Skip to content

How To Date A Woman In Her 40s

How To Date A Woman In Her 40s

How To Date A Woman In Her 40s

Is dating nowadays ever straightforward?

It seems like to first make a connection an application must be downloaded, a match must be made, and only then can a conversation begin. Hitting on women in bars feels outdated and forced during a time when men and women are less social than ever.

The aforementioned dating oddities only compound the act of dating a woman in her 40s. In the modern dating landscape not only are there more single women in their 40s than ever before, but men in their 40s, 30s, and even 20s are considered potential suitors. What does it mean to chase a single woman of seasoned age?

How exactly do you date a woman in her 40s? Below is a breakdown based on different male age brackets.

Why Date A Woman In Her 40s?

Dating 40-year-old women is awesome.

There are just things that older women have in abundance that younger women don’t.

Here are just a few of those things.

They Know Who They Are

These women have had 40+ years to figure out who they are. You won’t see them constantly changing jobs, moving from city to city and man to man. They won’t lack confidence, second guess themselves, or act a fool. They’re more than comfortable in their own skin.

They’re Independent

Gone are the days of having to worry about some girl you’re dating using you for your money or you going broke spending big on every date.

The women you aspire to date have their own money, worth, and lives.

They don’t need you, rather they want you. 

They’re Stimulating

Have you ever dated a woman substantially younger than yourself?

You may have noticed signs of immaturity, naivety, and superficiality.

These are traits that everyone has regardless of age. Thing is, they’re just easier to find in young women and men.

No more having to pry her attention away from IG as you try to make conversation. One of the many boons of dating an older woman is that the conversation will flow as they pull from their wealth of knowledge and experience.

She Knows What She Wants

What 40-year-old women want is obvious.


Because they’ll tell you.

She doesn’t want to waste her time. She knows how to communicate her desires to you and she will. Let’s just hope you can handle what she’s asking.

When You’re A Man In Your Early 20s

The first question that a skeptical friend might ask you, is why you’re attracted to a woman in her 40s? It’s a reasonable question. If we take evolution into account it almost doesn’t make sense. A woman in her 40s has her best childbearing years behind her, she’s physically less in shape than a woman in her 20s, and has fewer years left to live than a girl your age. Yet if he were able to look beyond such reasoning he would see that there are a host of reasons why a younger man would go for an older suitor.

Here are just a few reasons young bucks find women in their 40s to be awesome romantic companions:

  • Excellent communication skills
  • Wealth of knowledge
  • Mental maturity
  • Don’t want to have (more) kids
  • Are financially stable
  • Know what they want
  • Intellectual

Each individual will have their own unique reasons for dating an older woman. While the aforementioned are traits typically assigned to older women, let’s remember that each woman is unique and offers something that other women in the dating pool don’t. Whatever the case may be, you have your reasons for being interested in an older woman. Now it’s time to learn how to date a woman in her 40s.

Be Ready For Physicality

Most 40-year-old women don’t settle down with men in their early 20s. But is this what you’re even looking for? You make her feel young again. Part of making someone feel young involves physical contact, and lots of it. Don’t make the assumption that carnal pleasure is all that she’s after. That being said, certainly be ready for the possibility that what she finds most attractive about you are your sexual, not financial, assets.

Be Prepared For The Looks

Know how to deflect and use wit to diffuse awkward and even hostile situations. When acting romantically in public, you two will be given your fair share of odd looks. Use humor to make the best out of these uncomfortable situations. If you can’t handle being the recipient of condescending comments perhaps you don’t have the mental fortitude to date a woman in her 40’s.

Should a situation arise where a mean-spirited comment is said be prepared to show your lady that you’re proud to be seen with her. If you let your embarrassment be shown she most likely won’t stick around for too long.

Take A Back Seat To Her Children

You’re not the most important man in her life. She may have a little man or two that are in need of her almost constant attention. Get used to being the second most important man in her life. If you can handle not being a priority, this relationship might last.

