Why It’s Hard to Date Women Over 40

We know who we are and we know our worth

There’s something I’ve learned about myself in my forties: It is very hard for men to date me. To fall for me. To love me.

You see, I’m no longer the desperate young woman of my past who was hoping to fast-track her dreams of becoming a young wife and mother. I’m also no longer the desperate almost-middle-aged woman trying to find her “last minute life partner” so she can pop out a baby before it’s too late.

It is too late, guys. The days of young wife and mother are looong gone. The days of squeezing in a geriatric pregnancy are over.

And here’s the big problem: I’m happy with myself and my life. I have made peace with the way it has unfolded. I’m not desperately hoping for a last-minute intervention, or desperately searching for something to fill a hole in my heart from my youth.

To put it more simply: I’m not desperate.

Not being desperate, I’ve found, is super inconvenient for what seems to be a large number of men on the dating market. Everyone says desperate women are exceedingly unattractive, but that’s a myth, so far as I can see.

My experience has been that self-possessed women who don’t feel a pressing need to change the circumstances of their lives are the ones who these men find hard to date.

You see, a woman like me knows what she is looking for when it comes to dating. I might not have all the details worked out — for instance, I don’t know what kind of “container” I want (marriage, monogamous partnership, deeply connected lover, etc.), but I know exactly what I want to put into the container.

Whether it’s with a man or a woman or anything beyond or in between, I want intellectual and creative stimulation. I want mental, emotional, and spiritual sparks. I want someone who opens my mind and soul. I want someone who will go as deep into the boundless depths of the universe as we are both willing to go.

I want someone who is overflowing with sexual energy and who wants to use that energy in creative and unusual ways. Someone who is hungry to use their sexual energy as a portal to greater understandings of self, of other, of love, of the world.

I want someone who will argue with me. Who will challenge me and demand my accountability. Who will take my challenges seriously and remain committed to their own accountability.

I want someone who will see me as a treasure. Not something to covet, but something to cherish for as long as we are given time together. Someone who will hold, love, and protect my heart above all.

That might be a long list, but really, it’s quite simple to me. I know what I want.

But that’s only half the story.

There are two ingredients in the making of a woman who is difficult to date. One is her knowledge of herself and her desires. (Check.)

The second is that she knows her worth.

Women in this culture are sent into the dating pool at a great disadvantage. We are taught, over and over and over again, to undervalue ourselves. In the workplace. In friendships. And most especially in romantic relationships.

We’re taught that our expectations are too high. We want too much. We’re made to believe that vocalizing our standards makes us “nags” and “harpies.” We’re too emotional. We’re irrational and illogical. Our perspectives and reactions have to be tempered by the acknowledgement of our…you know…periods. (And you know how I feel about that.)

We are regularly undermined and gaslit when it comes to romantic relationships — and that happens even with a partner who has the best of intentions, and even within ourselves. Yes, we are taught to undermine and gaslight ourselves.

We’ve seen our mothers settle for relationships that leave them feeling empty and unfulfilled. We’ve seen aunts and grandmothers silently look away when their husbands stepped out with another woman, dutifully enduring that pain and humiliation. We’ve been taught how to behave in order to be a “good wife.” We’ve been taught that the emotional labor of a romantic relationship falls to our responsibility. And, perhaps most heinously, we’ve been taught that it’s okay to build a relationship with someone who is fundamentally wrong for us…because it’s our job to help him grow into a better person, right?

Over time, a woman starts to focus on getting to know her soul, instead of looking for her soulmate. And when that happens, major shifts begin to happen. She suddenly realizes she isn’t okay with enduring silent betrayals. She isn’t okay with a barely satisfying partnership. She doesn’t want to fold all the laundry, cook all the meals, and carry both her own and her partner’s emotional weight.

And most of all, she realizes she isn’t here to fix anyone — nor are male partners broken in the first place.

With this comes a new understanding of herself and her worth in the world. She realizes what she brings to a partnership. She realizes that the messages of her inherent unworthiness were all wrong from the very beginning.

She’s Sleeping Beauty — except she doesn’t need a prince to wake her with a kiss. She learns how to wake up all on her own, look around that dusty old tower, and say, “Fuck this. I’m gonna go back to my cottage in the woods and have a glass of wine.”

My forties have brought me clarity on these two issues. I know what I want in a partnership and I know my own worth. I’m no longer willing to compromise on what I want and settle for a lukewarm love that positions me (the woman) as secondary. And I’m no longer willing to let a partner convince me that I don’t deserve their love and respect.

My experience has been that many men don’t like this. I’m the woman, after all. I’m supposed to smile and wait patiently when a man suddenly stops texting or calling for days or weeks at a time until he’s ready to re-prioritize me. I’m supposed to remain silent when a boundary has been breached and not inconvenience him by bringing the violation to his attention. I’m supposed to fit my schedule around his work and family obligations. I’m supposed to laugh when he teases me about being overly emotional and to diminish my own accomplishments because my work is just art.

In other words, I’m supposed to make him feel good and make his life easier without having any such expectation of him doing that for me.

And when I refuse this script, things shift dramatically. They withhold their attention from me. They retreat. They stop freely sharing important information. And eventually, they tell me they lost their feelings for me and that they can’t move forward any longer.

I know they are annoyed with me. I know they think I’m haughty and unreasonable. I know they’re punishing me for stepping out of line.

I’m 45, childless, and never been married. They thought I would be desperate. Desperate enough to do whatever it took to keep their attention.

But they got me all wrong.

I know what I want and I know who I am. If my online dating profile was still active, that’s what I’d put at the top. Maybe that would scare away the type of men who would mistake me as an easy-to-manipulate desperate woman who would put up with any old shit.

You see, I won’t sit around for hours waiting for a man to get off a business call when we had already made other plans. I’m not going to put up with a man teasing me about my work or my emotional depth. And I most definitely will not tolerate lies or a suspicious lack of transparency.

When I put these boundaries down, the guys in question react with shock or anger. Apparently, I’m supposed to feel lucky to have their attention. I’m supposed to be willing to put up with whatever they have to hand out.

But sorry, guys, I know what a fucking amazing partner I am. I know how much I bring to the table.

I am a diamond and I will not allow men to treat me like some random sedimentary rock.

I’m not afraid to say goodbye. It might hurt for a moment if my feelings got involved, but believe me, I’d rather be alone than settle for someone who can’t offer me what I’m looking for and who treats me poorly.

Instead of changing, instead of begging, instead of settling, I’ll instead walk him to the door (or walk with him to the door if he’s already leaving) and see him out with a smile. I have things to do, after all, and can’t afford to be distracted by cheap performances.

I want the real deal or nothing at all.

And a woman like that is, indeed, the hardest kind to date.

There is nothing a relationship holds for me that would be worth giving up my needs and my sense of my worth at this point in my life. Perhaps Jane Eyre said it best:

“I can live alone, if self-respect, and circumstances require me so to do. I need not sell my soul to buy bliss. I have an inward treasure born with me, which can keep me alive if all extraneous delights should be withheld, or offered only at a price I cannot afford to give.”

© Yael Wolfe 2021

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