If You Met These Literary Characters on OkCupid

If you think about it, reading classic literature and dating online are actually pretty similar activities: there's the thrilling promise of great revelation, great passion, or even great personal transformation present in both pursuits — and that great potential makes you willing to put up with whatever else comes up along the way, even if it's hours and hours of listening to someone drone about how to extract oil out of whale carcasses, or his boring finance job, or whatever.

Another element that classic literature shares in common with online dating is that both are chock full of egomaniacs, self-involved tools, complete d-bags, and other assorted assholes you'd never want to actually have a cup of coffee with. But unlike the jerks of OkCupid, the rankest dillwanks of the Western cannon remain safely secured inside their sexy, sexy books, unable to send you badgering messages about meeting up this Friday, gross unsolicited sexual fantasies, or random requests for nudes. But... what if they could?!

We probed the least dateable minds of classic literature, and came up with the nine worst online dating messages this side of your freshman English seminar — messages so bad, they might inspire you to feel a little bit better about your own online dating life. Hey, at least that weird guy from your last OkCupid date who refused to take his soiled parka off the entire night didn't ask you where the ducks go in the winter, right?

Heathcliff (from Wuthering Heights by Emily Bronte) on Craigslist

Hey there,

I saw your "Missed Connection" ad from the other day, and thought you might have been talking about me, so I wanted to get in touch. I was, as you noted in your ad, a tall, Caucasian, dark-haired male wearing a vest and brooding softly on the Times Square-bound 7 train. You said I killed you--haunt me then. The murdered do haunt their murderers. I believe--I know that ghosts have wandered the earth. Be with me always--take any form--drive me mad. Only do not leave me in this abyss, where I cannot find you! Oh, God! It is unutterable! I cannot live without my life! I cannot live without my soul! Anyway, hit me up if you want to get Thai food some time, you sound cool.

roger chillingworth (from The scarlet letter by Nathaniel Hawthorne) on Tinder





Daisy Buchanan (from The Great Gatsby by F. Scott Fitzgerald) on Ashley Madison


i don't usually like to be 2 forward, but i looked at your profile and totally thought we should talk. i think we have so much in common!! alo you seem rich and i think that is AWESOME!!!!! LOL but srsly ur shirt is so cool. write back!!!!!!! LOL <3 ;)

Hamlet (from Hamlet by William Shakespeare) on Tinder

-It's so embarrassing to be on here, right?


So when I saw that we got paired up through Stradlater, at first I said to myself, "Forget about this girl. She's a phony like the rest of them." But then I saw all those pictures from your year abroad in Paris, and you looked so happy to be in all those old buildings, just smiling in some library for chrissake like it was the goddamn fourth of July. And all of a sudden, I felt pretty lousy. I thought, "Maybe this girl thinks Stradlater is a goddamn stupid moron, too. Maybe also just accepted his friend request because he acts like such a goddamn prince of a guy if you don't." If you don't think I'm talking crazy, message me back and maybe we can meet up some time — I can usually get a day pass on the weekend.

Sal Paradise (from On the Road by Jack Kerouac) on OkCupid

Hey I saw that you're looking for a steadily employed non-drinker who loves dogs Asian fusion cooking and the NHL awwwwww I am none of those things but when I looked at your picture, everything felt so holy, I felt like a new man and then a pain stabbed in my heart, the way it does every time I saw a girl I thought was hot who was going for an employed non-drinking dog lover in this too-big world. Wait, which one are you in the picture? The blonde one?

Count Vronksy (from Anna Karenina by Leo Tolstoy) on HowAboutWe

Hey shawty,

You're gorgeous. How about we dim the lights, pop some Cristal, put on a little Avicii, and see what happens?

bertha dorset (from House of Mirth by Edith Wharton) on Ashley Madison


I've got a ton of money and about three hours free next Monday afternoon. Write back before I change my mind.

Tom Buchanan (from The Great Gatsby by F. Scott Fitzgerald) on OkCupid

what up

[photo of his penis]

Images: M2K Productions, Giphy, Wiffle Gif