It’s Complicated: 8 of the Most Frustrating Relationships in Literature

There are only three reasons you might purposely select the “it’s complicated” status on your Facebook page:

1) You also control the page for a famous dead person like Søren Kierkegaard and intend to link the two for a laugh

2) You don’t have an official boyfriend or girlfriend but would still like people to know you’re getting some action

3) Your romantic situation truly is a mess, and until there’s a relationship setting for “soap opera,” the word “complicated” will have to do

Those of us in group three might be at our wits’ end, but literarily speaking, at least we’re in good company.

Here to remind you that things could always be worse are eight of the most complicated relationships in Western literature.

1.  Arthur Miller’s The Crucible

Year Produced: 1953

The Couple: John and Elizabeth Proctor

The Problem: Abigail Williams

John and Elizabeth Proctor have differences like any couple, but when push comes to shove, the two can count on a solid foundation of mutual respect. So when Abigail Williams gets Elizabeth in trouble with the law, John stops at nothing to protect his wife.

Two things we should probably mention: 1) Abigail uses a hand-stitched voodoo doll to frame Elizabeth for witchcraft. This ain’t exactly the 17th-century equivalent of a parking violation. 2) John is probably the teensiest bit motivated by guilt. After all, he did indulge in a brief affair with Abigail some months ago and is very aware of Abigail and Elizabeth’s mutual hatred.

The only real leverage John has against Abigail is to confess the secret of their relationship publicly, which goes a long way in discrediting her, but isn’t exactly high on the list of things he planned to do that weekend. To test John’s claim, the judge brings Elizabeth into court to ask if her husband is a lecher.

Despite her incredible anger over the affair, Elizabeth chooses this particular moment to cover for her husband, meaning that she and her husband will now spend some quality time in prison while they both wait to be executed. Arthur Miller, we believe the word you are looking for is “fail.”

2.  F. Scott Fitzgerald’s “The Curious Case of Benjamin Button

Year Published: 1922

The Couple: Benjamin Button and Hildegarde Moncrief

The Problem: Father Time

If you ever meet a man who ages backwards, you should probably scratch out a serious pros and cons list before deciding to pursue a relationship with him. Especially if you’re into older guys.

Benjamin Button is born looking about seventy years old and gets younger with time. When he is around twenty (i.e., looks fifty), he meets and marries the beautiful young Hildegarde Moncrief, who would “rather marry a man of fifty and be taken care of than many a man of thirty and take care of him.” Boy is she barking up the wrong tree.

For whatever incredibly short-sighted reason, the two have a child together, but as Benjamin becomes younger and more vigorous, he gradually gets bored with his aging wife. The two go their separate ways and by the time Hildegarde reaches the hot cougar stage, Benjamin has acne and a voice like a squeaky door.

The only way he can fit in at family reunions is by calling his own son “Uncle,” and before long, he’s being set up on playdates. With his own grandson. Moral of the story: the age thing can make or break a relationship – regardless of what Harold and Maude would have you believe.

3.  T.S. Eliot’s “The Love Song of J. Alfred Prufrock

Year Published: 1915

The Couple: J. Alfred Prufrock and a mysterious, shawled woman

The Problem: J. Alfred Prufrock

Prufrock’s exact relationship to the mysterious, shawled woman is complicated to say the least. First of all, he fails to give her so much as a name and usually alludes to her in only the most cryptic terms possible: a braceleted arm, a trailing skirt, the scent of perfume… by the end of the poem, he’s going on about mermaids decked out in seaweed and the metaphorical possibility of drowning. We imagine Freud would have a thing or two to say about this.

Second, Prufrock seems spends a good portion of his rambling “love song” trying to psych himself up to approach the woman – only to then decide that he’s better off dying alone as a friendless, bald-headed man who apparently has a lot invested in whether or not he rolls up the bottoms of his pant legs. TMI, Prufrock, TMI.

