Dating After 50

I’ve only been looking into this whole dating after 50 thing for about two months. Apparently, the rules have changed. To me though, the rules are the same. I’m still looking for men my age, so for them, the rules are pretty much the same.

This is not good news.


I’ve only been looking into this whole dating after 50 thing for about two months. Apparently, the rules have changed. To me though, the rules are the same. I’m still looking for men my age, so for them, the rules are pretty much the same.

This is not good news.

No matter what they all say, the rules are the same. It seems, to my poor addled menopausal brain, that there are even more rules now.

Granted, they appear to be the same rules as when I was 20, but somehow they are a bit skewed when you are approaching them with a belly full of living through all the crap you have lived through in the intervening 30 years.

I am not looking for a man to rope into marriage. I would just like to find someone with similar interests who wants to hang out now and then.

And I would prefer to find just one.

I know! I set pretty high expectations for myself. Hey, if I found one once upon a time, I can find one again.

Surely men hate this dating crap too? Maybe not (see Advice from High School Sweetheart below). I am finding it exhausting.

First Date

The first problem a woman over 50 faces (or any age I suppose…I am recalling my teenage years) is getting a man to ask you out in the first place. At our age, none of us knows who is married or not, so how do you even know if the one you are attracted to is unattached. Risky business that. Not all men wear their wedding ring. I suppose not all women do either.

I’m told to circulate, get involved in activities, go online to a dating site. I suppose these are valid choices, but I don’t see myself doing them. Who has the time?

Help me out here, friends! Because I have no clue how to get that first date. I have done the approaching. I have asked a man out. But these older men seem wary of that technique. Whoever said you can’t teach an old dog new tricks is on to something.


Advice from your best friend Because let’s face it, she is the first one you are going to ask for help. This advice is for after you have gotten that first date and decided you would like more dates with a particular man.

“You have to train him.”

This brings to mind training a dog – an image that I am not all that pleased with. Apparently, men are rather stupid (my brother says they are stupid because women are crazy).

At any rate, yeah, men are not the best communicators when it comes to women, so it is necessary to ‘train’ them. So. Yeah. There’s that.

I’m not going there either. If I have to train you, I don’t want you. I already raised my kids and trained my dogs. And I wasn’t very good at training my dogs, so I doubt I would have much more success with a man.

Advice from other women friends “Make him chase you.”

Do you understand how old I am? I really don’t think any of you understand how old I am. I feel a tremendous need to remind you how old I am.

Who has time for this dance, this ritual, this prehistoric game of king tag? I am 54. Repeat. Fifty. Four.

Every minute another wrinkle inches it way across various body parts. Things are sagging in places I had no idea were capable of sagging.

I am running out of time here, people. Still. The chase, the game. Men are still guys, no matter how old they get. They have to conquer. They enjoy the sport.

They want to win, defeat, bring that doe down.

Advice from your brother “Relax.” What did I expect from him? Sigh….

Advice from your son  “Don’t act needy.” Seriously?

Guys have it all wrong if they think I am being ‘needy.’ I simply know what I want. I don’t understand their need to play a game first. Can’t they just go watch some sports if they want to participate in a game?

I do not need a man to validate me. I do not need a man. I want a man. I still have the same biological urges as the rest of you. No time for games; the wrinkles are winning.

Advice from your high school sweetheart “Men just want to have a drink and get laid.” I say this nicely. His words were a bit more, shall we say, sewery.

I find this advice somewhat reassuring. At least I am familiar with this one – men are pigs. I’m not being mean! They’ll tell you that themselves!

Advice from a Female Dating Coach “Men are motivated by wanting to keep you safe and protected as your hero.”

Seriously? Still? This is sad news for a diehard feminist. I have spent 30 plus years working on proving that I can do everything a man can do, quite possibly better in some cases.

And now you are telling me I have to let a man save me? I would like to point out that this is the opposite of Advice from your son.

On the flip side, I will admit that I felt a thrill when the man I went out with stepped around me on the sidewalk so that he was near the road, not me. Naturally did this. Without breaking stride. Yeah, that was really nice. And yes, it made me feel ‘safe and protected.’

So, maybe my brother is right…women are crazy.

Advice from a Male Dating Coach “Let him ask you out, contact you again for the next date and be the pursuer.”

Oh dear God, what century do we live in??

I have been accused of being too fast, too pushy. If I was 20 or 30 or 40, I would agree. But I’m pushing 55 and I just don’t have the time or energy to sit on a fence or ‘play the field.’

Final Analysis

I am exhausted from trying to figure men out.

Seriously, I’m thinking perhaps I would rather be alone with my dogs. They may pee on the carpet sometimes, but at least I don’t have to spend hours figuring out why!

Your thoughts on the subject are welcome. PLEASE! We women (and men, I suppose) need to stick together.


Author: Karen Y. Hamilton

Walt Whitman says about his autobiography, Specimen Days “…At any rate I obey my happy hour’s command, which seems curiously imperative. May-be, if don’t do anything else, I shall send out the most wayward, spontaneous, fragmentary book ever printed.” This is what I feel at this juncture of my life, the need to gather together memories of my ancestors as well as my own memories into some semblance of order. Because all of those fragments, all of the fragments that make up any life, become stories. I am the mother of three sons, who affectionately (I hope!) call me 'gypsy mom' because I tend to wander around a bit soaking in the universe's wonders. I am currently working towards an MFA in Creative Writing at Florida Atlantic University. I have published essays with Heritage Press, Florida Living, and the St. Pauls Review. I am currently working on a book of poems about the Florida Everglades pioneers and a memoir about grief and the bonds of friendship. I live in my hometown, Jupiter, Florida and work as a freelance writer and curriculum specialist.

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