Ask Polly: These Tortured Intellectual Boys Are Torturing Me!



I’m a 26 year-old woman living in a big city.

I’ve been in 3 serious relationships. The last one — the big one, the one that broke my heart and my soul and almost made me give up on love and all that junk — ended over a year ago. I’d been in love with him for about 2 years before we started dating. Once we did, it was a whirlwind of love and romantic weekends (we were long distance for most of the time). I felt that he was the one. I KNEW he was the one. He was smart and funny and honest with this biting pessimistic (and yet painfully accurate) sarcasm. He wasn’t always so good at being part of the world. And while, on the one hand, I liked that he was different, you know, a ‘rule breaker,’ ‘not just your average everyday accountant,’ a ‘critical thinker,’ etc., it was also pretty annoying that he had a hard time making dinner plans more than an hour in advance or that he didn’t have too many qualms about leaving a social situation on his own terms. He would just suddenly ‘not feel like’ something anymore, and that was that. He also very possibly suffered (or still suffers) from depression.

I know, you might be like ‘hmmm, this guy doesn’t sound so awesome.’ You’re Polly — you’re perceptive like that. But to me, at the time, I just didn’t care about his Asperger-like social tendencies. I was head over heels. My eyes had turned to stars! Our GChat conversations were the highlight of my work days. We debated. We theorized. We analyzed. I worked to convince him that the world wasn’t SUCH a horrible place. A more astute person (or therapist) might also say that I enjoyed the idea of myself as the optimistic fairy princess who saved him.

Except, as it turns out, he didn’t want to be saved. After the honeymoon period of our first months together faded away, he just wanted to be alone. I learned this the hard way, when he broke up with me a month after I moved to his city.

It took a while, but I’m over it. Had my mourning period. Had my ‘focusing on myself’ months. Now I’m ready to move on! Strapping on those dating boots!

So why am I writing you?

Because, okay. Here I am. Dating again. Except most of the guys I meet (in person, and on OK Cupid) are so so MEH to me. So boring. Sure, we might have a mildly interesting conversation, maybe. But most guys don’t like to debate about theoretical things. Or they’re amused by me, but then they’d rather talk about movies. In essence — I’m bored by them. I don’t give a flip if they text or don’t text ever again. I don’t give a flip if they try to kiss me or not. Maybe I’ll kiss them back, but I won’t give a flip about the kissing either. I’ll just be bored.

Obviously I haven’t tried every single guy out there, but it’s starting to worry me that the only guys I really find myself attracted to are the tortured intellectual types. Like my ex. Or, in their own ways, like my other exes before him. Every guy I’ve seriously liked has been incredibly head-smart and heart-dumb, and, more often than not, has some mild psychological issues to boot (more like depression that sociopathy, but still).

I know I should just fall in love with someone more… normal (I know, no one is actually “normal,” but hopefully you know what I mean). These guys aren’t good for me! They’re usually too self-involved to seriously commit to a long-term relationship. And my friends never like them (the world “asshole” has been used a time or two). I realize that I shouldn’t date someone that I’m trying to “save” or “change.” Trust me, I will never again try to change a guy! But is there something wrong with the way I’m seeing men here? Or maybe all the smart-but-not-damaged ones are taken?

Why is dating so hard, Polly? And why am I into the wrong ones?


Turned on by Intellectual Assholes


Hello, mineral-rich soil of a letter, begging to be plowed and planted and watered and mountain-top-mined for every ounce of wealth you offer. But where do I start, TOBIA? So many paths to follow here! Sometimes there’s so much beauty in the world, I feel like I can’t take it, and my heart is just going to cave in.

That last part is a quote by Ricky Fitts, the weird kid next door in American Beauty. He’s talking about the footage he shot of a plastic bag, floating around in the air. I mean, ungh, who doesn’t love that haunted little theorist boy. He’s a greasy morsel of perfection. He’s the moody dream boy of every smart girl’s high-def fantasy. Beautiful eyes, tortured family life, a tiny bit creepy, pretty depressed. Wes Bentley, yes indeedy.

But let’s flash ahead to fifteen years later in our story, shall we? Having fallen madly in love, Jane (played by Thora Birch!) and Ricky now share a little apartment in the big city, and Jane is working nights as a registered nurse because Ricky went to NYU film school and then spent a year making a short film. Then he spent a few years working as a grip, but he finally decided that the industry was total fucking bullshit. So now he’s getting a PhD in philosophy, theoretically. Except mostly he just smokes pot and speaks in abstractions. And theorizes. And analyzes. And Jane is 33 and would like to have a kid in spite of the traumas of her past. But Ricky says he needs to be in a very, very different place in his life before he even CONSIDERS such a wild and crazy far-away fantasy world.

In other words, Ricky is as pragmatic and future-focused as a squid out of water, lolling about on a linoleum floor. He’s a human throw pillow. He’s a plastic bag that floats around in advance of a snowstorm for fifteen minutes straight, and then just sits on the ground getting soggy the rest of the time. He does look really beautiful, floating around. But still.

