How To Date Well When You're Older, Or: Bad Habits You Young'uns Can Pick Up

“Of course you like getting older,” said the emails. “You’re a guy! When guys get older and fatter, they get more attractive. When women get older and fatter, they get ignored.”
That response came from writing a brief essay on Fet about how I felt stronger as I got older – more confident in my own skin, more capable, more responsible.  And a handful of women emailed me to tell me that the process is entirely different as you age if you’re not some skinny young thing, that loneliness is what happens to older women.
Yet I know several pudgy women in their late thirties who have to actively turn away new partners, because they are swamped with offers. I know several women in their late fifties who are still dating extensively, sometimes smooching it up with men decades younger.
There are lots of women who do get older, and quietly turn the color of woodwork, and fade from view like some wrinkled chameleon.
I think too many of ’em learned the wrong lesson.
Because what you often see with attractive people – men and women alike, though women are more often taught to rely on their looks – is that when they’re young and beautiful, they are beswarmed by suitors. They can’t order a goddamned drink without seventeen muscular young bohunks squirming in between them and the bar and offering vodka and oral sex.
So what gets taught to these attractive folks is passivity. People buy them tickets to concerts because folks like their arm candy skills. People text them, beg them, to come to the party. They email ’em on Fet: hey, you wanna get tied up? You wanna get candlewaxed? You wanna get photographed?
Some of them come to think that this is how you get a social life, not realizing all this special beauty comes with an expiration date.
And these people – who are not every attractive young person, mind you, but a subset thereof – don’t actually ever figure out what they want, because they’re continually being brought out to other people’s adventures. They’re getting offered so much that they don’t have to think about what satisfies ’em: it’s like forever eating at a huge buffet where you can have any kind of food, so you don’t pay attention to what those little pink things you love are called, they’re in there somewhere, you’re sure.
This is just eating. Eating comes with everything you like, always. Why bother investigating further?
Then those folks get a little older, and maybe a little saggier, and suddenly the options drop off. Part of that is because your social groups start to unwind when you hit your late twenties – things change when you’re not all going to the same college, and when some of your old friends are dropping out of your social circle as they have kids – but for these people, part of that is because they’re just not as physically luscious as they used to be. And after years of being offered things, going out and asking for things seems…
…well, pathetic.
So they sit, and feel ignored – because they are ignored. Maybe they go on some diets, get some plastic surgeries in an attempt to recoup some of that visual appeal.
Others, however, sit there and go, “Wait, I’m not getting the things I want? How the fuck do I get those?”
And they go off on bold adventures to a) figure out what they want, and b) go out and get that shit.
Here’s the thing about life: there’s all this talk about how “older men” are so attractive, but the truth is that most of those men aren’t. There are young women who are drawn to older guys, but they’re largely not drawn to stoop-shouldered accountants who stammer when placing an order at Burger King.
Who do they like? Men who have a good, solid handle on what they want, and aren’t afraid to ask for it.
Strip the genders off that concept. Then try this on for size: People like folks who have a good, solid handle on what they want, and aren’t afraid to ask for it.
“But Ferrett!” you cry. “Men don’t like pushy women the same way women like pushy men!”
For romantic purposes (not, say, career advice), I’d argue that approach is coming from that same logic of evolved scarcity: I used to have partners swarming me, now I have less of them, I don’t want to scare the remaining ones away by acting weird.
And you will scare people away by being forthright about your desires. It happens. I assure you, as someone who’s routinely shouting his opinions into a public space, I have tons of people who want nothing to do with me. Tons of people think I’m an asshole, they think I’m too melodramatic, they think I’m insensitive.
Hint: Though I find many of these people attractive, I am not dating them.
I both contract and expand my dating pool by being explicit about what I need.
Part of a good evolution into older age comes in understanding that you’re not going to be able to appeal to all the people you wanted. Maybe when you were young, you could wrap anyone you wanted around your little finger, so you had like an 80% hit rate between “attempted seduction” and “closing the deal.” That’s rare – but hey, if it happens, recognize that this hit rate is highly unlikely to continue into your sixties.
You need to understand that the best you can do is to find people who fucking love what you have to offer.
Like, for example, all these younger women who supposedly want older men. Does that list compromise all younger women? Hell no; not a day goes by I don’t stumble across some profile that says, “I won’t play with anyone over 30, it skeezes me out to play with someone who could be my Dad, don’t ask.” There’s plenty of women out there who will not date someone older, and God bless them. In fact, based on my OKCupid trawls, the number of young women who really need a 46-year-old balding dude in their life are in the minority.
Yet the reason those older men have done so well is that they speak confidently enough that the folks who do find That Kind Of Guy attractive can find them.
(And many – not all, but many – of them date at all ages. I do.)
Likewise, the older and beautifully bolder women I know don’t give a fuck when all those shallow idiots who only want some 22-year-old cutie ignore them: they’re too busy finding dudes who dig what they have to offer! They’re finding folks who are also into their fascination with theater, folks who are also into their love of costumery, folks who are also into their love of bicycle riding.
They’re not interested in dating, they’re interested in doing. And oh, how the dates follow when you start doing.
Yeah, there’s a hundred folks out there who don’t want you any more, just because you’re old. That’s sad. But the women I know, God bless them, have said, “Fuck it, I don’t care if they don’t like me, I’m gonna do the things I like and the partners will follow.”
And they date happily, thrillfully, zestfully. They lead a quirky life. Their boudoirs are stuffed full of whatever genitals they prefer to partake of.
And I’m not saying everyone can do this. Some folks don’t have the kind of personality to pull it off, and some people just aren’t that into things to make this happen, and other people are too shy. All of that happens. This isn’t a guarantee.
Yet I can say if you’re getting older, and you’re starting to feel yourself fading into the wallpaper – what do you have to lose? Give it a try. Be that old person who doesn’t give a fuck. Look at the older women who are still out there dating – they exist, go find ’em – and note what they’re doing.
Because man, there’s still a lot of fun to be had.