Would you seek dating advice from the worst guy possible?
Yes, that would be me.
However, in the past two weeks, three people — yes three —sought out advice from me, a man who met my wife before the Internet existed. When people socialized in person and all that.
BTW, I’m a Gen Xer.
But that does not mean that I have had my head buried in the sand for the past several decades. Despite my crushing depression and suicidality, I still try to be the nice guy that I have always been and also improve my empathy and support for others, especially those few people who I actually like.
So if one person sought out my advice, it’s obviously no big deal. Nothing worth noting, let alone write about.
When two people ask, you begin wondering if they think you know something or have some pearl of wisdom to share with them.
When three ask, a wannabe writer like me feels that it’s time to puke up some words and publish.
My work wife
I have been meaning, and eventually will, write about my work wife.
For those of you unfamiliar with the term, according to artificial intelligence, something that I sometimes utilize but mostly fear and loathe,
In informal workplace settings, the term “work wife” or “work husband” is often used to describe a close, platonic relationship between two colleagues, typically of different genders, who share a strong bond and support each other in a manner similar to that of a romantic partner.
This relationship may involve things like confiding in each other, offering emotional support, and collaborating closely on work-related tasks. It’s a term used to describe a special, non-romantic connection between coworkers. However, it’s essential to recognize that the use of such terms can vary by workplace culture and individual preferences, and not everyone may be comfortable with these labels or their implications.
As you may have surmised, my department’s administrative assistant is my work wife. We have grown quite close over the six-plus years that I have been in the department.
She is divorced with two grown men children, one who is independent and getting married soon, the other who resides on her dime at her home.
She dipped into the online dating app world and asked me to weigh in. Mostly, she complained about it, like most women do. Those apps do seem like a meat market set up for men shopping for sex.
Let’s be honest — isn’t that what they are?
She asked me what I thought of a few guys who looked like brawny sixty-ish-year-old guys with divorces and other messy things in their backgrounds.
They all looked kind of like jerks to me.
I truly like my work wife, but besides having a great body and being health conscious, she is not the most attractive woman around. She is also extremely finicky and nervous, in general. I do not think that I would date her if I were a single man a few years older than I am.
I told her that one of the guys looked okayish and, after all, they were just going to meet for dinner in town, so it’s not like she had to commit to anything beyond that.
She knows what a manly man I am, so I was fine with telling her that this particular right-swipe is a fairly good-looking guy. She chuckled and agreed and, more importantly, accepted a date with him.
I write these words on the Saturday following her Friday evening date, thus will hear some deets if I ask next week.
I am glad that I am not on one of those apps, at least not at this time.
My photo would not attract lots of babes.
Speaking of babes…
On Tuesdays and Thursdays, I stop by a dojo in the downtown of the city where I work at the beginning of my lunch hour and “pick up” one of the most beautiful women you could imagine. My walks with her now comprise two of the best hours of my week and ones that I very much look forward to.
She is a widow, her late husband having passed away from lung failure late last year. Many years prior to that, she was divorced and, even before that, she bore a child by her high school boyfriend. Not only was he the star QB of the high school they attended, but he went on to become the starting QB for Iowa State after that.
My walking friend is about to attend a high school reunion.
Guess who is going to be there?
You guessed it!
Not only is he going to be there, but he is now fabulously wealthy and owns an estate with many acres in the south. She is going to pick him up at O’Hare and he is going to stay with her which makes me jealous although I obviously do not have any right to be.
She asked if I thought it appropriate for her to date or become involved with someone less than a year after the passing of her late husband and if she thought that men would think less of her because of it.
She additionally asked me what she should do if he tries to kiss her and added that he might want to fuck her.
I was left speechless, to which she reminded me that we are adults here.
True, but it was still unsettling for me to hear that word come from the mouth of this beautiful woman who I have a low-key crush on. I felt myself blushing.
She took some delight in my discomfort. Even though we are platonic friends, I have never before conversed in such a way with a beautiful middle-aged woman. I do not think that I have ever heard my wife utter that word in thirty years!
What I did was blundered so badly and gave a ten-minute-long speech that I would give my daughter. Something about seeing if they still click and how they feel about each other.
I felt so bad about my stupid answer that I once again turned to Chat GPT, that knower of some, to provide a more suitable answer.
The next time that I saw her, I apologized to her for my blundering long-winded advice and told her what I had meant to say (with the aid of artificial intelligence). Basically, that it is well within her right to pursue happiness, and if a man takes issue with her recent widowhood, that’s on him, not her.
Personally, it would not bother me. Multiple divorces would, but death would not.
Another story for another time, I made an almost pass at her the last time that we saw each other. Dear Reader, keep in mind that I have never cheated on my better half, but that does not mean that I am completely immune to temptation.
I shall never attempt one again with her but will definitely inquire about how it went with her first love after the passage of so many years.
