Read: Science of attraction – 17 things that are far sexier than looks]

1. Dress to impress

The average older woman has been around the block a few times. She’s seen more than you have, heard more than you have, and experienced more than you have. That also means that she’s experienced a much wider range of social situations than you, and she knows how to dress for each and every one of them.

It is paramount that you get the dress code right whenever you are in her presence. Making the mistake of wearing a t-shirt to a smart, casual event or a tuxedo to one that requires full morning suit attire is likely to leave her feeling distinctly underwhelmed. [Read: The steps to follow to be the sexy guy you’ve always wanted to be]

2. Stick your chin out

You’re a young guy, and that’s a major part of the attraction for older women. They like who you are — all that freshness and youthful spirit — and don’t want you to pretend to be anything else.

Irrespective of age, there are certain traits that women need to see in the male objects of their affection. You could be 18 or 80, but she still wants you to be a man — a confident alpha male with a keen eye and robust set of opinions.

Be strong and show her that, despite your tender years, you know your own mind and are more than willing to share it. [Read: How to be manlier but not aggressive]

3. Know when to keep quiet

This particular point is the opposite of the previous one and counsels you to keep your mouth shut on occasion. That’s not to say that you shouldn’t air your opinion from time to time; she actually likes that.

What we mean is you need to learn the importance of allowing free discussion on both sides. Some young men try to dominate the conversation, but such a forceful and uninformed manner is unlikely to impress the independent and savvy older woman.

4. Avoid the obvious

Although she is an older woman and this rather apparent age gap lies between you, that doesn’t mean she wants to be constantly reminded of the fact.

Silly references to her being a MILF, cougar, or hot mom will not impress her, and will probably mean a stingingly swift slap across the jaw.

If you want to charm her, talk about her apparel, her wit, and her beauty. [Read: Age gaps – The new trend in relationships]

5. Compliment her

The older woman is a lot smarter and more keen-minded than your own age group. But she isn’t so bitter and cynical that she doesn’t know how to appreciate the odd compliment.

In fact, as she passes through her middle years, she’s probably more receptive to her ever-dwindling supply of compliments than ever before. Make her glow with a few well-chosen words describing your appreciation for her, and watch her melt in your arms. [Read: How to compliment a girl and make her blush]

6. Avoid flattery

There’s a huge difference between the act of paying a compliment and the act of attempting flattery. The former is a genuine attempt to express your appreciation for someone’s physical or cognitive attributes, and the latter is merely a form of deceit.

Don’t forget you’re dealing with an older woman, here. She’ll smell the BS in seconds and have you running for the hills, with your tail tucked firmly between your legs, if you offer anything less than the whole truth.

7. Stay trim

Let’s be honest, here, one of the reasons you can get into cougar panties when your older counterparts have failed is your youthful vigor and physique.

If you let yourself go and start getting a bit heavy around the edges, or short of breath at the briefest hint of a stiff walk, then you’re giving away your greatest weapon. [Read: 28 self-improvement secrets to improve yourself and transform into your best self]

8. Location, location, location

At some point, you’re going to have to take her out on a date, which can be quite daunting, considering her experience in this field. Just remember: she’s no fluffy bunny, but a strong, confident woman who knows her own mind.

Take her to the kind of place a woman of her age deserves and expects — somewhere swish and impressive — and save the burger joints for the twenty-somethings. [Read: Date ideas men love but women actually hate]

9. Games ain’t for dames

Always treat your lady with respect. Game playing is so far beneath her that it probably resides somewhere in the vicinity of the earth’s core. If you say you’re going to ring her on Tuesday, then ring her on Tuesday.

Playing some kind of “treat them mean and keep them keen” routine is not going to work on this lady and could backfire on you with spectacular effect.

10. Give her some space

As an older woman, she has her own life, and this needs to be respected. That late teen/twenty-something puppy love routine has no place in the life of a mature and independent woman of the world.

