Three Chic Geeks

For the nerdy and proud. Warning: spontaneous geekgasms may occur.

Fictional Boys We Want to Date (Who Would Make Awful Boyfriends)


bad boyfriends

Valentine’s Day is coming up, and it’s time to think about to whom you’re going to profess your undying love. As dedicated fanboys and fangirls, we all have a few characters we are at least a little bit in love with. Or a lot in love with. Or obsessed with. You know, that kind of thing. True love won’t be stopped by the constraints of reality, after all – you are absolutely certain that Dean Winchester is the man for you. Great, but we here at 3 Chic Geeks have extensively gone through every one of our fictional crushes and picked apart all the reasons why they would NOT be good boyfriends. Read on to find out what we think would be the dealbreakers for each of the characters!!

1.      Sherlock Holmes

He’s tall, dark, handsome and British. He has impeccable taste and the voice of an angel. His eyes are like doorways to an alien galaxy. He’s a brilliant detective with a brain made for sexy, sexy deducing. Occasionally, he’s also a consulting dragon.

So what’s the problem?

Well… there are many. For one, Sherlock Holmes is a jackass. He has no patience for anyone he deems to be irreparably stupid – which, spoiler alert, is about 99% of the population of the universe. He will forget your anniversary, because it’s dull and it takes up too much space in his mind palace – space which he can use for storing more important things (like which brand of jam John likes best). If you enjoy having nice, long dates, forget about them now because half the time, Sherlock Holmes will be too busy for any of your dating nonsense – he will be off chasing a criminal through the streets of London, John Watson by his side. There will be severed heads in your refrigerator, violin screeching at five in the morning and any free time Sherlock has will be spent in the morgue or following John around empty warehouses. Of course, he might just be dating you for a case, and he will dump you when you’ve given him the information he wanted. About the only chance you have of having a fulfilling relationship with Sherlock Holmes is if your name is Doctor John Watson. Good luck.

2.      Legolas Greenleaf of Mirkwood

Beautiful, blonde, immortal, sassy and possessing a great head of hair, Legolas was a first crush for many girls who read Lord of the Rings in their youth (Freak Geek and Critique Geek being among them). Him being played by Orlando “Puppy Eyes” Bloom in the films didn’t help matters at all; after all, Orlando in a wig is bloody hot. He’s brave and he’s willing to put his hatred of another species aside in order to defeat a great evil and perhaps befriend members of aforementioned hated species along the way. Like, if Middle Earth had social justice bloggers (or Tumblr, for that matter), Legolas would TOTALLY be on that.

So what’s the problem?

Sorry to break it to you ladies, but Legolas probably bats for the other team – think about it, his “profound bond” with Gimli is a jar of glitter away from full-on gay. In the movies, his friendship with Aragorn takes on a homoerotic sort of air, to the point where some people who had not seen the movies but saw gifs on Tumblr assumed that Aragorn marries Legolas in the end. Also, do you really want to date a guy who will live for eternity, whereas you will die within the course of a century? Didn’t think so.

3.      Loki Odinson Laufeyson

How can I even begin to describe Loki Laufeyson? He’s flawless. His hair is insured for ten thousand Arabian stallions. He does horse commercials… in Nilfhelm. His favorite movie is Lilo & Stitch. One time, he met the Black Widow on a helicarrier, and she told him “Thank you for your cooperation”. And hey, one time, he threw Iron Man out of a window… it was awesome.

So what’s the problem?

Okay, girlfriend, let me break it down for ya… Loki is a narcissistic megalomaniac. He’s a frost giant who was raised knowing that frost giants are evil, so of course he has enough self-hatred stored within his heart to possibly beat out Dean Winchester in a self-loathing contest. He is the god of chaos, mischief and fire; do I really have to tell you this would end only in tears? Loki wants to rule the universe, and thinks everyone should kneel for him. He would murder you for shits and giggles. There have been reports of his secretly also being an escaped archangel on the lam, but those have yet to be confirmed.

Historically speaking, Loki has been reported to have an insatiable sexual appetite, mating with rocks, trees, horses, giants, walls, and whatnot – he’s like a cosmic demigod Jack Harkness. Be honest with yourself – do you REALLY want to come home to find him mating with a Shetland pony in your bedroom? And do you REALLY want to deal with being a stepparent to a giant ferocious wolf, a snake big enough to curve around the planet, a half-dead girl who rules hell and an eight-legged horse? Is his hair really worth it?

