Hots for Teacher: An Introduction

by Charlie

We know very little about what motivates a young woman to date an older man. This became clear the day I Googled “dating older men.” My then-boyfriend and I were approaching our one-year anniversary. It hadn’t been the easiest year, but we managed, and I wanted to use every available resource to make things work. Including Google? Yes, so sue me. Anyway, of course, the results I got were totally useless. One article began something like: “Dating older men can be difficult. It’s not a pleasant situation when he asks for Bread and she goes to the kitchen instead of putting on his favorite LP.” In other words, if you’re a young woman dating an older man, you’re not expected to have intelligent thoughts about what your relationship means — just rummage through his LP collection and you’re golden. We can all assume youth is part of what makes her attractive to him, but why would a ripe young lady want to spend her time with an old fogey?

If you believe in soul mates and love at first sight and fairies and witchcraft, you’re probably thinking ‘age is but a number’ and ‘true love knows no boundaries.’ Bless you. I, on the other hand, believe everyone in relationships is looking for something, and the Katy Perry-loving schoolgirl in the kitchen slicing the baguette is no exception. And while young women aren’t actually supposed to know what they want, much less understand the complicated mind of a big, scaaaawy old man looking to score some fresh tail, this column will cut to the core (!) of what a young woman looks for when she dates a man who’s at least 10 years her senior.

Having enjoyed the company of several bags of dust over the years, I can attest to the fact that people can’t quite get their heads around the idea of a “little girl” who’s in control of or empowered by her relationship with an older man. Unless you’re a gold digger — a title to which women of all ages can aspire — you simply know not what you do and are enabling a dirty old lech. This assumption underestimates today’s younger women, and it’s time we set the record straight!

“Somewhere Nabokov is smiling, if you know what I mean,” Mary whispers to Yale in Manhattan, Woody Allen’s 1979 classic. Mary is an insufferable middle-aged pedant having an affair with Yale, a married professor. She’s just been introduced to 17-year-old Tracy, girlfriend of Yale’s best friend Isaac, who, at 42, is bursting with neuroses. He’s reached a point in his life where, suddenly, obsolescence comes into sharp focus and he questions what he has to show for his 42 years of life, how he’ll be remembered, all the things he hasn’t done. Etc., etc. He wants to return to a no-strings-attached life — no lesbian ex-wife, no shallow career, no best friend having an affair — and he wants to feel young. So he dates a woman 25 years his junior, duh.

This is a familiar story, to be sure — the young-woman-as-depression-fender-offer-slash-rusty-penis-dignifier trope is well established. We see Humbert Humberts and Lolitas everywhere in popular culture, but how often do we question their dynamic? The clichés are so ubiquitous — young woman as innocent, young woman as sacrificial victim, young woman as object of aging man’s sexual desire — that they don’t seem to deserve a critical examination. Manhattan ends with Tracy imparting some useful wisdom: “You have to have a little faith in people,” she tells Isaac.

O ye of little faith! Trust us: WE MAY BE YOUNG BUT WE KNOW WHAT WE’RE DOING. Dating older men is not always about a daddy complex or finding someone to bankroll a shopping addiction. As with every relationship there’s a lot of quid pro quo going on, just not always in the departments you’d expect. I like to think of it this way: dating older men is no different from dating any man — same deck of cards, different rules of engagement. We’ll go over some of these rules here, in subsequent columns.

Look, I’m not asking anyone to lower the age of consent, but I implore you! Cast aside your Freudian mumbo jumbo and hear us out! There’s certainly no shortage of advice on why dating older is a bad idea: “You want someone to grow old with, not someone you watch grow old,” “He’s never been married? Red flag!” “You don’t share the same life experiences,” “Do you want to have kids with someone who’s on the prune juice before the kids hit grade school?” Or the Lolita diagnosis: “You’re an independent girl looking for a father figure,” “You think he’s better in bed, but sex isn’t everything,” “You shouldn’t discriminate against your own age group.” And so on. But let’s talk about some of the reasons why dating older men is a GOOD idea.

Don’t get me wrong. Dating a man 10 years your senior (and then some) is not easy. Friends don’t take your relationship seriously. Run-of-the-mill questions are awkward to answer. And then there’s the parents. Ohhhhhhh, the parents. When you realize your boyfriend is closer to your father’s age than your own, you may vomit in your mouth a little. That’s normal. Dating someone much older than you is a constant struggle. TRUTH. But wouldn’t you rather deal with that struggle than force yourself to be with someone who doesn’t attract or inspire you? I was going to say, it’s just like those people who fall in love with their cousin or something, but then I realized, no, it’s not like that at all — it’s more like people who date outside of their race. And, here’s a humdinger for you: I’m also BLACK and generally date WHITE people.

Everyone has their “thing” in life, and I guess mine is dating old guys. But I’m not convinced it boils down to Electra and Agamemnon. There’s lots to think about, lots to reevaluate, modify, and update in a millennial context! What are today’s younger women looking for in an older man and WHY? So, without further ado, I give you “Hots For Teacher.” Do you have your pencil? I’m about to give you something to write on.

Charlie lives in Brooklyn. She also writes for The Awl. “Hots for Teacher” is a recurring column, and you’re welcome to email her with salacious news about your old man at