7 Things Cis Men Over 50 Need to Remember When Dating Women

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7 Things Cis Men Over 50 Need to Remember When Dating Women

More and more, people over 50 are dating every year. We are still having sex, falling in love, and working out relationships with each other

People, like myself, born in the 1950’s and early 1960’s were raised with some heavy patriarchal programming, and yet by the late 60’s and 70’s, the women’s liberation and gay rights movements began to dismantle that programming.

However, the culture one is born into and experiences as a young child in, can leave a lingering imprint — and my generation still retains some of those old ideas.

Especially the straight, cisgender, white men who still retain so much power over what is and isn’t socially acceptable.

And as a woman who predominately dates straight, cisgender men, so far, I notice that these old ideas pop up more commonly, or at least more overtly, for people in my age group than they do for women 30 years younger than me.

For example, one of the biggest areas of programming is the misogynistic idea that a woman’s appearance is her defining power, and that women must compete against each other in a sort-of underlying appearance competition.

While this idea unfortunately remains in TV programs, music videos, print and media advertisements, and so on till this day, I often feel like women my age struggle with this more than the younger women I know because the culture promoted this competition more fiercely when I was young.

I have lost count of how many times I heard the question, “Any competition?” or “Are there any other girls at school after him?”, upon expressing interest in a boy during my youth. Girls were programmed to try desperately to be the most attractive girl around; we were taught that this made us more desirable to men, supposedly, and thus to society. 

In addition, the very concept of what was attractive was also drilled into our young brains, and unfortunately, what was considered attractive was informed by racism, ableism, ageism, and cis-gendered heterosexuality.

Even more unfortunate, the competition increased as girls became women. I entered college in the fall of 1975 and graduated spring of 1980. During that time, although I no longer felt pressured to solely care about appearance and dating, meeting a man to marry was still just as expected as finishing college and finding a career.

I cannot begin to tell you how many times over the past 3 decades, since my late 20’s, I received looks that mixed confusion and pity as someone asked me, “How come a great woman like you is not married?  Then when I was married, it was, “Why don’t you have any children?” 

This value system is archaic and it saddens me that so many men still carry this expectation of women in my generation.

I believe actually stems way back to the prevailing attitudes during Medieval times, which instilled in every woman that her sacred duty was to be obedient to her husband and bear children.

It does not serve anyone to cling to tired old misogynistic patriarchal patterns, and dating later in life is a great time free yourself from those old patterns. Being married and with children is wonderful, but it is not a requirement in order to be a “real woman” — an expectation I grew up hearing and still occasionally encounter from the men in my life.

I don’t mean to imply that you should date for the sake of healing misogyny, but rather dating for no other immediate reason than to simply enjoy someone’s company is, in and of itself, an act of liberation. 

It is fine to also date hoping to marry or remarry, but my point is to not make that the focal point of dating, right away. People in their 50’s have been through so much more loss, death, birth, career changes, and so on, that I have noticed the over-50 set is positioned perfectly to enjoy every moment that comes their way, when possible. 

Many people over 50 finally are more present in their lives, perhaps because they really understand how none of us know how long we will be on this beautiful spinning world. Dating can be a way to revel in the moment; I encourage it to be viewed that way, at least initially.

So, if you are a straight, cis man over 50 interested in dating women, here are some critical feminist don’ts for you. And since I am mostly heterosexual and know it more thoroughly than queerness, I will focus on that type of dating here.

1. Don’t Assume The Woman Dating You Only Dates Heterosexual Cisgender Men — Even If That Is What You Are. Don’t Assume She Is Cisgender.

The idea that your date is straight, cisgender, and dates the same is informed by heteronormative and cisgender-normative values. It is what we were raised with.

I get it.

But those messages were deeply sexist, erasing, and validated a lot of violence against women and non-binary people. It is time to let them go! 

To help you let it go, just refer to the Bob Dylan lyrics, “The Times, They Are A Changin’.” Then, just enjoy being with her, without rigid expectations about who she is and how she dates.

Rather than project outdated, oppressive and very boring rules on her, embrace the beauty of a woman telling you exactly who she is and how she would like to be treated. Besides, who knows what sort of new, unexpected things you might learn about yourself and your own desire.

2. Don’t Perpetuate A Double-Standard Around Age and Gender 

No, you don’t “have to date a woman 20 years younger because women my age only want to sit on a cruise ship and talk.” Yes, I really was told that, when approached by a man much older than me.

This attitude that women should be younger than the man they are with, alongside being ableist, ageist, and fatphobic, is rooted in the underlying assumption still lingering for men my age that part of the reason why women are here on earth is for a man’s pleasure — so she needs to fit into his standards of desirability. 

This attitude also has an underlying assumption that much younger women are more desirable, and therefore the man feels, since he is entitled, that he must be with a much younger woman.   

I distinctly remember, even as a girl, assuming I would marry an older man, since media and TV was saturated with those images.

This was instilled in girls of my generation, as soon as we could comprehend the idea of marriage.

Whatever you are doing, a woman your age can do it just as well. And you don’t have any right to criticize, ridicule, or discard any one who can’t do it. We all age, and as we age our bodies and desires change.