For Ricky, floating started out as a way of finding himself. It was still sexy then! But now floating is just a giant excuse for not really living yet. It’s an excuse to leave a party — OR a relationship — the very first second you feel vaguely dissatisfied.

Hey, to each his own. Seriously. Go forth and do you, sweet cheeks.

We’re not talking to Ricky, though. We’re talking to you, Jane/TOBIA. Could your ex foresee dumping you before you relocated your entire life to be with him? Fuck no, he could not. He required those sinking feelings that came along with you making practical plans in his midst, and then he needed one full month of the two of you, not just fucking and being dreamily perfect together. There you were, messing up all of his floating by requiring him to show up places and do things. Motherfucking doing things! So overrated!

Just imagine all of the other shit that might’ve turned out to be completely beyond his control, over the course of a few more years. You dodged a bullet.

But don’t tell me “You’re Polly, you’re perceptive.” I was pretty perceptive twenty years ago, but I still did all kinds of crazy stupid stuff. I look back on my boyfriends over the years, and Jesus, they were different from each other. Even so, most of them were squid boys, throw pillow guys, flying plastic bag men. But not on the surface! On the surface, they seemed pretty productive and normal. But underneath, they couldn’t deal. How did that happen? Why did I end up with that kind of flailing, future-avoidant, convention-eschewing guy?

Here’s why — PAY ATTENTION! Because when you meet a plastic-bag man, you can immediately see how you’ll fit into his life. And that’s exciting. It doesn’t mean he seems needy, or that he even likes you all that much. But somehow, you can see the holes that need filling. You can fill them. You’re good at filling holes! Really good!

Example: The recently dumped oldish guy with the really depressed dog. This dog needs a walk! This oldish guy needs a (younger) lady who’s sweet and kind, who’ll never leave him! The pull of that vision on you, in his life, fixing everything, is strong indeed, overpowering all of the other stuff that should be repelling you, like the fact that his ex seems perfectly ok and she hates his fucking guts.

This vision is so strong that, when you go for a walk with the dog for the first time, and he shows you how to pick up the dog’s shit? You are appalled, but you don’t immediately smile politely, say goodbye, get in your car, and get the fuck out of there. (Yeah! Go get some doughnuts! Rent a movie! Celebrate!) You stay. But did you indicate the slightest interest in his dog’s shits? That should have been a blaring red alarm. Did you heed it? No, you told yourself, “Look how serious he is. He sees a future for us, together, picking up lots of shit.”

Heh, there’s the other thing. When a guy is serious and intense, that can feel so refreshing. After a series of encounters with casual whatever fuckwadery, that intensity can be tough to resist. He looks you in the eyes? Incredible! And he says heavy shit, and analyzes and theorizes? And not just about Federer’s tactical failings?

Seriousness and a hunger for analysis, that’s lady catnip. But it’s also, sometimes, a sign that your guy knows his target demographic pretty goddamn well. Or that he’s depressed. Or that he’s a tedious self-centered overly analytical slithering self-adoring sea monster.

Now, let’s move from the intriguing, serious, heavy ones to boring, light, dull ones. You put on your dating boots, then fall asleep in them. Here’s something to keep in mind: Some guys who talk about dull stuff, politely, without a lot of frisson or passion? They’re just trying to act normal on a fucking date. They’re trying not to trot out the full-bore crazy immediately. They know from experience that not every woman alive loves analysis, and theorizing, and debate. See? THEY’RE SANE ENOUGH TO HIDE SOME OF THEIR CRAZY. And the older you are, the more you understand that that’s about as sane as it gets, folks. Sane enough to seem sane? That’s pretty goddamn sane, actually.

Now no one is endorsing the guy who talks about sports and televised entertainments, endlessly, on your first date. No one is saying that’s your guy.

But a guy who talks about his job, and it’s kind of dull, and he talks about his favorite cable drama, and that’s a little boring, and he talks about moutain biking or surfing or some romanticized take on moving around outdoors, and that’s sort of a snooze? And he touches on a past relationship, demonstrates that he has a brain and some emotions, but doesn’t go into it, and doesn’t make it into an interesting story? Maybe he’s casual, easy come easy go, and seems not all that attached to seeing you again? Or worse, he seems interested, but maybe because you’re the most interesting thing he’s encountered in a while? Because he attracts boring stuff to him like lint? Because he’s just regular, doesn’t seem to need you, and who cares how his dull story winds up anyway? Seems to be functioning alright? And maybe he can’t tell the difference between fabulous you and some dull Betty with half as many ideas in her head?

We’ve just described a regular, healthy human being, that’s all. Do we know what it’s like to spend lots of time with him? We don’t know a thing about that — BUT THAT’S WHAT WE CARE ABOUT. Not his creepy eyes. Not his haunted soliloquies. No. Is he relaxing to be around? Does he listen really closely to you, plus he’s hilariously funny when he doesn’t feel put on the spot, plus he’s sexy when you’re not sitting in hard chairs, talking about your careers, for fuck’s sake?