On top of all this, Prufrock is so deep in his own head that the reader is never sure where he actually is or what he’s doing there. Is he wandering through a dodgy part of town at night and fantasizing about parties spent with his ladylove? Is he at such a party reminiscing about all those meandering, late-night walks? Does he actually approach the woman before losing his nerve or is the entire nerve-losing scenario simply imagined? Is there even a shawled woman?? We just hope Prufrock never finds himself in a situation where he has to give any eyewitness accounts to the police.

4.  Nathaniel Hawthorne’s The Scarlet Letter

Year Published: 1850

The Couple: Hester Prynne and Arthur Dimmesdale

The Problem: Roger Chillingworth and the watchful eye of God

If you think having a baby in prison is bad, try doing it in 17th-century Puritan New England – when your husband hasn’t been seen in two years. This is exactly what Hester Prynne does, only instead of trying to make the situation easier for herself, she also vows to keep the identity of her baby-daddy a secret. In case anyone forgets just how humiliating this entire ordeal is, Hester is forced to wear a scarlet “A” for “adulterer” on her dress at all times.

Just when life can’t seem to get any worse, Hester’s long-lost husband turns up calling himself “Roger Chillingworth.” Jumping on the secret identity bandwagon, Chillingworth gets Hester to keep his real name secret before deciding to spend lots of quality time around the local reverend, Arthur Dimmesdale. With time, Chillingworth gains the reverend’s trust and figures out that the guy also happens to be – oh snap! – Hester’s man on the side.

Despite their temptation to run away together, Hester and Dimmesdale righteously agree to stay in Boston for a second helping of that good ol’ social condemnation. Eventually, the reverend confesses his crime: in a move that would have made Matthew McConaughey proud, Dimmesdale bares his chest before the whole town, revealing a giant red “A” that he has carved into his flesh as either sign of solidarity or a kickass precursor to the matching tattoo. Dimmesdale then dies, ensuring that Hester never gets any help with that whole kid thing.

5.  Charlotte Brontë’s Jane Eyre

Year Published: 1847

The Couple: Edward Rochester and Jane Eyre

The Problem: Bertha Mason, social convention, and a rather twisted sense of humor

Master-servant romances were tricky things back in the 1800s. Exploitative at worst and frowned upon at best, they almost never succeeded in making the concerned parties happy. And yet, despite all the pre-existing obstacles, Edward Rochester actually goes out of his way to make life hell for Jane, his (unknowingly) beloved servant.

First, he leads her on, then he pretends to be slated to marry another (far more beautiful) woman, and finally he threatens to boot her off his estate. Only when heartbroken Jane decides to leave the country does Rochester admit that he’s madly in love and has been toying with her the whole time. All is forgiven and before long, the two agree to get hitched.

This would be a great time for Rochester to mention Bertha Mason, the crazy woman locked in his attic.

But no – this juicy tidbit instead comes out three-quarters of the way through the couple’s hasty wedding ceremony. In fact, it turns out that Rochester is actually already married to said crazy woman, turning his almost-wedding with Jane into an almost-affair.  Although the two do manage to work things out in the end, it’s only after a devastating fire, a suicide, some crazed wandering through the moors, a painful disability, and the miraculous appearance of a rather large sum of money.

6.  William Shakespeare’s Hamlet

Year Written: circa 1600

The Couple: Hamlet and Ophelia

The Problem: Polonius and them existential blues

Shakespeare’s Hamlet opens with the young prince discovering that his deceased father was murdered by his father’s own brother, meaning that by the time Polonius comes onto the scene to prevent his daughter, Ophelia, from seeing Hamlet anymore, the prince is already having a pretty bad day.

From here on out, Hamlet never misses a chance to say something truly offensive to his ex, which could either mean that a) he’s truly hurt by the breakup; b) he never loved her to begin with; c) he’s really unstable; or d) it’s all for show because he’s only pretending to have lost his mind.