4.      Captain Jack Sparrow

Dreadlocks, pirate, played by Johnny Depp, incredibly sassy… what could possibly be wrong with him? Jack Sparrow is lovely. He’s a classy sort of pirate. He has style. If Hell’s Angels were pirates, Jack Sparrow would be their leader.

So what’s the problem?

Well, okay, how about the part that he’s liable to leave you stranded on a tropical island, being chased by an army of cannibalistic natives? Or the part where he will steal ALL of your eyeliner? Yeah, not cute. There’s also the fact that as a pirate, his bathing habits are probably spotty at the very least. Oh, and bid adieu to all your rum, because it will be gone very quickly.

5.      Doctor John Watson

He’s cute as a hedgehog, sweet and charming, a ladies’ man. He has those cute red briefs; he has those sexy doctor skills. He’s silly and he’s deep at times. He can romance the best out of anyone, and he’s not called Three-Continents Watson for nothing.

So what’s the problem?

John Watson has a dark side. That dark side is hidden well when you first meet him, but you only need to open the door to the fridge in the kitchen of 221B to find it. To start with, don’t expect to date John for very long; Sherlock Holmes will do his best to get rid of you as soon as possible, because chances are, he thinks you’re an idiot. Being kidnapped while on date is par for the course; I hope you brought your Mace. Dates are an iffy business, as they may come to an abrupt and unexpected end (or be canceled entirely) for any of the following reasons:

  • murder
  • arson
  • burglary
  • chasing after criminals
  • shootouts
  • attempted murder
  • Mycroft
  • Sherlock being drugged
  • Sherlock being on drugs
  • Sherlock possibly being on drugs
  • Sherlock having secretly had himself and John married

John Watson is so far in the closet that he’s bypassed Narnia entirely and ended up in Middle-Earth. Of course, there is one exception… Canonically, John Watson has been noted to be a great boyfriend… to Sherlock Holmes.

6.      Draco Malfoy

The Hair of Slytherin has it tough; his fangirls are so numerous that if he commanded them to kneel, Loki would probably be very jealous. Blonde and arrogant, he swaggered into our lives and pissed us off while being totally cute. Let’s face it, he’s a typical bad boy, and there are about a million girls ready to volunteer themselves at “redeeming” him on a moment’s notice. Oh, and he’s filthy rich and grew up in a fabulous mansion in Wiltshire.

So what’s the problem?

Aside from the part where he is a ferret, you mean? Well, you’re always going to come in second to his hair. He ain’t the Hair of Slytherin for nothing, honey. Possibly, you’ll come in third if Saint Potter, saviour of Mudbloods is on the scene. While his family is filthy rich and practically aristocracy, you have to keep in mind that he comes from a “dark” family. I bet you he was practicing the Unforgivables on hedgehogs by the time he was five years old. The Malfoys are blood purists, the wizarding world version of the KKK – so not fetch. And if Drakey-poo dared to date a mudblood, Luscious Malfoy would probably have said mudblood killed off in secret. Keep the bloodlines pure and all that, marry a half-blood at the very least.

7.      Severus Snape

Always. Always. Always turn to page 394. Severus Snape slid onto the scene and stole our hearts with a few well-spoken lines and a deep voice made for reciting Shakespearean poetry. He can brew glory and put a stopper on death – and he knows what a bezoar is. Sexy.

So what’s the problem?

Well… you know that sulky goth kid back in high school who sits in the back of the classroom, staring longingly at the pretty and popular girl, then after graduation joins a black metal band in an effort to become a “famous” rock star and “show” all those people that he has worth and isn’t just some slimy, pathetic wimp? And then he spends the next ten years singing to the Hot Topic tweens about the one girl he was in love with back in high school but never had a chance with? (Which, incidentally, is the whole plot of Avril Lavigne’s Scater Boi). Yeah, um… Severus Snape is like the wizarding world equivalent of this guy – except instead of joining a metal band, he joined a racist terrorist organization hell-bent on world domination. Not to mention that joining the Death Eaters when you’re a half blood practically screams “self-hatred”. He then goes on to spend the next seventeen years of his life as a teacher in the school he once loved and loathed simultaneously, sucking up to the children of Death Eaters, picking on Saint Potter and Longbottom while secretly working towards protecting the popular girl’s son from his old bandmate evil villain boss. He’s got things to do like kill Dumbledore and if he has to, he’ll kill you to keep his cover from being blown. Oh, and he’s still in love with Lily Evans. NBD.