I applaud a woman who pursues her own sense of joy — be that on a cruise ship, at the bingo night, or climbing a mountain.

Further, if a woman has made it known, for instance, that she wants to  date a man 7 years younger to 7 years older, she has done that for a reason.

Personally, I ask for that simply because I really enjoy shared generational experiences. That matters to me.  So when a man 20 years older approaches me with a sense of entitlement and expectation that I do the opposite of what I set out to do, simply to please his appearance expectations, I find that irritating and invalidating to older women.

I find myself wondering why he is not enjoying a wonderful woman closer to his age.  And why he is not respecting what I have specified, almost like what I spell out is of absolutely no merit, and can be ignored.

3. Don’t Perpetuate the Misogynistic Pattern Of “Body Competition” Between Women 

As I mentioned in the introduction, women my age were brought up thinking they had to compete for male attention in an appearance contest. Please don’t perpetuate that.

I have had men tell me that although I did not have big boobs, I did have long legs, and they preferred that anyway. Uh, no.

Telling me that is insulting me and all women. 

Don’t compare and contrast our appearance. Please be prepared to learn that most women over 50 are fairly secure in themselves and are able to appreciate beauty in its many many different human forms. 

How about we enjoy noticing beautiful people around us, together, as well as beautiful dogs, cats, trees, and clouds! That is much more interesting than perpetuating misogynistic body part contests.

4. Don’t Assume We Are Monogamous

We might not be. And don’t make blanket assumptions about us if we are choosing to follow a loving, caring, ethical polyamorous lifestyle.

Similarly, don’t make negative assumptions about us if we prefer monogamy!

Certainly go ahead and bring up those lifestyle choices. Perhaps not immediately. We may want to discuss shared interests, politics, spirituality, and other topics, before diving into intimacy discussions.

5. Don’t Assume That Our Genitals No Longer Work

I bring this up because that myth STILL comes up. Sadly, even young women have implied such misconceptions to me, which especially hurts to hear.

That prevailing assumption about women over 50 is informed by entrenched youth privilege in this country, as well as misogyny, and internalized misogyny.   

The flip side of that is similar to the slut-shaming that sexually active younger women can face.

An older man who flirts is usually validated as being youthful and vibrant, while an older woman who flirts runs the risk of being told she is “desperate.” 

Yes, I received that comment after some harmless flirting, some reciprocal flirting, I might add!

The underlying message is how dare an older woman be sexual —  well, uh, I am daring, and so are plenty of other women my age.

Most sexual women over 50 are practicing whatever genital self-care works for them, so they can enjoy, really enjoy, many years of sexual activity.  Men over 50 can also practice self-care for their genital area. We will work with you. 

If you take Viagra, or a more natural equivalent, do not think we will think any less of you. Age happens. It is not something to hide in horror about; just do something about it.

If you need to pause for 15 more minutes of foreplay so the blue pill will kick in, do you really think we are going to mind?

No, we will enjoy those 15 minutes, so much!!!! 

And, one is never too old to buy some books, go online, and/or take some fun classes on sexual pleasure.

If you’re in a sexual relationship and your partner consents, feel free to try out your new advanced sexual education!

6. Don’t Assume a Smooth or Specific Trajectory with Our Dating Relationship

We are both in a different phase of life than when we may have dated before. Just because we have been going out every Friday night, don’t assume we lose interest if we are unavailable for a month or two.

We may have a parent who is dying, or a close friend who is sick; we may need to take off for 2 months to be with them. The same thing may happen to you, and we will not bail on you, or make any negative assumptions. 

How about you send us cheerful emails while we are away, or call us, and even ask if there is anything you can do while we support our loved ones in their time of need?

Many of us also have reached a pinnacle in our careers, and all of a sudden may be engrossed in the project of a lifetime. We still value you, we may even treasure you, but we want to achieve this very important goal.

Be understanding about our periodic lack of time; show excitement and support for our achievements.  There will be other times when we are much more available. 

7. Don’t Be in a Rush to Give Us a Label, or Specifically Define the Relationship

Many of us just want to enjoy your company, and have no agenda. Again, most women over 50 have a secure sense of themselves.   

It is not that we are ruling out a serious long-term relationship — it is that we often do not have that as a clearly defined goal.

How about we enjoy each other, and this big beautiful world we live in!  If we end up having a long-term relationship and/or marriage late in life, great!  But it is a relief for many women over 50 to not have any specific relationship goal, but to just enjoy every moment with our new-found friend. 

What enjoyment looks like to each person is different, and can be discussed and explored as time moves on.


This list is by no means definitive, or will it resonate with every woman over 50 who is dating.  But I hope it is a start.

I will close by saying I have enjoyed and still enjoy getting to know men at this stage of my life. I still am attracted to them, and I still want to get to know them. 

I also enjoy the fluidity of having no specific partnership goal in mind — except to simply enjoy my romantic connections and to let them enrich my life.

I have recently undergone a big relocation, and as I settle into my new home, I am starting to meet and enjoy conversations with local men. 

I don’t doubt that I will date soon enough — hopefully incredible feminist people who value love and happiness more than the status quo — and I look forward to it!

This article was written by Amy Ballard Rich on Everyday Feminism