If you plan on dating a woman in her 40’s for an extended period of time, chances are that you’ll meet her kids. How will you respond when you are being slot in for daddy duties? Are you willing to adopt her kids as your own as the relationship progresses?

She Wants A Mature Man

Just because she’s dating a younger man doesn’t mean she wants to return to her sorority days. Don’t expect her to be up for L rides with the boys or spontaneous trips out of town. Her life’s tempo might be slower than yours. Do you know how to slow your life down so that it aligns with her pace?

Be Aware of Baggage – Dating Women Over 40

If the 40-something woman you’re dating has been largely single all of her life, there’s likely a reason.

She might be so jaded by now that she doesn’t see much hope in finding a long-term relationship.

Or her standards might be so high, no one can ever match up to the fictitious creature she’s created in her imagination. Similarly, you might also be dealing with a woman fresh out of a divorce. Either way, you could wind up with more baggage than you anticipated.

As such, it’s important to MegaDate.

While I don’t recommend searching for the unicorn that has no baggage (because you’ll be looking for a long time) I do recommend MegaDating so you can compare each of the women’s baggage to one another.

Some baggage can be manageable, while others are the kiss of death. It’s good to compare and contrast to see whose baggage is a fit for yours so there is a mutual understanding and compassion.

When You’re A Man In Your Late 20s

Most of the same rules that apply to a young 20-year-old apply to one in his late 20s. The difference is when it’s a 29-year-old man that’s dating a young 40-year-old woman. With an age gap of slightly more than 10 years the relationship can take on a more serious tone. Instead of you being seen as fling material she might consider you to be a serious long-term option. Are you ready for this or are your MILF fantasies getting in the way of seeing her as a long-term partner?

Ask Yourself The Big Questions

As I mentioned before, 29 is now the most average age for an American man to settle down. Naturally as you approach this age you’ll start to think more and more about what you want in a long-term partner. You will begin to ask yourself if this 40-year-old woman is a serious option going forward or if she’s just a fling.

I’m in no way urging you to settle down at 29. But the reality is that as you age the dating pool shrinks. Do you really want to potentially waste years of your life dating someone that you don’t seriously think you have a future with?

When You’re A Man In Your 30s

Long-term relationships are most likely to work out when dating someone within 10 years of your own age. The generational gap isn’t that much of a hurtle, you both have gone through similar experiences, and are more likely to have your life goals and lifestyles aligned.

Dating someone more than a decade younger or older widens the generational gap to a difference that’s difficult to manage. Finances, relationship goals, music, and lifestyles are likely to be too different to manage.

Romantic Expectations

How to date a woman in her 40s becomes a more seamless process as you close the age gap, though there are still some issues to contend with. At such an age difference the idea of a fling becomes less likely. After a few dates you might want to have a conversation about what the other person is looking for. Are they sold on the idea of marriage and monogamy or do they never intend to settle down again.

Women in their 40’s are less likely to be scared off by this conversation than a 20-something is. Having the talk early on in the relationship will ensure that you’re not wasting anytime dating someone that doesn’t have the same relationship aspirations as you do.

The Kid Talk

The average American male has his first child at 31. You’re entering the age where you’re seriously considering having a child. She on the other hand is entering the age where it’d be dangerous to bear a child. Are you okay with never having a biological child of your own?

This isn’t a conversation that you’ll want to have after a few years of dating a woman that’s already in her 40s. This conversation should be had at the beginning of the relationship so you know that you’re not investing time in a relationship that ultimately won’t work out.

Ready For Integration

Women in their 40s already have a vibrant life. They have children, a mortgage, perhaps an ex-husband, social groups, habits, etc. You won’t be able to erase the life’s she built. Nor will you have the ability to create many things from scratch i.e. a biological family and purchase a home.

