
So a few weeks I wrote a blog post about my experience of jumping headfirst into the dating pool as 50 something only to realize it was the shallow end. That post generated views well above average. I don’t know if it’s because there are lot of 50 something singles out there or if it’s case of morbid interest, like a car accident. You don’t want to look, but somehow you can’t not look. Yes, folks, dating in one’s fifth decade is not for the faint-hearted. Nonetheless, it occurred to me that the tone of the post was perhaps too raw. It’s not all bad, there are a few upsides to dating more “experienced” women.
The following observations pertain to dating in an urban area of decent to significant size. (Where I live is different in significant ways, which I will touch on at the end of this post).
Benefit #1: If the person you meet for that first date happens to a) look like their picture and b) exhibits signs of sanity and c) isn’t bitter over a divorce, etc., then the dating dynamic is refreshingly free of bullshit. People in their 50s are much less likely to be inauthentic. They don’t have time for that, as they’ve probably tried that strategy in the past and know it ultimately doesn’t work. If the woman likes you, she’ll make it obvious because she knows from experience that men are fucking clueless and have the emotional intelligence of toddlers. And if she isn’t attracted, you’ll generally benefit from…
Benefit #2: Manners (aka less overt “rhymes with “witchiness””). In short, less attitude. Maybe this because (warning: politically incorrect observation incoming) they are no longer generating the same level of sexual interest from men that they had when they were younger. No doubt there is an element of that, but I also think that the older one gets the more one appreciates manners and consideration. In my experience, a normal woman my age will be gracious about handing you the “L” if she’s not interested. I’ve been on the receiving end of a few very well executed “no thank you”s that warranted a “golf clap” for skillful execution.
Benefit #3: Less likely to juggle multiple dudes at the same time. Women my age have been there, done that. They’ve drawn the conclusion that while there are some benefits (good for the ego, etc.) it’s ultimately not worth the hassle. They know from experience that the pigeons of one’s actions always come home to roost. I’m not saying it won’t happen to you, just that the risk of it happening is lower.
Benefit #4: Honesty. Women my age, like men my age, have come to the conclusion that honesty is best. Not because they are paragons of virtue, but because they’ve already given dishonesty an extended test drive. They know, from experience, that it’s a waste of time. In dating terms that means when I meet a normal, well adjusted woman my age, she’ll lay her cards on the table. She’s usually not going to hide something about herself or her situation that might potentially put her in a less favorable light. She knows that “it is what it is” and you’ll find out in due time anyway.
Benefit #5: Older women know what they want. If I had a dime for every woman I dated in my 20s who were perennially uncertain about almost everything, I’d have at least a few bucks. This is also why older women are honest. They’ve figured out that being up front about what they want is the quickest way of getting it. She’s not very sexual? She’ll tell you, to save you both time. Very sexual and/or has some kinky predilection? She owns it and doesn’t obsess over political correctness. Furthermore, letting you know at the start is an excellent filtering method. In both cases, your reasonable older guy will bow out gracefully if it’s not what he’s looking for.
So, you ask, what does the above mean in a real world situation? (As an aside, I only use Bumble because Tinder is nothing but fake accounts and besides, having the woman message you is simply more efficient. She will if she wants to, end of story.) It means that if a woman my age starts texting with you, she’s not messing around. She will want to do the normal amount of texting so we can both get feel if the other person is not unhinged or a fake. She’ll then expect you to ask her out, and will invariably accept said invitation. They generally are not fans of endless texting, which is great. Older women are much less likely to flake out. They show up for dates. At the end of the date, she will be honest if she is or is not up for a second date.
Here is the paradox that I’ve got no good explanation for: I have a pretty modest “hit rate” on the dating app in the city where I live. It must be said that calling it a “city” is being generous, it’s more of a large town. Additionally, the women my age here, on average, seem to have curiously high standards given all the variables in play. It’s harder to get a date, and it’s not uncommon for said woman to display at least some attitude (note: it can’t be blamed on culture, as this a very cosmopolitan city). Clearly, they feel they are in a seller’s market, and this is backed up by recent census data. This place has a very high density of international professionals and a . Conversely, whenever I am in a big city, it’s relatively easy to arrange a date with an objectively prettier woman who is usually easier going. It seems like it’s buyers’ market (from my perspective). I have never understood this, but it’s a real thing. Even as a young man, I noticed I’d have markedly better success in NYC and Montreal rather than smallish city where I lived. I wonder if some sociologist has already done a study of this phenomenon.








Leave a comment