Dating Older Women: Everything You Need To Know


A casual walk down the street nowadays reveals an interesting sight: young guys walking arm-in-arm with older women. There are many reasons for this trend that, while already present since the dawn of time, is experiencing a renaissance in our modern world.

Maybe it’s the excitement associated with seducing a member of the previous generation. Maybe it’s the thrill involved in flaunting a dating lifestyle that is still generally considered a mild taboo in social settings. Or maybe it’s just love regardless of the difference in birthdates.

Whatever the case, dating a woman your senior has its own difficulties compared to dating someone your age, and if you’re not prepared to face these challenges head-on, your boundary-breaking romance might not materialize the way you wanted it to.

Why should I look for older women?

All things aside, dating isn’t really a conscious choice but an instinctual response. You can’t decide who you are attracted to; it just naturally happens. If you’re a young man who finds that older women turn your crank much more than the young gals, then your problem isn’t really related to preference but to the perceived benefits and costs. The unique challenges will be discussed below, but here are some of the advantages of dating a member of the past generation:


These older women will have a certain sense of character that comes naturally with age and experience. They know how to balance a checkbook and take care of the household. Gone are the days of partying all night and waking up face down in a pool of vomit. If you want someone who has her sights straight and knows how to be responsible, then dating up is the right choice.


This applies not just to sexual matters but life in general. A woman of advanced age has been through many things. She is more than capable of taking you under her wing and teaching you something new. Although it’s not a good idea to overdo it lest you become needy, soaking in the wisdom from a more mature individual is apt to get you a head start in life even if you two don’t end up as a couple.


Most older women already have a stable career and money in the bank. If you’re just starting work, she may let you crash in her apartment to save cash or even give you some crucial social contacts. Of course, just like everything else, don’t turn into a parasite; a woman whose seen and done it all is not going to take any attitude from a young punk who decides to use her as his sugar mommy.

Are older women really looking for younger men?

It depends. Although it certainly isn’t the norm for older women, there is a sizable population out there who are specifically looking to date someone their junior. Many reasons abound. For some middle-aged older women, anxiety about growing old without a partner spurs them to take into consideration men outside their own generational bracket.

Others might be flattered at the fact that a younger, more virile man is even interested in them in the first place. A few might just be in it for the sexual kicks, and these older women are often termed cougars or MILFs.

Overall, the vast majority of these older women are nearing there menopausal period and are searching for genuine relationships that would lead to children, not one-night stands. Do not make the mistake of classifying every senior female as a deprived, sex-hungry homemaker (chances are, she has had more sexual experiences than you have).

If you are simply looking for a good time, then it’s best not to lead them on to false promises. On the other hand, if you also want to settle down, then she might be the best thing that ever happened to you.

How old is too old?

There is still such a thing as cultural norms though, so despite the fact that inter-generational dating is becoming more acceptable, you may need to put some boundaries on yourself if you want to avoid the disapproval of your family and friends.

A good rule of thumb is the “twice your age minus fourteen” rule. This calculates the upper age limit of the woman you’re allowed to date. For example, applying the rule to a 29-year old man would yield the number 44 (29 times 2 minus 14), which means that he can safely date anyone up to 44-years old without drawing any public attention. Going beyond that would be too risky and may lead to ostracization.

A more scientific approach would be to stick to your own psychological stage of life. The psychologist Erik Erikson developed his levels of development as follows:

  • Adolescent (age 12-18) – focused on identity issues
  • Young adulthood (age 19-39) – focused on intimacy issues
  • Middle adulthood (age 40-64) – focused on generativity
  • Older adulthood (age 65 and up) – focused on ego integrity

According to these levels, it would be unwise to date someone outside your range of development. For example, an 18-year old dating a 50-year old would have a lot of problems to deal with, because the teenager is likely to obsess on “finding himself”, while the middle-aged woman is more concerned with leaving a legacy for the next generation.

They might find some common ground in sexual intercourse, but a relationship built on nothing but bedroom antics is sure to fail long term. However, it would be perfectly fine for a 25-year old to date a 35-year old, since both of them are focused on the same task of finding intimacy.

