In honor of Valentine’s Day tomorrow, I thought I’d write a fun listy-post about fictional leading men. Now, I’m a sucker for romance. There’s nothing I love more than a good love story, where a swoon-worthy gentleman does everything he can to win the hand of his special lady. But sometimes, right in the middle of all the warm fuzzies, a little voice whispers, Wow, that guy would be a terrible boyfriend in real life.

So, this is my paean to all the handsome fictional boyfriends out there who also happen to be obsessed, emotionally manipulative, or just plain damaged. I love you, but I wouldn’t want to date you.

Damon Salvatore, from The Vampire Diaries

Oh Damon. From the moment you swaggered onto our screens looking like a slightly sinister young Rob Lowe we couldn’t resist you. Your smoldering baby blues pierce us to our souls and your abs are splendid. Your undying (pun intended) devotion to Elena Gilbert makes us feel all fluttery and warm inside. Your day-drinking is as endearing as your penchant for breaking peoples’ necks.

Oh, wait. Maybe not that last one. On top of being an alcoholic and a blood-oholic, Damon also seems to really enjoy killing people, especially if, God forbid, they annoy him. He tends to show zero remorse, even when the new corpse in question is a friend or relative. Damon also spends a solid three seasons trying to steal his brother’s girlfriend, after spending one hundred and fifty years holding a torch for the evil vampire who lied to him, betrayed him, and turned him into a vampire against his will. So yeah, he’s beautiful, but that hardly makes up for being an obsessive sociopath with a rage problem.

Noah Calhoun, from the Notebook

This guy tends to top everyone’s lists of favorite fictional boyfriends, and I can see why. First off, he’s played by the delicious Ryan Gosling in the movie version. Moreover, he falls so head over heels in love with Allie that when she leaves for college he writes her a letter every single day for a year. Handwritten. Snail mail. That’s commitment. And even though she never answers a single one, he goes on to build her a Barbie dream house complete with porches designed for nudie-painting. This guy can carry a torch like whoa.

By which I really mean, stalker much? He knew this girl for what, three months tops? And don’t forget he bullied her into dating him by hanging off a ferris wheel and threatening suicide. This guy takes emotional manipulation to a whole new level. Sorry, Noah, the page-boy hat is cute, but I wouldn’t want to be your girlfriend.

Jace Wayland/Lightwood/Morgenstern/Herondale, from the Mortal Instruments

Part angel, all badass. Jace really knows how to kick some serious demon ass while wearing leather and slinging insults, but that’s not all. He’s fiercely loyal to his family. His acerbic wit can drive the strongest man to his knees. He’s hot, blond, and damaged. And I mean damaged.

Seriously, this boy has daddy, mommy and sister issues. He has no idea how to communicate his feelings without resorting to childish sarcasm. He’s reckless to the point of being self-destructive, flinging himself into the face of danger like he wants to die. His family tree is so convoluted that I actually had to go look up how many last names he has. But this is the disturbed cherry on top of all that: he was willing to get it on with a girl when he thought she was his sister. 

Ew. Just…ew.

Tim Riggins, from Friday Night Lights

Riggins #33. I didn’t even like football till I met you. I love the way you wear those jeans over your cowboy boots and never cut your hair. Your green eyes stare deep into me and whisper, “Love me. Hold me. Fix me.” Your Texan drawl sends shivers down my spine. You were really sweet to that kid whose mom you were banging…

But ladies, let’s be honest. Tim Riggins is a teenage alcoholic with daddy issues who is going absolutely nowhere in life. He stole his recently paralyzed best friend’s girlfriend. His brother is the absolute worst. Oh, and to top it all off, he’s borderline illiterate. He went to college for exactly 1 hour before driving back to podunk Dillon and tossing his textbooks out the window of his car. That’s no way to treat a book, Tim. Shame on you.

Mr. Darcy, from Pride & Prejudice

This is a hard one for me to admit. Mr. Darcy was my first hardcore literary crush, and I doubt I’ll ever really grow out of that. I mean, he’s a handsome enigma wrapped in an Edwardian coat and tied with a neat cravat. Master of Pemberly. Stern-but-loving brother to Georgiana. Loyal friend to Bingley. Savior of the Bennett reputation and eventual wooer of the clever Lizzy, our dear heroine. And don’t let me forget, he has ten thousand pounds a year.

But Darcy can also be a massive ass. He snubs Elizabeth (and nearly everyone else) in Meryton just because they happen to be a tad country and not fabulously wealthy and cultured like him. He ruins Jane’s chances with Bingley mostly because he feels like it. And when he proposes to Lizzy, he admits that he likes her despite her shameful nightmare of a family, horrific low birth, and complete lack of anything to recommend her. Wow. What a snob. (I tend to forget all that every time he dives into the lake wearing his white poet shirt, though. *swoon*)

Honorable Mentions

Sam/Dean Winchester–Just stay away. Both of them. Those boys are trouble.

Holden Caulfield--The only thing he has going for him is that he’s not a phony.

Aladdin–He doesn’t own a shirt, he’s homeless, and his only friend is a monkey. ‘Nuff said.