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A Reason Why an Older Man Should Have an Age-Appropriate Partner

The resentment came bubbling out in our first phone contact

Brian Dickens Barrabee in Crow’s Feet: Life As We Age · 2026-07-12 15:13 · 230 claps · 2.1 min read paywalled
#dating #retirement #relationships #age #social-security
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Wiki topics: PFI · Personal Finance 🔒 · Cybersecurity 💑 · Relationships

A Reason Why an Older Man Should Have an Age-Appropriate Partner

The resentment came bubbling out in our first phone contact

Photo by Christina @ wocintechchat.com M on Unsplash

Photo by Christina @ wocintechchat.com M on Unsplash

I had been retired for a little over a year and divorced for close to three.

I’d had a couple of dates during that time of transition but nothing either the woman or I cared to pursue.

My divorce attorney and friend (Harold) advised me to try a dating app.

“Brian, you don’t have to meet the third Ms. Barrabee, you can just have fun!” Harold said. I know he was a grizzled veteran of the dating apps games people play. According to him, he had probably experienced most everything his pool of potential partners had thrown his way. He seemed to be able to pass off slights and rejection like someone who hailed a taxi cab on a rainy night only to have another rider jump in before him. Harold would just wait for the next available cab without batting an eye.

Truth

I thought long and hard before dipping my toe in the Match.com competition of partner seekers. I sought Harold’s counsel in having a professional picture taken and creating an attractive profile that was based on the truth presented in a positive way.

The important things — marital history, education, age, health and employment status — were all reported with stone cold accuracy.

Interests or lack of in music, religion, travel, enjoyment of plays and movies, I fudged a bit. However, the profile was essentially true.

My candidates

I was able to converse by either message, text or phone with any number of candidates. Harold’s prediction of online dating being fun was accurate. At least this part of it. I had yet to experience a legitimate in-person contact, however.

One evening I got a message from a physically attractive woman. She also happened to be quite a bit younger than I am.

Probably unwise to even follow it up. But, what the hell!

Over the phone she seemed to be all her profile purported her to be.

Can’t vouch for the accuracy of her picture though. We just talked, no Zoom or FaceTime.

She was, indeed, much younger than I. A good 20 years. She was working her way up the corporate ladder. We talked quite a bit about her career. She was pretty damned personable. She was someone in whom I saw… possibilities.

She told me she was recently divorced. She’d been married to a much older man who’d been retired.

“It used to piss me off!” she fumed.

“I’d be out there, working my ass off, contributing to the Social Security check he gets in the mail every month. Him — he just vegetated on the couch every day with his thumbs up his butt watching soaps and sports,” she lamented.

Hummm, I get a Social Security check every month.

He…could’ve been me!

I hung up the phone that night, still not having plans to meet any potential partner in person.

I’m having fun, though!

Right?


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2026-07-13 06:23:13