At the end of the day though, it’s all up to you to decide. These are merely guidelines, not rules. Let your heart and your brain talk amongst themselves and then go for the option that you think would lead to your happiness.

Famous couples with large age gaps

Here is a list of couples wherein the woman is much older than the man:

  • Halle Berry and Gabriel Aubry (9 years)
  • Mariah Carey and Nick Cannon (11 years)
  • Susan Sarandon and Tim Robbins (12 years)
  • Deborra-Lee Furness and Hugh Jackman (13 years)
  • Mira Sorvino and Christopher Backus (14 years)
  • Demi Moore and Ashton Kutcher (15 years)
  • Tina Turner and Erwin Bach (17 years)
  • Sam Taylor-Wood and Aaron Johnson (23 years)
  • Madonna and Jesus Luz (28 years)
  • Joan Collins & Percy Gibson (32 years)

Principles For Dating Older Women

Before we talk about what to expect when dating an older woman, please note that all older women are the same. This means that the attraction mechanism that works for one girl will work for another, regardless of age. If you’re looking for a general guide on how to get a girlfriend, this comprehensive article will clue you in to the whole process. The section below is merely concerned with the unique aspects of dating this particular type of female.


A woman in her mid-forties has experienced much heartache and triumph in life. She has struggled through hard times and made a name for herself with little to no help. Therefore, she does not have time for any fake sympathy that a younger woman might give. For example, if you are fired from your job, a younger woman might allow you to cry on her shoulder and mope around the house for a few days. Older women, however, will find this kind of behavior irritating. By this stage, they are looking for a stable partner, not another child to coddle. If you want to keep her, you need to do the following things:

  • Make sure you have a career. Slackers who hop from one dead-end job to another can bet that the woman will drop them faster than a sack of burning leaves. You might be able to seduce her based on raw animal instinct alone, but seduction is fleeting. The moment she realizes that you don’t have anything else going for you other than your testosterone is the moment she’s going to reconsider her options.
  • Keep your insecurities to yourself. This applies to all women, but especially to older women. Showing insecurities is the mark of an adolescent, and while most young girls are forgiving about this behavior since they themselves are doing it, a forty-something will be less tolerant. Therefore, do not try to express your deepest hurts and pains unless it’s a matter of life and death. This just shows that you’re begging for attention, a decidedly unattractive trait.
  • Solve your own problems before seeking aid. Whenever something comes up, try to work on it first before asking her help. Demonstrating initiative like this is the trademark of a mature man and will certainly show your partner that she’s picked someone independent. Even if you end up having to ask for her help, chipping away at things that you can do on your own will go a long way towards proving that you’re not just another mouth to feed.
  • Have a life outside of your relationship. Women want to follow you on your journey. They want to ride shotgun while the man takes the wheel. Most younger women crave excess attention from their lovers, but older women get turned off by clinginess. If you do not have any hobbies outside your relationship and spend all your time with her, your partner will find out that you’re not fit for any long-term goals and will quickly abandon you for someone else who has a more focused lifestyle.


Let’s face it: no matter how psychologically mature you are for your age, you will never reach the same level as a older women ten or twenty years older. There will be plenty of times during your dates when you will come across as a childish moron. There is no way to prevent any of this from happening; you’ll just have to chalk it up as one of the consequences of dating someone your senior.

However, while she may have the advantage in terms of character development, you clearly have the upper hand when it comes to youthful exuberance. Older women just cannot keep up the same adventurous pace that they demonstrated during their twenties.

A man her age is also crippled in this manner. You, however, have abundant amounts of energy that you can give away free. The best way to compensate for the disadvantage of being young is through the advantage of being young.

Make your date feel like she’s a teenager again by infecting her with the excitement that comes natural to you. Do not take things slow during your dates – candlelit dinners, romantic movies, etc. – because these are the activities that she is already accustomed to.