To be fair, however, Hamlet and Ophelia’s relationship is plenty complicated long before Polonius intervenes. The romance takes place almost entirely before the play starts, meaning by the time everyone is introduced, Hamlet’s mourning for his father makes it impossible to get a read on the couple’s dynamic. And by “get a read on the couple’s dynamic,” we of course mean “figure out whether or not they’ve slept together,” which would have made Ophelia damaged (and probably pretty bitter) goods back in the day.

Oh yeah, and then there’s that whole thing where Hamlet accidentally murders Polonius but seems not to care, driving Ophelia crazy to the point where she (probably) commits suicide by covering herself with flowers and jumping into a stream. Let’s not even get into what happens when her brother defends her honor by challenging Hamlet to a duel…

7.  Geoffrey Chaucer’s “The Miller’s Tale” from The Canterbury Tales

Year Written: circa 1400

The Couple: John and Alisoun

The Problem: Nicholas, Absolon, and the apocalypse

Although John isn’t the most inspiring husband in literature, he appears to be a decent, considerate kind of guy. Which is why we can’t help but feel sorry for him when Nicholas and Absolon begin trying to bed his wife.

Admittedly, Alisoun is much younger than John and probably not his best match, so we’re not exactly surprised when she begins sleeping with Nicholas, the young scholar. The lovers cross the line, however, when they tell John to hurry into the attic (and more importantly, out of the bedroom) because – get this – God is flooding the world on that particular night.

Enter Absolon, the lecherous parish priest who also tries to woo Alisoun. Do we feel sorry for him when, closing his eyes and attempting to kiss the lady through the window, he ends up with a faceful of her buttocks? Not particularly. Do we feel sorry for Nicholas when, thinking he’ll repeat the prank, he sticks his butt out the window and ends up with a hot poker between his cheeks? A little. But nothing tugs at our heartstrings more than when John comes crashing down through his own house in a makeshift bathtub-ark only to discover that a) the land is dry as ever; b) his wife is having an affair; and c) the entire village thinks the situation is a real knee-slapper.

8.  Homer’s Odyssey

Year Written: circa 700 BCE

The Couple: Odysseus and Penelope

The Problem: Poseidon, Polyphemos, the Laestrygonians, Circe, the Sirens, the Scylla, the Charybdis, Calypso, over 100 eager suitors

If you think that having a long-distance relationship is complicated in the 21st century, imagine pulling it off around the twelfth. BCE. This is what Odysseus and his wife, Penelope, manage to do in what has got to be the most frustrating relationship of all time.

After fighting in the Trojan War for a straight decade, Odysseus spends another ten years struggling to sail home. (Note to self: don’t piss off the god of the ocean right before any major maritime endeavors.) While he’s at it, Odysseus battles monsters, sorcerers, treacherous seas, and a crippling case of get-there-itis.

To be fair, however, at least Odysseus has adventure to distract him – not to mention some seriously hot flings along the way. Penelope, on the other hand, spends the entire twenty years raising their son and resisting the advances of 108 of antiquity’s most annoying bachelors. Her favorite pastime? Weaving a death shroud for her father-in-law. At least nowadays we have sexting.

13 thoughts on “It’s Complicated: 8 of the Most Frustrating Relationships in Literature

  1. Casey says:

    Great list. I am going to try and think of some more.

    How about Neal Cassady and every woman he came into contact with in all of Jack Kerouac’s novels?

  2. anardev says:

    Oh come on, Catherine and Heathcliff should be at the top of this list. They bring death and destruction upon three generations of their families and themselves.

  3. Alexa says:

    I think anardev is right, Catherine and Heathcliff are the royal couple of complicated relationships – what could be more messed up than a “relationship” in which one has to dig up the corpse of the other to finally get close to her, after having completely destroyed the lives of at least nine people, themselves included?

  4. Jyoti says:

    Its Catherine and Heathcliff..and their strange, passionate and the most complicated love story of all times..

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