The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He's been on more dates than you can shake a lengthy bar tab at, and he's here to help the average guy step his dating game up a notch – or several. Need his help? Email email@example.com.
Hi Dating Nerd,
I'm a divorced guy in his early 50s. It's been a few months since the dust around my marriage settled, and I want to date again. Specifically, I want to hang out with younger women. I'm not a bad-looking guy and I've got a little disposable income. Can a guy like me date women in their twenties? How do I do it?
– Silver Fox
Hi Silver Fox,
Of course you can. That pretty girl who you see at the dog park every day? Your favorite waitress, on whom all your fantasies are recently pinned? Chances are, you can get in there. You might not think so, but it's entirely possible. Go for it.
This is made possibly by a weird asymmetry in heterosexual dating. It's frequently (although not universally) true that women are attracted to status and experience as much as looks, whereas men don't tend to be so well-rounded. As a result, if you're an older guy, you can make up for not being a bouncy, chiseled, 20-something yoga teacher named Jaysonn. With your superior wardrobe, and your real career, and the fact that you actually have some things to say, you can be attractive to women your junior.
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If you want to get younger girls and you can't, you're probably just not doing it right. And simple basic dating advice for single people applies in this situation: just be confident, wear a nice outfit, and be a slightly better version of your normal self. That sounds difficult, but it's really not. All confidence is fake confidence — confident people don't lack nervousness, they just look beyond it long enough to get a phone number. Male fashion isn't that hard — and if you can't figure out how to wear a white oxford and pants, just walk into a Brooks Brothers and point at a mannequin. And, finally, your personality is just fine — you don't need to learn any pickup artist hypnotism, just talk to your date like you would your best friend, except maybe with a few fewer dick jokes and a little more active listening.
And that's basically it. But I have a question in response to your question. Which is, why do you want to date younger women, specifically? Why is that what you want right now, as soon as you're out of a divorce? What's wrong with women your own age, or women just a few years younger than you?
I don't mean to shame you. Of course, younger women are great. There's the energy, the enthusiasm, and so on. Vulnerability and impressionability are often more attractive than cynicism. A lot of guys get criticized for dating younger people, and I don't mean to criticize you outright. Or at all. You do you. There's no shame in any consensual relationship between legal adults. I just want you to engage in a little self-examination here to make sure you're going to get what you want out of this.
Young people aren't stupid, exactly. It's not like they have fewer IQ points. But people in their early twenties of both sexes are, of course, immature — unformed. Either too sure of themselves or totally neurotic and insecure, or swinging rapidly between those extremes. Full of misguided enthusiasm and misplaced anger. And, frequently, unsure about what they want.
You can have a great relationship of a certain sort with this kind of person. If you meet a young woman on an online dating site and hit it off, she's probably going to get a lot of cool stuff out of it. You're probably way better in bed than her peers, just because, well, you've grabbed a boob before and you know how it's done. You can take her out to a nice restaurant and you know what wine to order, and what to do with the salad fork. All of that fun adult stuff. In return, you get the kind of bright, shiny energy that humans your age just don't have anymore. You get the starry-eyed wonder and the giddiness.
That's all great. But what you're not going to get, most probably, is a relationship with the kind of depth you'll get with someone your own age. Someone who's twenty just won't have any idea what it's like to deal with the stresses of a real job, or the ravages of aging, or the complexities of family. They won't have done battle with big human realities and discarded some of their dreams like you have. You'll be able to meaningfully share maybe 40% of what's really on your mind. It'll be a pretty simple relationship.
And, again. There's nothing wrong with that. If you want a little harmless fun, have the harmless fun. But if you're hurting right now, because, y'know, divorce is pretty bad, sleeping with young hot chicks might not be what you need. It might just make you feel more lonely. You might need someone who can meaningfully support you.
We live in a society that worships youth, and so we're told, as men, that a relationship with a sweet young woman is basically the best thing that can ever happen to your life and/or dick. And, while they can be pretty good, unfortunately, young women are just people. Nobody is the perfect sex goddess who's going to change your life. You can't drink from the fountain of youth and restore yourself forever by taking that barista on a weekend trip to Cartagena.
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Take my relationship with Anna. She was amazing. I have zero bad things to say about Anna. She was intelligent, affectionate, attentive, and took everything I said seriously. A little too seriously, in fact. Whenever we had a conversation about the future, or politics, or psychology, she would immediately, unthinkingly conform to my opinion. And it's not like I'm some sort of maximally persuasive genius. She wanted to make me happy, and she just hadn't had much time to fill in her own thought bubbles as an adult. So we didn't have debates, or discussions — we just had mutual admiration sessions. And, as much as I liked hearing myself talk, and seeing her nod, it was weird. I missed having a girlfriend my own age, who would call me on my B.S. if appropriate. I missed real dialogue and real connection.
Anna was really surprised when I broke up with her, after I got bored of our little fling. After all, I was an older schlub who should've considered myself very lucky to have the luxury of her company. And I was very lucky. It just wasn't the kind of luck I needed. Maybe you're totally dissimilar, and all you require is a quick rollick with someone half your age. But, on the other hand, you might be disappointed by your fantasy once it's reality.