Rather, use your creativity and go for more adrenaline-fueled pastimes. For example, a fast run in the rain is better than a slow walk on the beach. Not only will she be forced to keep up, but she’ll reclaim the lost passion that she had during her youth.

This applies even more so in bed. A senior woman will want to be ravished by a youthful conqueror, so go at it like you’ve never gone before. Take the lead and let her know that you’re considering ripping her clothes off with your bare hands. Nothing is as revitalizing.

Of course, this doesn’t mean that you can’t take breaks. She may not let you know that she’s tired, so pay attention if she’s getting uncomfortable. Being considerate as well as being energetic is a surefire way to keep her for good.


An older woman is already self-conscious that she’s dating a younger man, but you’ll make her feel even more insecure if you point out the fact that there’s a significant age gap between the two of you. The embarrassment you potentially experience when introducing her in public to your friends or family is nothing compared to the discomfort she feels when walking around with a guy who is young enough to be her son, especially nowadays when people are quick to label her as a cougar or MILF. You can make things easier by pretending there’s no age gap.

This does not mean that the subject cannot be discussed. What this means is that you are obliged not to make a big deal out of it. If she expresses concern about other people’s negative opinions, show genuine indifference towards it. The more comfortable you are about your relationship, the more comfortable she is too.

Let’s face it: it takes courage to walk around with someone from outside your generation. Most guys would try to hide their faces. Accepting the reality without judgment is a great way that you can attract her with minimal effort. She’s going to appreciate the gesture.


While everyone’s physical appearance deteriorates as they age, women will feel more anxious than men because of higher societal expectations. This is the reason why plastic surgery is more common among women; they all want to achieve the impossible cultural standards of beauty.

You may be tempted to joke about wrinkles, sagging breasts, neck folds, and any of the like, but your partner will not take it lightly. Even if this is done in an entertaining manner, it’s better not to talk about her body in general unless you have a compliment.

On the other hand, the woman herself might complain about her physical appearance. In this case, you must tread carefully. Any attempts at telling her that she looks just like a teenager will be taken as a bold-faced lie. On the other hand, she also does not want to be told the truth; she already knows she’s getting old.

What she wants is simply your reassurance that despite her inability to maintain her fleeting looks, you still find her beautiful and won’t dump her for the sorority chick at the nearby community college.


The fifth principle of dating older women is to meet her halfway when it comes to satisfying both your needs. For example, a mid-twenties guy will often want to go out clubbing and partying all night, whereas a forty-something woman will be too tired by eight PM and would rather stay at home. This can be the deal breaker for some dating couples.

The only way to solve this problem of irreconcilable goods is to meet her halfway. Both of you might decide to go clubbing this week for your sake, and stay in for the night next week for her sake. Alternatively, you can combine both activities and have a small, private party at your own house – a smooth compromise that allows both people to enjoy themselves.

This is the major downside of dating someone with a large age gap, and the larger the gap, the more difficult it is to come up with a plan that appeals to both individuals. It’s always a good idea to follow either of the two guidelines given above when picking a woman from outside your own generation. You do not want to overextend too much.


Finally, realize that a woman this old who is still single probably has a few skeletons in the closet. She may be previously divorced. She may already have kids. She may still be married and is using you for an affair. She may have been a hard-driving careerist who put work first before family and relationships. She may be desperate to have children before her biological clock runs out.

None of these may ring true for the woman you’ve chosen, but it’s good to be aware. For example, there are documented cases of middle-aged older women nearing menopause who deliberately lie about being “safe” in order to trick a man into getting her pregnant. Some even go too far and steal semen from a used condom. Do not let these horror stories put you off, but rather to remind you that older women are not perfect just because they are more mature. They still have fangs just like everyone else.


Dating older women definitely has its advantages and disadvantages. If you’ve always found yourself going out with someone your age and wondered what it’s like to broaden your horizon, then you may want to consider spending time with an older generation of girls. They’re just as vivacious and loving as the ones you’re used to, maybe even more so. Who knows, you may even find your special someone. Do not let this opportunity go by.

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