When you date a woman in her 40s with an already established life, you’re accepting much more than just the individual. Are you ready to accept the many sentient accessories that accompany your new love?

Be Direct When Dating 40-year-old Women

Women in their 40’s want men who are straight-shooters and who can communicate as well as they can. 

By now, both parties have likely had their share of dating disappointments and have learned how to navigate heartbreak.

Rather than engaging in the immature mind games you did when you were in your 20s, be upfront about your intentions. 

Let’s say, for example, you recently got divorced and you know you’re not ready to jump into anything serious just yet.

But at the same time, it’s been a while since you were physically intimate with someone.

My recommendation for you is that you say something like this…

“I’m really enjoying getting to know you and I would love to explore physical intimacy but I know that I’m not ready for anything serious because I just went through a divorce and I need some time to relearn who I am and what I want in my life.

I want to make sure I’m managing expectations well and that we’re both on the same page before moving forward. How are you feeling about everything?”

Being direct like this can feel foreign because we’re often afraid to communicate our intentions directly. But doing so will increase the respect she has for you and will save you from mismanaged expectations down the line that can lead to hurt feelings, stalkers, and fights.

Give her a little time to think your offer through. 

Oftentimes, when a woman has time to really think through what you’ve said, she’ll end up deciding that she’s cool with it and will appreciate having all the facts before making her decision.

Just make sure that if you’re dating women over 40 you know how to use tact and are an expert communicator. 

Make Sure You Take Responsibility for What Went Wrong In Your Past Relationships

What 40-year-old women want is a man. 

That means a guy that owns up to past relationship failures. It means a guy that has learned from his mistakes and is now a better partner than he once was.

Inevitably talk of prior relationships will come up. 

When that happens, it’s important to keep things positive, to take responsibility where you can, and to demonstrate what you’ve learned as a result.

When a man blames and doesn’t take responsibility for their own part in a relationship, it’s a sign that history will repeat itself. It’s also likely that they aren’t aware of their own toxic behaviors and thus, aren’t working to improve themselves. It also shows a general lack of awareness – that ain’t cute.

A man who takes responsibility is humble, sexy, and total boyfriend material.

When You’re A Man In Your 40s Or Older

You are staring at a woman across the table who is your equal. She has experienced many of the same social, financial, and relationship obstacles that you too have encountered. The pair of you grew up during the same decade, watched the same shows, and consumed the same culture. Dating someone your same age shouldn’t feel odd, it’s something you’ve been doing most of your life.

A woman that shares the same culture and has had the same experience as you will make for a great romantic companion.

What’s Her Attachment Style

Most likely the woman you’re dating has had healthy relationships in the past and is single because she’s divorced or simply has never found someone worth settling down with. While this is the likely scenario, it might not be. It’s possible that she has attachment issues that have never been resolved.

Find out what type of attachment style she has. Her attachment style can be discovered by learning about her dating history and monitoring her behavior around you. If she’s erratic and only touches base with you once a week, you can likely assume that she has an avoidant attachment style. Figure out her attachment style before you spend too much time in a relationship that’s going nowhere.

Don’t Stop Taking Care of Yourself – What 40-year-old Women Want

Women in their 40’s have a hard time finding quality prospects.

This is the primary reason many of them aren’t in fact looking to date.

Dating 40 year old women

There are many things that women in their 40s can’t find in a partner – a toned figure is one of them.

The more you take care of yourself, the more desirable you will be to women in their 40’s – that’s how it’s always worked.

If you’ve stopped working out for whatever reason, hire a trainer, or sign up for a 10k or 1/2 marathon to get yourself to commit to a regular workout schedule and to hold yourself accountable.

If you haven’t bought nice clothes for yourself in years, hire a professional stylist or join my coaching program and work with our celebrity stylist, Hailey to get a dialed-in wardrobe that you’ll feel confident, handsome, and sophisticated in.

