The Harsh Realities of Being a Woman Online and Dating in Your 50's ...


The Harsh Realities of Being a Woman Online and Dating in Your 50's ...
The Harsh Realities of Being a Woman Online and Dating in Your 50's ...

Most of us have raised our children, had one or two marriages accomplished, know what we want and think it's our aha moment to go online and find a friend for dating and companionship or a relationship…………….wrong!

Speaking from lots of experience and the long conversations with my diverse group of girlfriends this is what we have found in the online dating world:

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The More Attractive You Are the Less Chances You Have…

Men are intimidated babies, turns out.


It seems counterintuitive, but catching an eye can sometimes mean catching less fish in the sea of online dating. When you've still got it, and your profile screams elegance and grace, the cyberspace Romeos often hit pause, wary of their own worthiness. It’s like walking into a high-stakes poker game with a royal flush; everyone assumes you're out of their league. So, you sit, waiting for a message that rarely ding, reflective of a strange paradox where beauty can be lonely, especially when seeking genuine connection beyond the pixels.


Forget It if You Are in Business

Same goes for accomplished businesswomen. Who knew?


For women who've built empires, climbed corporate ladders, and shattered glass ceilings, finding an equal match can feel like a job search without any promising candidates. Ageism and sexism often weave a dual thread of resistance, causing some to undervalue the achievements and depth of experience these powerhouses bring to the table. And while society salutes their boardroom victories, it often fumbles to recognize their hearts' desires—companionship, understanding, and emotional investment—deeming them too complex or intimidating to approach. It’s a poignant reminder that personal success doesn't shield one from the stings of stereotype.


If Your Not Slender or Athletic ...

Your hits are numbered, but you will get the 80 year olds.


Unfortunately, the digital dating scene can be downright brutal when it comes to appearance, especially for women who aren't in their 20s or 30s anymore. That's because society still peddles the myth that 'youth equals attractiveness'. If you’re not fitting into the narrow beauty standards - like being slender or having an athletic build - your inbox might suffer, while gentlemen of a certain age seem to think you're just their speed. And while there's nothing wrong with attracting or dating an older cohort, it's the limiting stereotype and ageism that can make the online search for love disheartening at best.


You Start Conversing with Someone and That’s Exactly What It Will Be…

A “pen pal” … NOT! For some reason these men just want someone to talk to never ask to meet but they are very good at asking for your number and then texting you…..endlessly…good morning 14 days in a row. After a bit of that I tell them to find a “pen pal”.


This merry-go-round of monotony is more tiresome than spinning my wheels at a singles mixer. It's all emoticons and empty promises of a future coffee that somehow always gets lost in a sea of "LOLs" and "How was your day?" texts. The hunt for genuine connection seems lost in a digital quagmire where the rules are unclear and the endgame perpetually murky. Enough to make a gal want to throw her smartphone out the window and resurrect the charm of a good ol' fashioned face-to-face rendezvous.


How about the Ones That do Want to See You

And then say “lets hang out” or “are you making dinner”…..are they kidding me?


Now You Finally Get a Proper Date ...

You have drinks or dinner and before you have swallowed your last bite of food they say “want to go somewhere else” when I respond “sure” they say “how bout your place”??? Now it’s a hook up?? Ugh!!! Kill me……….


Now You Finally Meet Someone Who Says He is Old Fashioned ...

Just as you asked for in your profile. You have 2 dinner dates and here it is....”are you ever inviting me back to your place”? Ever?? Its been two dates? I say I want to take my time and get to know someone and he says “so do I”.....he seems like a potential so I don’t want to blow it by giving him the “milk for free”.

We have 3 more dinner dates he talks about doing all kinds of things together, I really like him and agree. On the 7th date it happens…..guess what?

Yup…..never called again. The poison pen letter I sent to him is too crude to publish here….


I Saved the Best for Last: I Got That Gut Feeling That I Have Met the One!

Sounds funny at 56 to say that but I did. He is in my hometown of Boston which I visit for business several times a year. We literally talk on the phone every day for three months until I visit.

I meet him and instantly knew it…we have dinner, went elsewhere had a wonderful nite. He and I both verbalized our feelings. He asked me to stay with him for the weekend.

Against my better judgement and going strictly with my heart, I agree. When I tell you we cooked together (both being foodies), we took our dogs to the beach (I fly with mine), we walked, talked, watched movies, laughed our heads off and had the absolute best sex eva!!! (That says a lot for me because I am not inexperienced) ha ha.

As it approaches time to leave and go back to the place I am staying I sense a strangeness. I will tell you at this age my intuition is spot on. I ask him what's wrong, he says: nothing.

Go ahead ask me….did I hear from him again? Nope! I was literally devastated. I didn’t recover for months and I am one tough broad! I confronted him and he said: “you're just too fancy for me”… your clothing, lifestyle etc., you even dress your dog!!!!


Are You Kidding Me? after 3 Blissful Days He Decides That?

What transpired after that I could never repeat….what I can tell you is I told him maybe he should elevate himself and find a pair of jeans that doesn’t show his ass crack when he bends over. That was the nicest thing I said. I did pull a “partial” Glen Close in that movie with Michael Douglas and enjoyed every second…scared him straight…maybe he will think twice before he does this to another women.

Well its been interesting and educational, every month I say I am taking my profile down but I never do. I guess I am a hopeless romantic thinking someday I will open my computer and see someone that sparks my interest and he will be “the one”. I don’t even know if I really want “the one” again…

After 6 engagements and three marriages in my life wouldn't you think I would be happy with me and my dog and my wonderful girlfriends?

I have come to realize regardless of our ages and what we have been through we all want a man that really loves us and has our back, experience all the things that love does to us…thank goodness I have a very strong faith and am a firm believer in fate; that what is meant to be…. will be…. or won't be.

I am good with that!


Feedback Junction

Where Thoughts and Opinions Converge

its very very hard and not like when we were in our 30's....

I am ready to go hide. I agree with your post

Am Ali Mubiru a sports coach/player from uganda east africa am single man to day in my country people asking me to go back in the boxing ring for three professional boxing fights were by idon,t have sponsor .So am looking for a penpal friend who can sponsor me to filfull the request of uganda iwill be very grateful if iget a penpal thank you

Wow. U are so good. May u post more often.

Why do you make it sound like there is no hope for us over 50????? Backward thinking there. We just haven't met the It who is right for us yet...he is out there...waiting for us.

So true about the online dating. Men are intimidated by us. We have our shit together and we click with them in all areas But then they say they're not ready for a commitment but still call you.

I loved this post! Dating after 50 is scary when the newer slimmer models are preferred.

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