Our Top Ten Literary Cheaters


Valentine’s Day is still days away, but we’re already growing nauseous from the saccharine sweet candy hearts, over-sized cards, and plush animals lurking every which way we turn. Puppy love is overrated. We prefer lying, plotting, and scheming drama — at least when it comes to fictional romance.

Whether your V-Day plans involve romantic candlelight or Voodoo pins, we think you’ll enjoy our top ten list of literary cheaters. These fictional guys and girls have gotten away with everything from murder to statutory rape, yet oddly enough, have still felt the love from our back pocket.

1. Odysseus of Homer’s The Odyssey (630 B.C.) Does it still count as cheating if you’ve been imprisoned into a life of luxury by a sea nymph named Calypso? We’d wager Odysseus’ long-suffering wife Penelope (who somehow managed to keep 108 various suitors at bay while her husband was gone for 20 years) would say yes. And his two out-of-wedlock kids with Calypso, Nausithous and Nausinous, would certainly back her up.

2. Gertrude of William Shakespeare’s Hamlet (1600)

Gertrude, the Queen of Denmark, is a hot mess. After the murder of her husband, she marries his brother Claudius (said murderer). On top of that, she is accidentally poisoned by Claudius. The woman is surrounded by schemes. The epic play leaves room for more questions than answers, so we never know for sure whether Gertrude was hooking up with Claudius before her husband’s death. Our bet? All signs point to yes.

3. Edward Rochester of Charlotte Bronte’s Jane Eyre (1847) Oh, Rochester. Just because you neglect your mentally unstable wife Bertha and keep her locked in the attic, that does not mean you are a single man. In fact, after reading Wide Sargasso Sea, we kind of think that you’re a dick.

4. Edna Pontellier of Kate Chopin’s The Awakening (1899) Between vacationing in Mexico and living in New Orleans, Edna is awakened to her marital frustration. She quickly realizes her budding sexuality as witnessed by both Robert and Alcee. Yep, she means business.

5. Clarissa Dalloway of Virginia Woolf’s Mrs. Dalloway (1925)

High society Brit, Clarissa Dalloway, is seemingly concerned with the frivolities of life — fashion, flowers, and parties. But we learn there is much more to this composed woman than meets the eye. Having chosen the aristocracy of a life with Richard Dalloway over former flame Peter Walsh, it is clear that Clarissa’s heart does not flutter between just these two men. While romantically tied to Peter 34 years prior, Clarissa shared an intimate kiss with Sally Setton, and continued to consider the forbidden liplock the most passionate moment of her life.

6. Tom Buchanan of F. Scott Fitzgerald’s The Great Gatsby (1925)

Tom Buchanan is quite a catch — that is, if you’re into arrogance, hypocrisy and sexism. Oh yeah, he’s wealthy, too. That’s certainly why beautiful (but meek) Daisy married him. But Daisy, one of the most desired women, is not enough for Tom, and he quickly engages in an affair with the more earthy Myrtle Wilson. Oh Gatsby, if only you would rescue Daisy — then we could add her to our list, too.

7. John Proctor of Arthur Miller’s The Crucible (1953) Other than John Proctor’s adulterous liaison with Abigail Williams in the barn, Proctor is a perfectly good man. He is honest, kind, and hard working. But Abigail’s jealousy of Elizabeth Proctor leads to a witchcraft hysteria, and ultimately, John is hung for his one veer from purity and goodness.

8. Sheba Hart of Zoe Heller’s Notes on a Scandal (2003) Sheba Hart has many attachments. She is married with two children, but her ties don’t end there. At 41, she engages in an affair with one of her students, 15-year-old (and we assume, very cute) Steven Connolly. But it is not only Mr. Hart who is being cheated on, as Sheba’s (crazy) friend and co-worker, Barbara Covett becomes jealous of the depraved relationship, and things quickly spiral out of control.

9. Todd and Sarah in Tom Perrotta’s Little Children (2004) Todd’s long-legged wife and Sarah’s porn-addicted husband get cast aside during a summer of sandboxes, red bathing suits, and sticky lemonades. We can’t help but root for this pair — their spouses suck, their kids can play together, and well, they can, too.

10. Howard Belsey of Zadie Smith’s On Beauty (2005)

Art history professor Howard Belsey seems to create havoc wherever he goes. First, he causes familial disgrace when he cheats on his wife (of 30 years!) with a family friend and fellow professor. But don’t be silly — it doesn’t stop there. Next, Howard has an affair with college student Victoria, who happens to have been involved with his 20-year-old son, Jerome. Oh, Howard, you’ve caught yourself in quite the tangled web.

Who would you add to our list?