Book boyfriends are always a fun topic, but what about the guys that just don’t make the cut? See which fictional men make the worst boyfriends from modern and historical fiction.

Wuthering Heights

Heathcliff is the ultimate anti-hero. You want to like him, you want him to be more than he ever could be for Catherine and for himself. Readers want to believe his cruelty is merely an expression of his frustrated love for Catherine, or that his sinister behaviors serve to conceal the heart of a romantic hero. Sadly, this is not the case.

Heathcliff and Catherine are both terrible people. Neither does anything to deserve love that they harbor for each other. But Heathcliff goes above and beyond in his treatment of Isabelle.

Heathcliff seized, and thrust Isabella from the room; and returned muttering – “I have no pity! I have no pity! The more the worms writhe, the more I yearn to crush out their entrails! It is a moral teething; and I grind with greater energy in proportion to the increase of pain.”

Fifty Shades of Grey

Does this one require an explanation? Okay, fine. He’s abusive, emotionally fragile, angry, violent, and secretive just to mention a few things. Then there is his penchant for buying up companies just so his kind-of-girlfriend can have a job that he can control. There is nothing sexy about that kind of control.

“Well, if you were mine, you wouldn’t be able to sit down for a week after the stunt you pulled yesterday. You didn’t eat, you got drunk, you put yourself at risk.”

And that about sums it up.

Catcher in the Rye

Holden Caulfield is not a lovable character in any way. Negative doesn’t begin to explain his view on life. He dislikes movies, money, and talking about his childhood. His angst, anger, and self-imposed alienation make him the original loner. All of these things don’t necessarily make him a terrible boyfriend, but his feelings towards girls kind of seals the deal.

“I mean most girls are so dumb and all. After you neck them for a while, you can really watch them losing their brains. You take a girl when she really gets passionate, she just hasn’t any brains.”

Oh, Holden, you sweet talker.

Twilight

Edward Cullen definitely improved with age, but in the beginning he had some extremely creepy tendencies. Stalking Bella while she slept was just the first step in their obsession-driven romance. Not to mention he used sex to emotionally blackmail Bella into marrying him.

Edward, we get that you want to wait until marriage, and that’s cool, but holding sex over someone’s head is not a good boyfriend quality. Edward is also a bit of a control freak who slashes Bella’s tires, has Alice kidnap her, and he breaks her car so she can’t visit Jacob, all under the guise of “being for her own good.” This is not the kind of guy anyone needs in their life.

Here are just a few of his loving comments:
“Bella, it’s not my fault if you are exceptionally unobservant.”
“Bella, you are utterly absurd.”

Pride and Prejudice

George Wickham may be handsome, but that isn’t enough to make up for his womanizing and gambling. Wickham uses his good looks to ingratiate himself toward the fairer sex in hopes of getting money. His first victim was the young and impressionable Georgina Darcy, but he quickly moved on to the Bennett ladies. Wickham spread lies about Darcy to suit his own purpose. Not really a stand up guy. In the end, Wickham has to marry Lydia, and to honest, it seems like a fair consequence for his behavior.

“I cannot pretend to be sorry,” said Wickham, after a short interruption, “that he or that any man should not be estimated beyond their deserts; but with him I believe it does not often happen. The world is blinded by his fortune and consequence, or frightened by his high and imposing manners, and sees him only as he chuses to be seen.”

It just reeks of bitterness.

Hush, Hush

Patch Cipriano is a bad boy who wears black and rides a motorcycle, but that’s not what makes him a bad choice as a boyfriend. Patch is actually a fallen angel who is supposed to kill Nora, for his love, in order to restore her. So he stalks Nora, tries to control her, says mean things to her, and scares her all with the intent of killing her at some point. Of course, in the end, he falls in love, but is that really enough?

“I’m not going to kill you, Nora. I don’t kill people who are important to me. And you top the list.”

Aww, doesn’t that just make you feel warm and fuzzy?

The Great Gatsby

Jay Gatsby is beyond wealthy and throws brilliant parties, but underneath it all he is incredibly flawed. Gatsby hides who he really is behind his money. His obsessive love for Daisy and delusional thoughts that money will bring him happiness make him even less appealing. To Gatsby, Daisy is a possession, something to be won. Then, of course, there is the way he obtained his wealth: through criminal activity. Gatsby may throw a killer party, but boyfriend material he is not.

“Many men had already loved Daisy—it increased her value in his eyes.”
“Her voice is full of money.”

Sa-woon… not.

Jane Eyre

Mr. Rochester from Jane Eyre is by far one of the worst choices for a boyfriend ever. First, he keeps his wife locked in the attic. Of course, he took her money for himself, moved her away from her family, and managed to sleep his way across Europe.

In case that wasn’t enough evidence, consider this: He’s rude, abrupt, always on the edge of violence, likes to order people around, and teases Jane on at least one occasion until she cries. Oh yeah, he’s a winner. Did we mention he’s totally into bigamy?

“But I don’t mean to flatter you: if you are cast in a different mould to the majority, it is no merit of yours: Nature did it.”

He says the sweetest things.

Who’s your worst book boyfriend?