Wear a nice cologne. Women love a good scent, make sure you have a signature scent that you wear regularly to get women you date into their senses and out of their logical minds. Dating is all about sensation and emotion, not about logic. Bringing her into her senses with a good cologne is a great start towards escalating sexual tension.

Look good, feel good, date good.

What 40-year-old Women Want – A Man That Isn’t Desperate 

If you’ve ever been told by a woman or friends or family that you’re needy or clingy, chances are you have an anxious attachment style.

You can take a free attachment style quiz online to learn more about your style. Should you want a more in-depth understanding read the book Attached.

If you self-identify as a man who falls in love really quickly. If you’ve ever scared a woman away with intense energy, then MegaDating is the important solution I highly encourage you to use.

In my coaching program, I set the goal with my clients of going on 20 dates in 90 days and really committing to doing that before they get involved in an exclusive relationship with anyone.

As I said before, MegaDating is the process of dating multiple women in a low-stakes environment quickly so you can diffuse your energy, increase your confidence, and protect yourself from getting too focused on any single woman too soon.

It will change your whole life if you commit to it.

I know, I’ve been in your shoes.

Before my 100 date experiment, I pushed a lot of guys away because I wanted to jump into a relationship with them super quickly.

But when you MegaDate, you gain control over your romantic life and you don’t act desperate or clingy because you have too many different people you’re meeting that your energy diffuses. 

MegaDate (Don’t Play Games)

MegaDating is a dating technique you can use to date a myriad of women in a brief period of time, thus accelerating your search for a long-term partner.

how to stop pleasing people

In my coaching program, I teach my clients how to fill up their dating funnel using dating apps and in-person social strategies so they can go on 1-2 dates per week.

This helps to fill up your social calendar so you’re not overly available and lose a woman’s interest that you’re dating.

Another benefit of MegaDating is that it does away with any fears of scarcity you might have. 

When there is an abundance of women out there you’ll quickly learn you don’t have to settle on the first one that’s into you.

This is of vital importance.

Especially if you’ve found yourself dating women in the past who you weren’t particularly excited by but you felt sort of stuck with.

MegaDating really allows you to take your time and find a woman who’s right for you. If you’d like to learn more about how my coaching program can help you MegaDate your way to your dream relationship, book a new client session with myself or a member of my team here.

How To Date A Woman In Her 40s: Consolidation Of Lives

How do you go about combining your families? If you both already have kids, houses, financial assets, and social circles how do you go about integrating your lives? It was a lot easier in your 20s when you weren’t already a paramount part of a social ecosystem. By dating a woman that already laid her roots down, you’ll have to work to assimilate into each other’s lives.

Changing Habits

It’s easier to grow with someone when they’re young and more malleable in their ways of living. But as a 40-something the woman you’re dating is already set in her ways. To make the relationship work you’ll have to accept her for the person she is. Don’t expect her to take up scuba diving or stop watching The Bachelor just because she’s now dating you. Her habits were there long before you came around and they’ll most likely stick around for the rest of her life.

Long-Term Benefits

Dating a woman in her 40s means greater stability. She is more likely than her younger counterparts to be able to offer you lifelong companionship, financial security, an extended social circle, and more. A 40-something is much less fickle than a 20-something. You know what you’re getting when you start dating a woman your age.

Final Thoughts

Just because she’s in her 40s doesn’t mean that she wants to be treated differently than a younger woman. Be chivalrous, surprise her, take care of her, make her feel respected, worthy, and sexy.

Also don’t be surprised if she has to reschedule an outing because of family or work reasons. You’re walking into a woman’s life who already has an established professional and family life. As such, you may not always be the top priority.

Still have questions about dating women in their 40s? Book a new client intro session with me to talk about any burning questions you might have regarding dating a woman in her 40s. During our session we’ll discuss your dating history, the obstacles holding you back from achieving your dating goals, and see if my coaching program can help you reach your dating goals!

Comments are closed for this article!

Featured Articles