7 Novels About Fuckbois and Other Messy Men

As a reader I want a deeply flawed love interest. A relationship that’s doomed from the start.

My first taste of the deeply flawed love interest was the Byronic hero. I learned about him in the classroom. I saw him in the many TV adaptations of English classics that occupied my youth. He was brooding, aloof, misunderstood. The misunderstood part was key, it meant his despicable behavior was easily forgiven. These doomed affairs were romanticized, held up as examples of great love, something to aspire to (note: I attended an all-girls school so the bar was very low/debatable whether such a bar existed at all). Fortunately, society is far less kind to this man today, and with good reason. We see them for what they are. 

As a writer, I want to create conflict in matters of the heart. My debut novel The Freedom Clause is about a young British couple, Dominic and Daphne, who open up their marriage for one night a year over a period of five years. Daphne follows the rules around this arrangement carefully, respectfully, whereas Dominic does the opposite, the freedom clause only encouraging his worst qualities to surface. 

In this reading list, the male love interests have toyed with and broken the hearts of their female counterparts. Once known as the Byronic hero, these men are fuckbois and they’ve reigned supreme in literature, and in real life, for centuries. 

Nathaniel P in Adelle Waldman’s The Love Affairs of Nathaniel P

This book so perfectly captures a particular type of man—intelligent, literary, seemingly progressive but deeply shallow—that it might be depressing to read if its tone wasn’t so sharp and witty. Nathaniel’s crimes are mostly committed in his head. He harbors unkind thoughts and feelings towards women, believing them: “capable of rational thought; they just didn’t appear to be as interested in it.” And he enjoys a sense of superiority over women: “it was not always unpleasant to deal with a hysterical woman. One feels so thoroughly righteous in comparison.” We watch Nathaniel approach dating in transactional terms (“these emails were invitations to ask her out. If he went along with it sooner or later his dick would be in her mouth.”) But if dating is indeed a transaction, Nathaniel doesn’t offer women much in return, being protective over his time, emotions, and any promise of a commitment. 

Hilariously, Nathaniel is so superficial in nature that it bothers him when he finds himself attracted to a woman who isn’t “more obviously hot” and whom one friend ranks: “a seven (coworker material).” But so long as we are ranking people, let’s agree that Nathaniel’s personality is a two, and he will never make a great partner because this f boy is your classic narcissist. 

Angel Clare in Thomas Hardy’s Tess of the D’Urbervilles 

Angel Clare is a classic “nice” guy. He keeps his hypocrisy and double standards hidden from Tess until their wedding night when Angel admits he’s not a virgin. What a relief! Tess reveals that she isn’t either (she was raped). Who wouldn’t hug Tess and tell her she is loved at this point? Angel, it transpires. Inconceivably, Angel cannot move past the news that Tess isn’t a virgin. (“You were one person; now you are another. My God—how can forgiveness meet such a grotesque—prestidigitation as that!”) It’s almost like he’s put Tess up on a pedestal from which she is bound to fall… not that Angel plans to accept culpability. He runs off to Brazil and we can only imagine what he gets up to there, caipirinha in hand. 

Modern day Angel would get dumped a lot and seem surprised by this. He would turn angry and unpleasant (think Alec Baldwin) towards any woman who rejects him. He would refuse to see a therapist until a rage incident with a female colleague for “taking too long” at the photocopier and, job in jeopardy, he would relent and go to therapy. For a long time. 

Daniel Cleaver in Helen Fielding’s Bridget Jones’s Diary

Daniel Cleaver is the colleague you must stop flirting with, entire days of productivity lost to witty emails flying back and forth between your inboxes (“You appear to have forgotten your skirt. As I think is made perfectly clear in your contract of employment, staff are expected to be fully dressed at all times”). Yes, Daniel is very charming and attractive and fun, but he’s also a situation-ship. And he cheats. And he only falls hard when a woman is firmly off the market and completely unobtainable. 