8.      Dean Winchester

Disney princess eyes, check. Sexy car, check. Lips made for sin, check. Not good at the whole “resisting temptation” thing, check. He can shoot, he can fight, he can protect himself against almost any sort of supernatural ghoulie or beastie… and he knows all the best classic rock songs. Not to mention the whole mechanic’s hands thing.

So what’s the problem?

Well, first off, we’d be surprised if you managed to land a relationship with him and not a one night stand to begin with, seeing as the boy’s so far in the closet he’s probably found Narnia by now. He’s been to hell and back, literally. He’s basically a professional serial killer. His relationship with his brother is… unhealthy to say the least. He probably loves his car more than he could ever love you. Not to mention, you’re probably nothing more than a plot device, and are going to die a gruesome and painful death before the season’s over. Oh, and he’s in love with a confused angel who wears trench coat, and, you know, gripped him tight and raised him from perdition that one time, no big deal.


9.      Captain Jack Harkness

He’s got more confidence than most people, and he’s comfortable with his sexuality to the point where he’s estimated to be the only man capable of getting some sexy human on weeping angel action going. Blowjobs? He probably invented them. He’s traveled through time and space, and seen some freaky things while he was there. Oh, and he can’t die.

So what’s the problem?

Let’s start with the obvious… he can’t die. You will probably live for a century or so, and then die, sleep, perchance dream. Jack Harkness cannot die… it is the blessing and the curse bestowed upon him by the Bad Wolf. He’s a cosmic space-time whore with a chip on his shoulder and the ability to go anywhere in the universe at all should he choose to. Oh, and eventually, (SPOILER ALERT!) his body will be parted from his head and…well, let’s just say, the first time we meet Jack Harkness isn’t in Episode 9 of the first season of the Ninth Doctor… it’s in Episode 2. That’s right, ladies and gentlemen… (SERIOUSLY SPOILERS AHEAD) Jack Harkness is the Face of Boe. And yes, in the universe of Doctor Who, mpreg is canon. And Jack’s been pregnant AT LEAST twice that we know of. Feel free to be freak out now.

10.     Sam Winchester

Aw, look at that sexy moose, with his floppy hair and puppy eyes and the big brains. I mean, he was a law school student at one point, we know he’s bloody smart. He’s sassy as hell, too.

So what’s the problem?

EVERYTHING SAM TOUCHES DIES. If you sleep with Sam Winchester, you will DIE in the same episode. We are not even kidding. Like, it’s not even funny, you’re doomed the moment he smiles at you. Oh, have we mentioned that one time he had Lucifer waltzing around in his head for a while? THE Lucifer? Yeah, totally not sexy, unless you’re into that sort of thing, in which case we totally are judging you right now. Let’s also factor in that his job is professional serial killer, and that he’s probably just a little bit of a seriously attractive sociopath. And then there’s the rage he keeps locked away in his chest – let’s face it, it’s a good thing his name isn’t Bruce Banner, because if it was, we’d all be doomed. His incredibly codependent relationship with Dean (not even in the gay way) would probably stand in the way of a real relationship, but it’s not even a real concern – you will die a gruesome death before it can become an issue. No, seriously, everything Sam touches dies – and that’s the main point.

Feel free to leave us input on who you think should make the Terrible Girlfriends list on Facebook or Twitter!

Freak Geek would like to dedicate this post to her absolute favorite of all time band that you’ve probably never heard of, DuelJewel. Thank you for many years of beautiful music, and happy return to Hayato. Much love!! Lapidary forever! ♥♫♪

You May Also Like:

More Fictional Boys We Would Like to Date (Who Would Make Even Worse Boyfriends)

Fictional Girls We Love (Who Would Make Terrible Girlfriends)

Gift Guide: Valentine Ideas for Your Zombie Significant Other

The Sherlock Tumblr Tag Drinking Game (Or: A Study in Liver Disease)

Supernatural Drinking Game of Doom 


Author: Katherine Erlikh

I love candlelight dinners, long walks on the beach and killing demons. Usually you can find me at rock concerts. 90% of redditors believe me to be male. I'm pretty sure I'm Loki.