A male friend
I have repeatedly shared that nearly everyone we associate with is wealthier than we are. Many of them by far. Our family’s friends and relatives, and most of those who I work with, are the types whose wealth increased since the pandemic began. They are rent collectors, not payers. They are professionals, business owners, and some are heirs to vast fortunes.
I share this because so many Medium stories are about those who are fake and pretend to possess wealth. Our friends and relatives are the opposite. Despite their lavish homes, vehicles, and lifestyles, most of them act and dress completely normal and you would not know they are wealthy if you met them.
For the most part, they practice the art of stealth wealth.
The man in question fits that profile. Making at least half a million per year, he dresses mostly in athletic clothes, works from home most of the time, hangs out in local establishments with other locals, and just purchased a used Prius with over 100,000 miles on it.
You would not know that he is a multimillionaire unless you observed him over the course of a few days or spent time with him, as I have.
He also happens to be very handsome and a bodybuilder. And separated from his wife and in the dating pool.
TBH, he does date and fuck a hell of a lot of women that he meets on Tinder. Just as my work wife lamented, this man is one who shops for hot women the way I purchase alcoholic beverages. On a regular basis.
When I looked at some of the women who mutually swiped right with him, my eyes nearly popped out of my head. These are some seriously hot women, hotter and, of course, far younger than the beautiful woman who I walk with. Even though this man is entering his late forties, not one of the women he dates was born when my lady friend graduated in the mid-eighties.
Many are closer to my son’s age, which is twenty-five.
I have not looked at this man’s profile, but if he shared a nice photo along with the basic facts, he would seriously be one of the most eligible men in his area.
His problem is somewhat the opposite of the women’s, and it is further complicated by him eventually having to explain that technically he remains married. Basically for insurance purposes.
He admittedly enjoys having sex with different hot women on a regular basis.
Who wouldn’t?
But he lamented to me that he is having trouble in his area finding educated mature single women who have not been divorced multiple times already or have other myriad issues. Sometimes when they find out more about who he is, they might also only see dollar signs rather than the long, arduous road that he took to get where he is. He also has three children, whom he has joint custody of.
In other words, there are not too many eligible women of his wife’s stature around who see him as much more than a ticket to an easy and rich life.
He considers me, of all people, as someone to seek advice from and asked for some.
I admitted to never even having looked at a dating app, him asking prior to when my administrative person (I didn’t say “work wife”) asked me to look at a few profiles with her.
He knows that I never sought out companionship online, having met my wife of twenty-seven years way the hell back in 1990. I had plenty of girlfriends around that time including two — or possibly three depending on how you define it — at once.
But I met them all in person. One through my summer job at the park district, one in my sophomore year Spanish class, and another after I moved out of a crappy dorm and into an apartment across the hall from her. That’s the one who I still spend time with every day and night.
But being the helpful guy that I try to be, I told this friend the truth, as old-fashioned as it is.
I simply don’t know!
If I had to find someone worthy of dating, obviously my first choice would be the woman who I walk with. But if I had not met her when I did, I would join some local clubs, attend seminars, take non-credit classes, and the like.
I am in serious need of meditation and found a class on Monday nights in the area. I’d bet some nice women go to that!
Someone will ultimately take offense, which I am just fine with, but I would not spend too much time in bars trying to find a suitable match. It may work for some, but would not for me. A suitable match for a night, or perhaps a few weeks, months, or even years. But not a permanent suitable match.
I also know that some people do succeed in finding the love of their lives on dating apps. I have heard such stories.
But more often than not, those apps are better suited for serial dating and hook-ups.
There are even some extremely good matches right here on Medium, but there is no official Medium dating service and the few women that I have hit it off with here live hundreds, if not thousands, of miles from the northwest burbs of Chicago.
Plus I’m married.
But if I wasn’t…
I know that I would be highly eligible in a number of venues including local synagogues. The very few times that I attend, the mostly older crowd gets excited and I get low-key “recruited.”
I only go for the high holidays and did not attend this year, mostly due to my deep depression.
But when I do, they see a promise for the future, and the middle-aged divorced or, in some cases, never-married women see a fair-skinned, lighter-haired, relatively fit “5” to “6” who at least used to exude some confidence. These days, not so much.
Perhaps I would sit in cafes and read, hoping to make eye contact and strike up a conversation with a woman should the opportunity ever arise. I am not too fond of women who don’t read. But many women also consider it creepy if you try to strike up an actual conversation with them. If you are super handsome, it’s not creepy, but if they do not find you attractive, then it is.
I do not know where else a middle-aged man like me would seek out companionship. Perhaps provide an opportunity for a young war widow, but that would probably work out less well than meeting a woman in a bar.
The truth is that I don’t know.
And if you need dating advice, you should ask almost anybody else besides me.
Just click on the next story in this publication.
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This post was previously published on medium.com.
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From The Good Men Project on Medium
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