This type of f boy is everywhere. I will go one step further and say he is a rite of passage in your twenties. He is a total head fuck at the time, and an absolute marvel to reflect on a decade later, as you give a smug and self-congratulatory “look how far I’ve come” wave to your past. And you have come far, you really have. 

Heathcliff in Emily Bronte’s Wuthering Heights

Heathcliff makes the dating pool look rather bleak. If you do, against your better instincts, go on a date with this man you will notice that he’s moody, obsessive, and definitely not over his ex, Cathy. He lurks around Cathy’s home, looking threatening, and when she dies, Heathcliff decides to open up her grave to hug her, as well as destroy the lives of all those in his orbit (all completely normal behavior). 

Incredibly, Heathcliff gets married. You will stumble across his Instagram profile, years after dating him, and see he married a woman named Isabella. Immediately, you will recognize that this woman is miserable and so is Heathcliff, and things not working out between you two was the ultimate lucky escape. This two-minute analysis is bang on. Heathcliff calls his wife, Isabella, a “wicked slut” and throws a knife at her. Isabella says of Heathcliff: “I gave him my heart, and he took and pinched it to death; and flung it back at me.” 

In summary, every bad romantic move Heathcliff makes can be linked back to Cathy. Just replace “Cathy” with “art” and this is the modern-day f boy you are dealing with: the tortured artist.

Maxim de Winter in Daphne du Maurier’s Rebecca

Maxim de Winter is a hot name. And something about him gives you “controlling but it’s hot” vibes (a red flag for some but you are willing to overlook this). Maxim lives at a place called Manderley which is enormous (homes with names always are). You might be tempted, on an early date with Maxim, to daydream about dropping your own name in favor of being called Mrs. de Winter. This daydream mainly features you swanning around the estate in espadrilles and a long floaty dress, martini in hand. Except you don’t want that. The original Mrs. de Winter died in a tragic drowning. 

As you get closer to him, Maxim lets you in on a little secret: he shot Rebecca because she was pregnant with another man’s child and she refused to divorce him. He made it look like an accidental drowning. At this point, the fantasy of Manderley loses its appeal, and you remove the espadrilles and put down the martini glass. You say a polite “thanks but no thanks” to this f boy’s anger issues, his murder-y side. It turns out you are very happy to keep your name, and your sixth-floor walk-up.

Stephen DeMarco in Carola Lovering’s Tell Me Lies

Stephen DeMarco is a master manipulator. Deceitful and secretive, he uses people with little consideration for their feelings. He has no qualms about cheating on Lucy, going back and forth between her and another woman. His relationships are toxic and dysfunctional, on-again-off-again, because he intends for them to be this way. Naturally, Stephen is excellent in bed. 

This engaging book-turned-TV-series perfectly captures the heady, spectacular sensation of falling hard and fast for a f boy. We see why Lucy falls for him even though it’s an emotional train wreck. It is fascinating and horrifying to sit inside Stephen’s mind, and deeply satisfying to watch Lucy finally understand him, and the dark secret he holds inside.

Mr. Rochester in Charlotte Bronte’s Jane Eyre

Poor Jane. Initially, Mr. Rochester seems like a total catch (they always do). He’s intelligent and affluent and he treats her as an equal. He only asks that she ignore the strange noises coming from the top floor of his home. But on their wedding day, Jane learns Mr. Rochester is married and—it gets worse—he keeps Bertha, his wife, in the attic. He tries to pass this off with a simple explanation (Bertha is mad!) and proposes a new plan (Jane move to France as his mistress!) but Jane doesn’t find this compelling, and neither do we. Oh sure, Bertha is “mad.” Is she also “shrill” and “hysterical,” Mr. Rochester? 

In wonderfully karmic news, Mr. Rochester does pay a price for his behavior, losing an arm and an eye in a fire started by Bertha, making him the lesser known and rarely seen of all the f boys: the reformed f boy. He learned his lesson to treat people nicely the hard way which is why Jane eventually does marry him. He is, at last, worthy of her.