Barbells, books and…

This will be a short post. I will relate briefly what my experience has been in “dipping my toe” in the dating pool recently. If you are 50 something and are currently dating, I’m very, very curious to know what your experience has been. Please leave a comment below to let us know.

So, first things first. I’m a 50 something heterosexual male. I’m not bad looking. Most of my hair has gone white, but I still have hair. I’ve got a bit of gut. Otherwise, I look (as I’ve been told) younger than my age. Not to belabor a point, but as I have been strength training for years now I have more muscle than average, which can be considered a minus or a plus, depending on the woman in question. I have a pretty good career with decent level of responsibility. I have one adult child and one entering adulthood. I’m relatively well educated and have a wide range of interests. I’m housebroken and can carry on intelligent dinner party conversation. I’m not outgoing. I’m an introvert. I do love hanging with my friends, but I’m equally comfortable being alone. This is what I bring to the table.

I first re-entered the dating pool in my mid-40s when I first got separated and then divorced. For some reason, it was a much different experience then. I had a variety of experiences, yes, but overall I would categorize it as a fun, positive experience. It was relatively easy to meet women and most of the women I met had positive attitudes. I had some short term relationships as well as 3 longer term relationships since then. Approximately around the time of COVID, my last relationship ended. I was pretty burnt out on the relationship front, so the 18 month “no dating period” caused by Covid pretty much flew under the radar for me. I was very busy with work, with my children and also working on myself. I was not looking to date anyway, so it was moot point.

Roughly a year ago I thought, OK, time to start dating again. This time, though, I thought about what I wanted and what I didn’t want in a relationship. I decided that I wasn’t going to waste time on dating for dating’s sake. I wanted to find and attractive, self-confident, intelligent woman with her own interests and career. The idea is that we’d complement each other. I’m experienced enough to recognize red flags and why it’s imperative to avoid them. I’m looking for an relationship that is a net positive.

Methodology: I was looking for age appropriate women. Not because I am particularly woke, but I am realistic. Contrary to popular belief, there are no hordes of 30 something women just waiting to get with 50 something men, unless those men are well above average in income and/or fame. Also, I prefer a women with similar life experiences and I’m not looking to have any more children. So, I used dating sites as they are easiest way to meet women.

My experience turned out to be significantly different from my 40s. Firstly, there were less age-appropriate women to choose from. (I am about to make some honest, unfiltered observations. My intent is to honestly share my experience and impressions, not to denigrate or hurt anyone’s feelings.) Secondly, there were even less women who I found physically attractive. Some people don’t age well and for many people the 50s are when the pigeons of their bad life choices and/or DNA comes home to roost. I had to be honest with myself, I can’t entertain a relationship with a woman I’m not physically attracted to. Yes, I’m experienced enough to know that relationships are so much more than that, however it’s physical attraction that gets the relationship started. So that reduced the pool of date-able women even further.

Then there is the inherent weirdness and lopsidedness of internet dating. It’s a very shallow way of trying to meet somebody, but until matchmakers make a comeback, it’s the best method we have for now. You probably swipe left on some women who look better in person or whose personality would have made a difference. Yet, you learn quickly to spot profiles that are hiding something. Profiles with only picture of sunsets and inspirational quotes? Nyet. Fake profiles are so prevalent (but luckily easy to spot) that it makes the experience even more of a chore as you have to swipe through loads of fake ones to find a real one. Does her profile consist only of selfies taken from a looking straight up at the camera angle? Yep, there is a reason for that. Do the pictures look suspiciously dated (i.e. from the late 90s)? They probably are. Does she look sort of unhinged in her profile pictures? Then, dear reader, she probably is. Does the text in her profile give off major negative vibes? ”No ONS, no liars, no cheaters, etc., ” That just warns you that she’s made a lot of bad choices so far and is probably bitter. 

So, after way too much filtering through all of the above, I was able to find real women to go out with. I should preface by saying that I live in a small but cosmopolitan city. The choices are, as I’ve found on vacation, much better in a larger city. So what was my experience? I met some nice, attractive women and had some good dates. Some of those women I went on multiple dates with. And I briefly dated a woman exclusively for about 3 months. She was pretty, had a good career and sense of humor. Did I feel an ultimate “spark” with any of them? No, and if I’m being honest, I believe the feeling was mutual. Still those dates I definitely put in the “worth it” category.

Still, the majority of dates I went on were in the “not worth it” category. Some of them were mildly “not worth it” whilst some, unfortunately, were very much in the “holy shit, get me out of here” category. Let’s address the mild category first. These are the dates that when you arrive, you realize that the person really does not look much like their pictures (i.e., usually older and fatter) and/or you realize quickly there is no vibe, that your personalities are not a good match. This is the ‘no harm, no foul’ category, as they are nice, reasonable women, albeit not my cup of tea. Unfortunately, I realize that the older you get, there are two other prevalent categories, “Bitter AF” and “Complete Nutters”. You might ask, how was I unable to discern this from their profile or during the “texting” phase? All I can say is sometimes you can tell and other times they hide their game well, even past a first date sometimes. 

And I’ve stumbled upon a few women who were batshit crazy and that, my friends, is not a fun experience. As a man, you have to be very, very, very careful how you approach a woman. You must, in all of your actions, demonstrate that you are a calm, reasonable individual who poses no threat. There is a very good reason for this: most men can potentially pose a physical danger, so women must weed out the crazies. So dating rule number 1 is, or should be, take it slow and take it easy. Yet, on 2 separate occasions, I went on a date or two with a woman and decided to not pursue it any further. Before you ask; no, I did not sleep with these women and, yes, I did politely say it was nice to meet them. I clearly, but diplomatically, said I was not interested in further dates and wished them well. The result? Excessive (attempted) calls and texts (long rambling texts, filled with insults), stalking across social media and in real life, etc. I’ve had to block phone numbers, social media accounts and the like. One of the women became enraged that I wasn’t answering her every text immediately while I was at work. As in a series of 20 texts at a time. Her texts read like a monologue. It would start with a question – of course, even if I wanted to I wouldn’t have had time to respond, then would come a torrent of insults. Then veiled, and not so veiled, threats and finally an apology of sorts. Of course I blocked the number quickly but I archived the texts because, hey, you never know. Really, really creepy. As a male friend remarked, if I had acted like these women it’s safe to say that I’d have been contacted by the police for questioning.

Yes, of course this happens to women, too. The experience has made me realize how scary it must be for them. Unlike a woman, at no point in time did I feel like I was in physical danger, but was it was unsettling. Crazy people, you come to realize, have no rule book. So internet dating does not come without risks, folks. Don’t give out your phone number or discuss any personal details until you fairly certain you are dealing with a sane individual.

My overall conclusion from this experience is that it doesn’t now seem like the juice is worth the squeeze. I will continue to concentrate on my family, my career and interests. If a compatible, trustworthy woman somehow materializes in the future, I’m more than open to it. However, I’ve given up on internet dating – at least where I live. Sifting through all the fake profiles, the bitter ones and the crazy ones to have an occasional nice date isn’t worth my time or energy. Like I said before, I’m very comfortable being on my own. 

If you are 50 something and now dating, what is your experience? I’m especially interested in women’s experiences. Was it similar? How was it different?

In spite of the minefield that is internet dating, there are some advantages to dating a 50-something woman. Click here to find out.