The 10 Worst Boyfriends In High School Literature

1. Holden Caulfield, The Catcher In The Rye

It’s probably way too easy to pick on a kid who is just really tormented by his brother’s passing — and with good reason; if you ever have a chance to read ‘The Ocean Full Of Bowling Balls,’ Allie’s death was pretty bleak — but not only does Holden lose interest during his date with Sally Hayes, but he totally botches one of the most cringe-worthy experiences with a prostitute any literary teenage runaway has ever experienced. He’s angsty, he’s rude — and yes, he’s a teenager, but this is the dude that would probably just laugh as you’re trying to beat down the wall to get yourself into his heart. He’d probably also blame you for any little thing you “made” him do. Really, he’s a headache and a half, and though it’s probably safe to say that every girl has one of these guys in her past, that’s just a cross we have to bear in the name of adoescence.

That’s the thing about girls. Every time they do something pretty, even if they’re not much to look at, or even if they’re sort of stupid, you fall in love with them, and then you never know where the hell you are. Girls. Jesus Christ. They can drive you crazy. They really can.

2. Oedipus, Oedipus Rex

If you’re going to date Oeddie, you should know that between all of the abandoned-as-a-child issues, the regal complex, the killing-his-dad complex, and the, er, mother of all mommy issues, this is the fixer-upper kind of dude your friends warn you about. He’s too broken, they say. He’s got too much baggage! But he’s so cute, you think to yourself, and oh, how you long to change him. He’s also the kind of guy who would spend all day long chastising you, only to find out he’s been a hypocrite, and would then endlessly self-flagellate to earn your forgiveness. Nobody needs that sort of pressure. (Not to mention the fact that if you’re dating Oedipus, you’re probably dating your own kid.)

3. Odysseus, The Odyssey

[youtube http://www.youtube.com/watch?v=I6azzNTr6xE&w=584&h=390%5D

We’re going to ignore whatever tragic treatment they did to the majesty of the song in this video, but here’s a modern-day retelling of The Odyssey for you: your boyfriend goes out to the club all night long with his bros (or, you know, spends 10 years fighting the Trojans in a very, very bleak war) only to call you last minute and let you know that he’s going to keep the night going (or he pisses off a god or two so now he has to spend another 10 years getting home.) On the way, he gets into a whole lot of trouble, might cheat on you here and there, swears he didn’t do a thing, and then expects you to welcome him home with open arms just because he knows you found sleeping alone to be torture.

Also, the Boys of Backstreet are totally the Homers of our generations. Those songs are going to hold up for all of eternity.

4. Jay Gatsby, The Great Gatsby

I do feel like I have to admit that I have a Great Gatsby quote tattoo, because this is one of my favorite books of all time, but really, Gatsby did not know how to let a girl go. Daisy Buchanan married another man, had a kid by him, and beyond that, was a pretty terrible human being. (Fitzgerald uses the term “careless” to describe the Buchanans, and it’s pretty freaking apt.) Still, James Gatz is so besotted with this girl who he believes to be out of his league and on a pedestal that he literally builds an entire empire (and, y’know, breaks a few laws) in order to win her back. And then he dies for her, and she doesn’t care. If you’re going to break up with your boyfriend because he conveniently gets murdered by your husband’s dead mistress’ husband, that’s kiiind of a lot to have on your conscience.

(And because we have now entered the Leonardo DiCaprio-invades-9th-grade-lit portion of the program…)

5. Romeo Montague, Romeo & Juliet

Yes, I get it, ’til death do us part, hopelessly, crazy, drunk in love, that’s all well and good. It’s cute, really, if you’re really going to go all Anna-in-Frozen and decide you love a guy five seconds after meeting him. See, the thing is, Romeo is meant to be a bit of a farce. He’s based off this dude named Petrarch, who spent his whole life writing very public, very popular sonnets to this woman he saw one day who was married, never returned his advances, and to whom he’d never spoken a single word. Shakespeare, a poet in his own merit, had it up to here with lovestruck dudes running around and copying Petrarch’s style — along with codpieces, being a Petrachan lover was like Elizabethan England’s version of a hipster. So good old Billy Shakes (whoever he is) goes and funnels this into Romeo’s infatuation with Rosaline  — remember her? — in the beginning of the play, and the fact that our starcrossed lover just drops her like last week’s Malaysian plane conspiracy theory is a pretty crappy thing to do. Minus the whole Both Being Dead thing, why don’t you think he’s going to do the same thing to you, Juliet? Save yourself, girl! You don’t have to die for him! Clueless-era Paul Ru— I mean, Paris is not a bad consolation prize!

