The 7 Worst Wingmen in Literature

Say you’re going out for a night on the town, and romance is on your brain. You’d be wise to bring along a character who can break the ice, talk you up, and be an overall awesome wingman. Here’s a great list of some bros you might want to consider in your quest for love—but you should also know which characters to avoid. That’s why we put together this cautionary post about the worst wingmen in literature—guys who will stab you in the back, scare off your date, or just straight-up steal the affections of anyone who looks your way. Beware!
1. Iago of Shakespeare’s “Othello”
If your supposed BFF is secretly plotting an epic downward spiral tailored just for you, it’s probably time to dump him. Iago hates Othello’s guts, but instead of being a man about it, he gaslights his master into believing his wife is unfaithful. Iago is such a butthead that he can’t even own up to his own treachery, simply saying, “Demand me nothing” as his defense. Watch out for this slippery schemer; he is nothing but trouble.
2. Lord Byron’s Don Juan
On the surface, the legendary Don Juan might seem to be the perfect wingman. He is the king of flirtation, and his magnetism could be useful for getting new people to your table. The only problem is that practically anyone who sees Don Juan falls for him. This Spanish seducer might try to have your back, but ultimately, he’d end up having your crushes on their backs.
3. Pangloss of Voltaire’s Candide
Talk about setting yourself up to fail. Pangloss is Candide’s esteemed tutor in Voltaire’s beloved satire, and professes the philosophy that “all is best in the best of all possible worlds.” Meanwhile, the guy is a total lightning rod for disaster, and misfortune follows Candide everywhere he goes as he attempts to square reality with Pangloss’ lofty teachings. Don’t take this tutor out on the town with you—who knows what kind of epic fail might result.
4. Heathcliff of Emily Bronte’s Wuthering Heights
Can you imagine how awful a night out with Heathcliff would be? His tortured soul would completely bum out anyone within 10-mile radius, and he’s a rude jerkbrain to boot. On top of all that, he’s broodingly handsome, so any potential dates that dare to approach your table would be locked into the kind of ungodly obsession this nutcase so casually inspires. Leave him to Cathy; those maniacs deserve each other.
5. Holden Caulfield of J.D. Salinger’s The Catcher in the Rye
Unless you date people who love being told that they are phonies every five seconds, avoid Holden Caulfield. Enough said.
6. Puck of Shakespeare’s A Midsummer Night’s Dream
It’s bad enough that Puck’s whole strategy as Oberon’s wingman is doping innocent people with love potion—dude, not cool. However, on top of that, Puck invariably messes up which errant lover is supposed to be drugged with fairy-juice, and whom they are supposed to to fall for upon awakening. Sure, it makes for a hilarious adventure on stage, but you’d hardly want this mischievous sprite backing you up at a bar.
7. Gideon Graves of the Scott Pilgrim series
If you like the same girl as Gideon Graves, you better be willing to fight for her. No, we mean, really, really fight for her: with ninja stars, magic hammers, katanas, and loud music. Gideon Graves is the worst wingman in the world of comics, a guy so romantically selfish that he made an entire league of evil exes just to control one pretty lady’s love life. Steer clear!
Who do you think is the worst wingman in literature?