169 thoughts on “Fictional Boys We Want to Date (Who Would Make Awful Boyfriends)

  1. OH MY GOD! I can’t believe I just read your spoiler! Bad Chrissy. Bad. Bad. Chrissy. But like…I didn’t even realize. Until I realized. And then OMG Face of BOE!

    Also, I’m with you on everyone but Draco. Bring on Snape. Or better yet, Sirius. Bad boy with a bike? Yes please.

    • Trust me, I wanted to kill myself when I found out. This is why you shouldn’t lurk on Tumblr… I WAS ONLY LOOKING FOR A GIF OF HIM LOOKING SEXY I DIDN’T WANT TO FIND OUT THAT WAY I CAN’T POOR MY JACK *cries in corner*

  2. How did you leave Doctors 10 and 11 off this list?!

  3. Snape? Are you kidding me? *vomit* what about James Potter, Fred and George Weasley, Booth, Castle and the most important: Fitzwilliam Darcy.

    • We asked all our friends did a very scientific poll to get these answers. You’d be surprised how popular Snape is.

      • Yup, that’s what happened, we did a science and stuff. xD
        Yes, all of them had potential bad-boyfriend traits, but we felt that Draco Malfoy and Severus Snape were the two most beloved baddies that TOTALLY don’t deserve all the chicks they are pulling in. So, we featured them.

  4. How did you skip Spike? William the Bloody?

  5. Nothing will stop me from loving Captain Jack Harkness. Not even when he sleeps with half the galaxy. (That’s not an if. That is a certainty.)

  6. My god.. i would kneel to Loki.. don’t care if he is a psychopath. Damm you and your amazing looks Loki!

  7. Surprised Luke Castellan (Percy Jackson) and Tate Langdon (American Horror Story) didn’t make the list.

    This cracked me up though, it really did.

  8. Forget Dean and Sam – give me Castiel. Yeah, angels are junkless, but Castiel’s vessel Jimmy Novak is equipped for fun – and on the plus side, won’t burn out my eyes or make my ears bleed. Of course, there is the small matter that Cas is in love with Dean, but I’m nothing if not tenacious.

  9. If you do a second list, you should put Erik Destler from the 2004 Phantom of the Opera on it…I know so many people who love him but he definitely has things about him that would make him an awful boyfriend

  10. This was really perfect and the mean girls reference was even more so
    But spike!!!! And the 11th doctor.

  11. I would go for Loki anyway… we have many points in common *evil smile*

  12. But…. but…. I WANT THEM ALL. Even Snape (mostly because Alan Rickman is a fox).

    I have only recently discovered Supernatural (I’m on season 5 so far) and THE BOYS. omg the boys, I couldn’t even choose between them. Although, I have a slightly disturbing amount of crushy love for Castiel.

    Also, I *snort*LOLed at “John Watson is so far in the closet that he’s bypassed Narnia entirely and ended up in Middle-Earth.”

  13. I’m happy. The Doctor wasn’t on the list

  14. the creepy thing is I’ve had a crush on all these people. as for part 2, here’s a list: Harry, 10th doctor, Arthur, Merlin, Moriarty and Castiel.

  15. the creepy thing is that I’ve had a crush on all these. as for part 2, here’s a list: Harry, 10th doctor, Arthur, Merlin, Jim moriarty and Castiel

  16. Where in the world is Spike, Richard Castle, Doctor Horrible and best of all Captain Malcolm “Mal” Reynolds?!?!?!

    I demand a new (or extended) list!

  17. And so many bad ones from the old fandoms as well:
    Jim Kirk (any of the Enterprise bridge crew) will either love and leave you or get you killed.
    Starbuck or Apollo (old school) will marry you and you are guaranteed to die before the end of the ep.
    Han Solo…where to start. Has a price on his head from criminals and the government both, stuck on a set of twins (he kisses the girl, but ignores her requests, but does everything the boy asks) and ships with a 7′ tall nursemaid who sheds.
    Luke Skywalker: too many Daddy issues, plus that thing with his sister.
    Rick & AJ simon… count yourself lucky if you walk out of their detective agency alive with all limbs functional.
    Indiana Jones; barring a taste for 15 year olds, he regularly wanders into unsafe territory, gets his stuff ransacked by Nazis and rivals. Hope you have a taste for being used as a hostage by people who will throw you to snakes or cut your heart out.
    Let’s not even talk about the hazards of dating a mutant. (Although the primary drawback with Beast is shedding)

  18. Well there goes all my potential boyfriends… oh dear. HAHA

  19. Malcolm Reynolds should totally be on there! Hottt!

  20. Can we add Neal Caffrey to this list? I’d love to read your take on HIM.

    • I actually really want to, because I myself have a bit of a thing for Neal, but I’m not far along enough in White Collar to deduce him well enough. Perhaps same time next year?