Throwing yourself upon her at every possible juncture will make her feel stifled and crave the presence of less-demanding company. [Read: 15 ways to give space in a relationship and feel closer than ever before]

11. Meet her where she is

Older women have a stronger sense of who they are, so don’t try and make her try to be something she’s not. If anything, she’s more likely to move on because she won’t take someone trying to make her change.

So, talk to her about things you know she’s interested in and learn from her, rather than trying to get her to discuss things she’s not into.

12. Don’t pursue her just because of her age

Don’t assume that dating older women is going to give you a badge of honor or something similar. You have to do this because you like the woman in question and nothing more.

Don’t pursue her just because you think it makes you look good in front of your friends. [Read: Why do men like a chase?]

13. Be prepared for rude questions

People are judgmental and especially when it comes to older women and younger men. It’s wrong, but that doesn’t change the fact that it happens.

If you’re serious about dating this lady, know that you’re going to have some rude questions coming your way. Once you make peace with this fact, you’re better placed to side-step them and tell people to mind their own business.

14. Make sure you’re on the same page

If you’re not looking for anything serious, make sure you’re clear about this. If you are, also make sure you’re clear. It’s important to make sure that you’re both on the same page here.

This matters more when you’re dating an older woman because she’s less likely to be looking for a casual hookup. She might be, but it’s not quite as likely as if you were dating someone younger. [Read: What are you looking for in a relationship?]

Pros of dating an older woman

By the time a woman has reached a certain age, she’s had enough of chasing around, being taken for granted, and wasting her time. She’s over the games and wants something fulfilling, whether that’s for the long or short-haul.

So, what are the pros of dating an older woman?

1. Older women usually know what they want

By this time, older women know exactly what they want and what they don’t want. That means no confusion. There’ll be no wondering whether she likes you or not, she’ll outright tell you.

2. Older women usually have less drama

This isn’t always the case, but generally speaking, older women are over the drama and keep everything as simple as possible. [Read: Dramatic diva alert – All the signs your girl is a drama queen]

3. An older woman has more life experience

Need advice? Check! Not sure what to do? She’ll help you out!

4. Older women are generally more financially stable

She has her own money and you’ll never have to wonder whether her reason for being with you is financial. She’s also less likely to be up to her eyes in debt.

5. Older women are strong conversationalists

When someone has life experience, they have a lot more to talk about. Also, age brings confidence and a sense of knowing who you are.

All of this adds up to fantastic conversations. [Read: 45 happy ways to keep a conversation going and be a lot of fun to talk to]

6. Older women are more independent

You’re not dealing with a 20-something-year-old girl who just moved out of her parent’s home and is still finding her feet.

Instead, you’re dealing with a woman who has been taking care of her own for long enough to be a pro by now. She knows how to do it all, and do it all herself.

Independence is super-sexy, right?

7. Older women are more appreciative

That doesn’t mean she’s appreciative of everything, but when you treat her right, she’ll show her appreciation. Through life experience, she might, unfortunately, know what it’s like to be treated badly.

8. Older women have more experience in bed

More experience means she knows what she wants between the sheets and that’s certainly an attractive trait! [Read: Curious minds want answers – How many sexual partners is too many?]

9. Dating an older woman can be an ego boost

But that’s not the main reason why you should do it.

Cons of dating an older woman

Of course, it’s not all sunshine and roses dating anyone in this world. Whether she’s older or younger, there are going to be hard times. But, there are specific cons that are associated with dating an older woman.

1. People are going to judge you

Sorry, but it’s true. We live in a cruel world where people tend to enjoy judging others.

2. You’re at different stages in your lives

This may or may not be a problem, but if it is, it could be a deal breaker that forces you apart. [Read: Relationship compatibility – What it is, 40 signs you have, and ways to improve it]

3. It won’t work if you’re not emotionally mature

To successfully date an older woman, you need to be emotionally mature. This can be a problem for some younger men!

