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How To Date A Woman In Her 40s

By Emyli LovzMay 27, 2019Strategy
how to date a woman in her 40's

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 Hitting on women in bars feels outdated and forced during a time when men and women are less social than ever.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.


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 child bearing years behind her, she’s physically less in shape than a woman in her 20s, and has less 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?

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?

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 your new girlfriend 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 rightly 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.

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 American Idol just because she’s now dating you. Her habits were there long before you came around and they’ll most likely to stick around for the rest of her life.

Long-Term Benefits

Dating a woman in her 40s means that you won’t be lonely again. She can offer you lifelong companionship, financial stability, 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 drastically different 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. You may not always be the priority, get used to it.

Still have some questions about dating women in their 40s? Book a 1-on-1 New Client Skype session with me to talk about any burning questions you might have regarding dating a woman in her 40s. During our session we’ll also diagnose your dating history, co-create an action plan, and see if my 3-month coaching program could help you reach all of your current dating goals!