What I Learned Dating Older Men

I’d like to preface this by saying that I am a recently unemployed early-twenty-something living la vida loca in the big city. This means that not only do I not know how to adult, but I also don’t really know how to date. My idea of a hot date is a cheap Chinese dinner, a seedy bar, and a lot of “I think I really like you, but I also kind of want to throw up from the seven-dollar bottle of wine I drank before we got here”.

That being said, I’ve definitely tried. I’ve dated around the block. I’ve had my fair share of good times, bad times, and times I’ve had to fast-forward into one-night-stands because I’m pretty sure I never want to see them again. However, in all of my relationship exploits (and sexploits), none have quite matched up to the curiosity of dating an older man.

By older, I don’t mean “Billy’s finally got his license so he can go buy some vodkas for the girls” – I mean older. I mean aged. I mean well-versed in things like how to tell the difference between Hendrick’s and Gordon’s gin, and somehow proficient in budgeting and cleanliness. Things you and I young folk wouldn’t understand.

I mean old enough to be your dad. Or maybe even a little bit older than that.

As it turns out, if there’s one thing I do understand – chalk it up to an analytical mind – it’s the experience of dating an older man. I think my wealth of knowledge comes from the fact that I am a skinny gay boy, and that means older men are somehow drawn to me like flies to feces – or, as the slightly gross hint-hint-incest gay community expression often goes; like dads to sons. Yuck.

After reviewing some of these points with some straight female friends, we’ve agreed collectively that they all stand strong and true. In no way am I trying to suggest that younger guys are worse than older guys. These are just the experiences of one dangerously thin homosexual man, one oft mistaken for a sixteen-year-old girl.

So without further ado, here are some of the things I’ve learned dating older men.

They’re incredibly careful with you.

To them, you are practically a newborn. You are a proverbial clean slate, a starry-eyed youth preparing to take on the world, one cheap pot of beer at a time. If you text them while intoxicated after three or four pints, they will assume you’ve been smoking meth with criminals. They will plead with you to catch a cab to their house, where they will feed you water and bread, until you feel inclined to fellate them as a thank-you. Older men like to think you’re incapable of doing anything by yourself. Which is perfectly fine by me, so long as you keep booking those Ubers’ on your card and footing the bill at breakfast.

They’re constantly surprised that you might have a brain.

Maybe I don’t look like the sharpest tool in the shed, but I find it amazing just how many times I’ve had older men say to me, “Wow, you’re so mature for someone your age!” – Those words, in that exact order. It’s like they think that just because I’m in my early twenties, by default I spend my days doing nangs in a sharehouse, and giggling mindlessly over episodes of The Big Bang Theory while my mate packs a cone. Is Generation Y really doomed to have to prove themselves to old blokes time and time again? If you can hold a sentence together without so much as drooling down the side of your cheek, or looking like you’ve short-circuited, you’ve basically won their heart.

They want to recapture their youth vicariously through you.

Older men seem to have a crippling desire to return to their youth. Let’s face it – ageing happens, and when you hit a certain age, you start losing tautness and tone in places you were sure would never feel the effects of gravity. If it’s not the way they gaze lovingly upon me, as though I were the Taylor Swift to their succubi-Madonna – it’s the sheer number of beauty and anti-age products I’ve seen lining their bathroom cabinets and the tops of their shower stalls at any given time. When age starts to weary thee, the reality is, you want to know you’ve still ‘got it’ – and what better a way to achieve that than by doing a young person who is totally down? After all, you’re only as old as how you feel or who you’re feeling.

They’re collectively better in bed.

There, I said it. It’s the point you’ve all been waiting for. Young people might have more stamina and willingness to go at it than older people do, but older men just straight up know what they’re doing. And what’s better, they actually want to please you, and will not stop until you’re done. They want to know what you like, and they want to take it slow. They’re tactile, sensuous, appreciative and cautious at the best of times. Once you’ve been with a man who was probably married at some point in his long life, younger guys seem like selfish, mindless thrusting machines when it’s all said and done. Older men are just better in bed. And why wouldn’t they be? They’ve had years of practice.

Ultimately: I’m a kidult. A child masquerading as an adult. I am confused, askew and oftentimes dwindling in the wind, waiting for my next pot of Melbourne Bitter on tap to help me fail to understand the complexities of my existence. And sometimes, it’s nice to know that there’s someone out there who has at least figured half of it out. Who has trekked through life into a state of reasonable understanding, and has their own well-reasoned answers to my million tragic questions.

Maybe that’s the appeal of The Older Man – that they’ve perhaps got their shit together. Just as they might vicariously re-enjoy their youth through me; I might vicariously attempt to feel some sense of success through them.

If you’re curious about the ways and wiles of the mature older gentleman, or you’re up to feeling a tad objectified, or maybe you just want to know a bit more about how to save up super: Date an older man. Because even though they might not be exactly where it’s at – they’re where we’re all headed.
Words by Brandon Cook. Photo by Magnus.

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