Maybe your conversations will become richer and richer. Maybe he has complex thoughts about lots of stuff, you just don’t know it yet. Maybe not, but maybe.

Keep in mind: The good guys generally don’t present all that well. They usually seem boring at first. They are not intense, they don’t need you, they don’t insult you, they don’t stare deeply into your eyes, they don’t say provocative insane shit that confuses you. Why? BECAUSE THEY ARE NOT INSANE.

My husband, for example, is the single worst storyteller in the history of the world. It’s incredible, listening to him tell a story, how clueless he is about keeping people interested. He will give you deep background information on minor characters in his story, as if his goal is to put you into a trance. He will back up and tell you which (totally irrelevant) events brought him to this (also totally trivial) tale. Here’s my husband, recalling his experiences selling encyclopedias door to door (that’s the internet, stuffed into some books. They used to sell that shit to suckers). Keep in mind, he’s talking to A ROOM FULL OF PEOPLE AT A PARTY:

Husband: So I knocked. This woman answers the door, and she says, “No thanks, not interested.” So, go to the next house. I knock. A guy comes to the door and he says, “No thanks.” So I go to the next house and knock.

Guess what happens next? Someone else says no thanks. It’s actually a little bit like performance art, what he does. And it’s transfixing, watching people’s faces transform from engaged and interested to glazed over, like human lava lamps.

But let’s be honest. People still like my husband way better than me, with my lightning-fast awesome stories. He’s less repugnant and repellent than me, of course. Who isn’t? And he’s very interesting to speak to, as long as he’s not telling a story. In conversation, he theorizes, analyzes, debates. He thinks things over and responds. And he talks about his day, and it’s generally interesting, as long as no part of his brain says “HEY THIS IS A STORY I’M TELLING A STORY NOW.”

I think my big point here is that ALL men are kind of weird mutant life forms who have giant blind spots somewhere, or they just flat out can’t function at all. You need to look out for a guy who CAN function reasonably well, is maybe just SOMETIMES depressed (Because, hello, who’s not depressed ever? Dumb people, and dumb animals. Even smart animals are depressed a lot of the time). Your ideal guy will be wonderful in almost every way, and a little screwy in one or two ways that don’t prevent him from, say, making a fucking plan a few days in advance, or staying at a party past the point where it’s 100% optimal for him to be there.

How will you find your guy? By suspending your disbelief a little longer. By going on second dates. By keeping an open mind.

I’m trying to tell you that intellectual does not have to mean tortured. If you find someone smart enough, that in and of itself is a gift that keeps on giving. He doesn’t have to be insane or intense or even wildly romantic. He just needs to be capable of intelligent discourse. Listen, think, respond intelligently. It sounds so simple, but CHRIST ALMIGHTY there are lots of dopes who don’t understand simple conversational language. And there are there lots of guys squidding around out there, spewing out inky vagaries, matching their surroundings perfectly but never fucking listening for half a second! Talk about boring.

Now, sure, your guy will need to be sensitive, with some possible emotional neglect in his past. It’s like salt: A little neglect, but not too much! It’s true though that a sliver of damage makes men more interesting. Without any damage or any sensitivity or any depressy or anxious tendencies, even smart men can sound like dumb animals.

You can take or leave a small bit of damage-spice. Overall, though, you are on the lookout for robust mental health, which often looks really boring at the outset. Likewise, men who look shiny and exciting from the very first moment are often pretty fucked and scary in the long run.

Ladies of the universe, heed me: Robust mental health and brains, paired with a great sense of humor, lots of ideas and opinions, and an ability to listen, all rolled into the form of a productive member of society? It might look dull at first because it has a bad haircut and doesn’t know how to dress, but THAT is still what you want. You don’t need slouchy romantic thinkers, OK? Those guys feel like they deserve to have an affair. They feel like they should take a year off to travel, even though the baby is still young. They feel like you’re holding them back, making things all dreary and lame in their lives. “Why can’t you happier?” they’ll ask you, sounding very unhappy themselves.

At the very least, when you encounter a squid boy, a throw pillow guy, a plastic bag man, don’t listen to his critiques of you. Just put down the throw pillow (don’t throw it!) and move on. When you believe that he’s right, that there’s something missing IN YOU, that YOU are the wound? You stay obsessed with him, and you can’t move on. TOBIA, do you still suspect that Mr. Plastic Bag had you pegged? That he’s somehow better than you because he rejected you? Because you’ll be ignoring great guys forever and ever if you truly believe that.

Look very closely at the stories you tell yourself about yourself. Then resolve to tell better stories. You ARE an optimistic fairy princess. It’s time to give some of these so-called frogs a fighting chance.


Do you ever feel like a plastic bag drifting through the wind, want to start again? Write to Polly and tell her all about it, Katy.

Heather Havrilesky (aka Polly Esther) is The Awl’s existential advice columnist. She’s also a regular contributor to The New York Times Magazine, and is the author of the memoir Disaster Preparedness (Riverhead 2011). She blogs here about scratchy pants, personality disorders, and aged cheeses. Image from a photo by James Alby.