4. Older women may have baggage

Maybe she’s been married before, perhaps her ex won’t leave her alone, or maybe she has children. Basically, with more life experiences comes the possibility of more baggage. This may or may not be a problem for you if you’re looking for low commitment or low stress.

5. There may be issues if you want children

Depending upon how old she is, there may be problems if you want children. It might also be that she’s still young enough to have children but she just doesn’t want them at this stage of her life. [Read: How to know if both of you are ready to have a baby]

6. She may be looking for more than you can offer

At this point, she’s probably not looking for a fling. She might be, but she may also be looking for a life partner. If that’s not what you want, it’s not going to work.

The misconceptions about dating older women

These myths often originate from an outside perspective and very few are actually based on solid facts. Attraction exists between people of any age, and a relationship with an age gap doesn’t mean that it’s temporary, strictly about sex, or part of an aging woman’s mid-life crisis.

Here are some of the most common misconceptions about dating older women:

1. They won’t have anything in common

When it comes down to couples with an age gap, people assume a younger dude and an older lady have nothing in common. It’s almost as if they think the guy will be immature and she won’t mesh with his taste in music or hobbies.

People think she was born on another planet or lived in a basement for 30 years with no access to the outside world, television, or radio.

The reality is, people of all ages have things in common. Even if they don’t, they probably stand to learn a few things from their younger/older partner. [Read: Cougar dating: Rules about dating an older woman]

2. They have different views on children because of the age gap

Even if she has kids from a previous marriage, it doesn’t mean she wouldn’t want to ‘breed’ with someone younger that she cares about if they decided to have children together.

Some young guys want kids, some don’t, so it’s not safe to say all relationships with an older woman are fraught with arguments about children. Some women don’t want children either!

3. If the woman has kids, a younger guy won’t want to take on all that “baggage”

Believe it or not, plenty of men take on children from their partners’ previous marriage/s regardless of how old they are. This is not an issue for all young guy/older female couples.

Instead, it’s just a matter of two people and how they handle baggage from previous relationships. It also depends on how much they care for one another. [Read: Emotional baggage – How to help someone put it down and find freedom]

4. A younger guy will cheat on an older woman with someone younger

If a younger guy has a thing for older women, why would he choose to cheat on her with someone younger? The idea that a younger guy eventually wants a woman devoid of wrinkles or stretch marks is ridiculous.

The same way a guy dating a girl his own age might cheat on her for a more experienced older woman… point proven. [Read: The reasons why passionate love can be the truest love of all]

5. An older woman targets younger men for sex

The stereotype of the older woman, dressed up and drenched in perfume, waiting at bars to lure young men into her trap, is not the reality. Rather, younger men are often the ones pursuing attractive older women.

He finds them to be respectable, mature, cultured, and self-assured. Therefore, the younger man will most often be the one pursuing, generally not the other way around.

6. She will get older and less attractive

Typically, if the older woman got a younger guy in the first place, it must mean she’s attractive, exudes a youthful spirit, and displays a zest for life.

She probably takes great care of her body, health, and hygiene, and takes pride in her physical appearance.

Age doesn’t mean becoming unattractive. As she ages, so will he. What really matters is the connection they have and how their personalities mesh. [Read: Does true love exist: Signs that might make you a believer]

7. She will have too much free time while he’s establishing himself

This point makes it seem like older women don’t have jobs, social lives, or any ways to occupy their time. It assumes that an older woman who’s already established herself in her career will quickly become bored and lonely while her younger man establishes himself.

This couldn’t be further from the truth since she probably has a variety of people and pastimes to fill in the gaps while her guy works. Oh, and unless she’s retired, she’s probably busy working too!

8. An older woman won’t fit into a younger guy’s social life

At first, the relationship might cause a few raised eyebrows. But if a younger guy’s friends don’t take his relationship seriously, then they probably aren’t good friends.

True friends accept their friend’s partner, or at least do their best to get to know her before making a judgment based on age.