6. Tom Sawyer, Adventures Of Tom Sawyer

Tom is the kind of boyfriend who would find it funny that you ate it at the bar. He’d make fun of you mercilessly, and not in that cruel-to-be-kind sort of way, but because he is clueless enough to not realize that yeah, it kind of hurts your feelings. As a modern-day allegory, Tom is totally The Office‘s Roy Anderson, when you know in your heart of hearts that you’re supposed to end up with the #kanyeshrugging Jim Halpert. Really, he would forget that you went to the bathroom and leave you at a minor league hockey game. (Tom Sawyer would also end up with a better life and a $50,000 sports car after you left him, because that’s just the way Mark Twain, NBC sitcoms, and life work.)

7. Heathcliff, Wuthering Heights

Heathcliff is totally that boy who was best friends with you all throughout elementary school, threw a fit that you developed a mild crush on the popular boy in school because he wanted you for himself like you were his favorite toy, convinced his mom to let him go to a different high school under the guise of a broken heart, and then wound up at the same college as you, all newly buff and attractive, and then proceeded to torment you for the rest of forever, citing your crush on the popular boy as the catalyst and that this was “all your fault.” (… What, you didn’t have a friend like that? I digress.) The whole concept of our souls being made of the same stuff is romantic, to be sure, but Bronte’s work harkens back to the theme of people who just don’t know how to let lost love go.

Though, for full disclosure: someone once pointed out the parallels to Heathcliff’s abuse of the next generation of Earnshaw and Linton kids, and Severus Snape’s abuse of Harry Potter, child of the unrequited love of his life, and I haven’t been able to look at either character the same way since.

Why did you betray your own heart Cathy? I have not one word of comfort. You deserve this. You have killed yourself. … You loved me – then what right had you to leave me? Because … nothing God or satan could inflict would have parted us, you, of you own will, did it. I have not broken your heart – you have broken it; and in breaking it, you have broken mine. So much the worse for me that I am strong. Do I want to live? What kind of living will it be when you – oh God! would you like to live with your soul in the grave? […] I forgive what you have done to me. I love my murderer – but yours! How can I?

8. Stanley Kowalski, A Streetcar Named Desire

The boyfriend who is the reason why the word “boy” is part of the compound, Stanley Kowalski is Citizen Number One when it comes to literary characters you fell in love with because you thought their on-screen counterparts were hot. (And to be sure, Brando was goooood in that movie.) But without Brando’s scruffy, loveable, bad-boy sheen to distract you, Kowalski is a bit of a brute on his own, heightened by the fact that he is so easily antagonized by the wilted flower known as Blanche Dubois. It doesn’t take a lot for Stanley to get riled up, and the famed Stelllaaaaaaaaaa! has to do a lot of babysitting to keep her husband’s temper down. (But then again, they’re having a baby together, so maybe this is his master plan in giving her some practice. I don’t know. I really love vintage Marlon Brando.)

9. Othello

Where to begin with Othello, the Moor, tormented hero, probably suffering from a fair share of PTSD, hopelessly devoted to a girl he’s like 95% sure cheated on him just because his double-crossing frenemy said so… oh. Wait. Really, all of Shakespeare’s work is riddled with really bad boyfriends, which probably has something to do with the fact that he left Anne Hathaway (no, the other one) at home with their children while he was chasing his dream in London — and left her only the second-best bed when he died. Really.

But the fact that Othello is willing to kill his wife because he thinks she cheated on him is pretty high up there on the bad-boyfriend-o-meter on its own.

10. Mr. Rochester, Jane Eyre

Sure, it’s bad that he baits Jane into confessing that she loves him first by dangling his attachment to another woman in front of her face like a diamond ring just out of reach, the carrot to Jane’s poor, lovestruck rabbit. But what’s really egregious here is that the man kept the “ex”-wife whose crazy guts he couldn’t stand locked up in the highest room of the tallest tower of his manor house WHILE he’s romancing Jane. Like, in what part of your idealistic little governess brain is this a good idea? Nowhere, that’s where. Girl, take that paycheck and get gone.