Life as a Wandering Widower: Finding Purpose at 69


Hello America, It’s Feb. 5th, 2025, a whole 15 degrees outside this am here in Westborough, Ma. Seems, where I live here in Westborough, Ma., in a 55 plus community, there are very few men like me, I am a widower and it seems lots of single women here, but few of us single men. While that is nice at times, I am also very rare in the fact I don’t chase women. Now, don’t get me wrong folks, I love women in many ways, for many reasons, I just know better than to chase them, in such a community.

When you get older folks, like I am at 69, you know that in such a 55 plus community, if you get involved with anyone of the opposite sex or gender here, it can turn into one hell of a mess. I bought the condo I live in after my wife passed, thinking it is all I need for me, at 956 square feet, no more snow shoveling or yard work either. Then, I move din and have come to realize, while there are many and I many many widows or divorced or even solo women, living here too. They outnumber me by big numbers and I figured there has to be more single men around right? Well, we are indeed as I have been told a rare breed, here in this complex. So, what to do is the question. I told myself not to try to date any women here, on the grounds of big problems occurring if, the relationship doesn’t work out. Women talk, and as we all know in anger, women can be cruel or indifferent and they gossip and it spreads like fire in such a community. So I stay alone, I don’t approach, I don’t chase and I don’t ask out any of the ladies here. Which leads me to a lonely existence here in my community.

So, I tried online dating sites, like Match, Zoosk, Our Time and such and found that they take your money but, there is no guarantee you even get a date on them. If you do, it seems the women on them are still working trying to survive and have no real time for dating. It is hard to get a match through online dating sites, many fake profiles and fake pictures. Also, liars who, say they want one thing and do another and only want a man for his wallet. Momma didn’t raise any fool, so my wallet stays in my pocket unless I wish to use it, not to give away, what I have earned.

At 69, I am five foot 8, 190 lbs, brown eyes and short hair almost bald, with a goatee. I am not what I call a handsome man like Rock Hudson was, but I am not Mr. Ugly either. I like to laugh, I write poetry and short stories and blogs, like this one. I like to play billiards and bowl also. I like to walk when weather and temperatures allow, or I will walk the mall around the corner from me. In warmer weather, I like walking more, I like fishing, in good weather. I read a good amount of time, I like books, on History, politics, mysteries or biographies of famous people. Used to be I could find a way to spend a couple of hours in a Barnes and Noble Bookstore, these days ya can’t even find one near me. So, Every now and then I stop in the small book store in town and look around.

I am not a drinker really, I may have a beer or two for social reasons, like if I meet someone socially, or such. I never did like drinking and have a problem with those who over do at it. I don’t do drugs, unless it is for medical purposes, and yes, I can be 4/20 friendly. I do gummies only for pain in my back, and i have my Medical Cannabis card for that now. But, overall, I stay to myself, and try to just live day to day, it is in fact, a boring lifestyle for me. I get bored fast with being alone, but, I have been this way since my wife passed in 2021. I thought of looking for someone to date, but, finding someone who is compatible, fun, has a sense of adventure in them and a sense of humor is not easy in today’s world at my age of 69. Life it seems, is not so easy, retired and a widower, but I do my thing, and I get by, although, I date no woman, at this time and the few I have met, were nice enough, but, there seems to be a lack of chemistry, at least for me.

If there are any single or widowed women around who have an interest in me, I have not heard a peep out of them. Even in my own condo community here. I guess I am not there type, or not funny enough, or not good looking enough or whatever, so I wander alone. I am not big on events or going to bars, I like small groups not large. I would not last long in a bar situation, alone. I get bored and I sit alone in those situations and one would probably see me at the bar, eating a sandwich and fries and one beer, and leaving, I don’t stay long. Why, I don’t feel comfortable as a single, bouncing around a club, bar or tavern alone. Never have, and in todays world, if you say one thing wrong to anyone here in Mass. it’s fight on, and I don’t like to argue or fight, especially in public at all.

Anyway, that’s my thoughts for Feb. 5th, 2025, the Super Bowl is next come the 9th, I love the NFL and watching games, I like the NBA and Celtics too, and I am a Red Sox Fan, but not a very avid follower, because the game is too long and puts me to sleep, frankly. So, at 69, I am what is known as a wandering widower, who does so aimlessly, and without real purpose and who is basically, the same guy, I have always been, a bit of an introvert. That’s me, the guy most women overlook and the one who may spot you from across the room ladies, but, never make a move. I never did learn to flirt, my first wife, I met in The Navy when serving, my second wife I asked to dance at a Singles Dance. The first marriage lasted 12 years, the second 28. Add them together I had a total of 40 years of marriage in my 69 years, not bad ya ask me. But, as most will know in today’s world, there is a loneliness syndrome that is currently happening, plenty of people, but lots of fears out there, so alone I guess is my destiny. Ok later folks, have a good day, enjoy.

3 thoughts on “Life as a Wandering Widower: Finding Purpose at 69

  1. Would like to respond to you but am not sure if there is a connecting link somewhere. I, too, am a widow and moved to a small over 55 condo community in Marlborough, just over the Southborough line. I moved here in July. Everyone is very nice. I dont think there are any single/widowed men but am not sure. One of my neighbors took me to Lake Chauncey recently and I thought it was a beautiful area. My plan is to bring my dog for a walk over that way. Weather permitting, if you’d like to walk and talk with me, I’d welcome the company. No expectations, just a nice walk and conversation. KarenMehegan624@gmail.com.

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  2. Try plenty of fish. https://www.pof.com/ https://www.reddit.com/r/datingoverforty/comments/10l9z04/plenty_of_fish/

    ANewBeginningNow • 2y ago
    POF is one of only a few I have used. A recent change made has cleaned up a lot of the bots, but it also allows only one free first contact per day as opposed to the two that was there briefly, and before that, I believe 55. This is for free members, paid members get more.

    There are genuine women on it, but also a lot that don’t bother to fill out their profiles or make any effort whatsoever. Because I’m real good at filtering out those worth it from those that aren’t, my experiences haven’t been horrible. But my issues have been the same as I imagine would be the case on more popular sites like Hinge or Bumble (which I haven’t tried), namely that my first contacts or likes aren’t returned or reciprocated and no first contacts from women at all.

    Like Bumble, there are a mix of women on POF that want serious relationships or are open to hook ups. I would say more want something serious than something casual. I don’t know about the men.

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    Gator-bro • 2y ago
    I had no problems with plenty of fish, the people on there seem to be older, but that was really the only thing different that I noticed about it. I’m actually dating somebody that I met on that site where we are. We are on month four

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