If she treats him well, they will probably just be happy that their friend found a quality partner. [Read: How to read the signs your boyfriend’s friends don’t like you much]

9. Younger guys only want an older woman for a fling

The idea that younger guys only see older women as a sexual conquest to get under their belt is not always true. While some cougar and cub relationships might begin this way, there are plenty of examples of younger men who choose to seriously date older women.

It’s just the same way younger women might want to date an older guy for his maturity, stability, and wisdom. An older woman is attractive to a younger guy because she’s straightforward, confident, established, and usually has a good head on her shoulders. [Read: Age gaps: The new trend in relationships]

10. She won’t be able to take him seriously

Not all younger guys are immature losers who do dumb things for attention and can’t keep a job. Many younger guys are actually responsible, well-rounded, mature, and focused on their careers.

They want a woman with whom they share a mature relationship, minus all the headaches associated with a girl his age.

This is where the older woman comes in and finds him charming and fun, but also serious and focused. These are attractive qualities in a partner of any age.

11. Her kids will hate him

If an older woman has kids from a previous marriage, there is always the initial bewilderment when they find out she’s dating someone other than their dad.

The other shock can be when they find out he’s a lot younger than their dad, and might not even be that much older than they are.

However, if they see he’s a good guy treating their mom well over the long term, they will learn to accept and respect him. [Read: Family orientated – The meaning and what it means to be this person]

12. His parents will hate her

There’s always the odd stigma attached to the thought of a young man being lured by an older woman that makes parents cringe a little. They wonder what’s wrong with her that “she can’t get someone her own age.”

When they realize it was their son who did the chasing and that he has an interest in older women, they might begin to ease up a little.

When they see she brings a lot more to the table than a younger girl, they begin to see just why she could be a great match for their son. [Read: Clear signs its the right time to meet the parents]

13. The relationship is an unrealistic fantasy that won’t last

It’s a long-standing misconception that the older woman/younger man relationship is based on fantasy and nothing real. It’s all about a young guy’s crush on a more sexually experienced woman, and an older woman’s craving for a younger, more sexually agile man.

However, more and more young men are dating older women and settling down with them for the long haul.

When you have an attraction and chemistry with someone whom you feel comfortable and close with, why shouldn’t that relationship flourish, regardless of the age difference? [Read: Dating someone younger than you: How to make it easier]

How to maintain a healthy relationship between an older woman and younger man

Maintaining a healthy relationship with an older woman is not much different from any other relationship. However, there are three specific steps to bear in mind:

1. Open and honest communication

An older woman doesn’t have time to sit around wondering what you think or feel. She wants you to tell her. For this relationship to work, open and honest communication is key.

Stop with the game playing and expecting her to read your mind. Be prepared to put everything into words. [Read: How to communicate better in a relationship and fix a lack of it]

2. Maintaining intimacy in the relationship

Now, intimacy doesn’t only mean sex. That’s one part of it, but intimacy is also about showing how you feel in other ways, such as hand-holding, cuddles, and words of affirmation. It’s important to show her how you feel by keeping the fire of intimacy burning.

Of course, that also means keeping your sex life as hot as possible!

3. Respect for one another at all times

Respect works both ways, and for any relationship to work, you need to make sure that you’re both respecting one another.

This is especially important when you’re dating someone older because this woman isn’t going to stand for someone disrespecting her. Once that happens, she’s gone. [Read: How to show respect in a relationship and love each other better]

Age really is just a number!

If you meet an older woman, connect, and start to feel all fuzzy toward her, go for it! Don’t let age get in the way and don’t allow judgmental comments from others to stop you from experiencing what could be true love.

[Read: Rules of etiquette for the modern gentleman]

Great relationships can occur between any two people regardless of an age gap. These debunked misconceptions about dating older women are proof that a woman’s age holds no bearing on whether or not she can maintain a relationship with a younger man.

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Vinod Srinivas Serai
Vin Serai
Vin Serai is the founder of, and has delved deep into the working of love and relationships for almost two decades. Having dipped his feet in almo...