  21. This is so ridiculously perfect I, as Tumblr would say, can’t even.

  22. Both Winchesters on one list? Nailed. It. 😉

  23. This was awesome and so incredibly accurate! Don’t forget The Walking Dead fangirls! Daryl Dixon…wooo-eeee talk about a hell of a relationship!

  24. You must add Tony Stark!!! XDDD and and Castiel!!! Dean’s angel of course!!! jajajajajajaja maybe Thor XDD Gabriel!! Michael!!! Lucifer, why not? XD *supernatural XD* oh God XDD this is way too funny XDD but poor Sammy </3 he can't have a normal love </3 Moriarty! and Mycroft! XDDDD
    Another note: LOKI IS WORTH IT! XDDD (?)

  25. I absolutely love this blog post! I have a total crush on Loki (never thought once about Thor!)…and that would be quite the scene with Loki mating with a Shetland pony!


  26. Oh my heart!! POW! Right in the feelings!
    Don’t forget Wolfy from The 10th Kingdom (Scott Cohen), Ardeth Bay from The Mummy (Oded Rehr), or Tommy Cahill from Brothers (Jake Gyllenhaal).
    My taste in men is strange but whenever these movies play…Yum, just yum.

  27. So what about Fictional Heroes that would make excellent boyfriends? *cough, cough* Steve Rogers *cough, cough* We need a follow up here 🙂 Thanks.

  28. A little older than the gents here, but how about Richard B. Riddick? That would definitely be an awesome death ride, but the ride would be worth it. lol.

  29. Captain Jack Harkness is also openly gay. Just sayin’.

  30. This is the best thing I’ve read today! Actual snorts came from me while at work making me look like a total twonk.

    Dean Winchester was my fantasy man for a long time, until he was irreparably broken in the head.
    I second all the votes for Spike & Malcolm Reynolds. And Neal Caffrey. And I put forward a vote for Eliot Spencer from Leverage. He’s hot, beats people up and is totally messed up.

  31. These are hilarious, but! Where is the Doctor? Or Malcolm Reynolds? Spike or Angel? The Salvatore brothers from Vampire Diaries? Jon Snow from Game of Thrones?

    Also, in the BBC Sherlock, Sherlock actually tells Watson that he is gay, so us ladies never stood a chance.

    • Actually Sherlock’s sexuality isn’t confirmed in BBC Sherlock… or really a thing. At all. Maybe. We’ll see what Season 3 holds.

    • Once you’ve watched all the episodes, and you go back and watch that scene again, this time nitpicking every detail we learned about Sherlock through all of seasons 1 and 2, it becomes apparent that he’s not identifying himself as gay, but rather identifying himself as asexual while defending Mycroft being gay… I thought that was one of the most fascinating and telling scenes in the entire series. 🙂

  32. I know I’m about to get rocks thrown at my head, but . . . I have never been attracted to Loki . . . or Sherlock. And I’ve always been too old for Draco and too young for Snape.

    I’d also like to say that I NEVER imagined Jack Harkness as boyfriend material. He is good for exactly 3 things:
    1) making the sex *eyebrow waggle*
    2) telling jokes
    3) saving your life
    Anyone who comes in contact with him can safely expect one of those things, and may even get all three! They do not, however, expect him to stick around.

    The Doctor, in pretty much ANY regeneration should have made this list.

  33. He’s a bit mature for this list, but Leroy Jethro Gibbs

  34. Uhm excuse me, I only have one thing to say…

    Hannibal Lecter.

    The end 🙂

  35. I’d love to see Prince Nuada Silverlance, and Eric (the Phantom from Phantom of the Opera):D Possibly two of my most favorite anti-heroes, aside from Loki, of course;p

  36. Jack Sparrow also has syphilis. That’s what that red sore on his cheek is.

  37. lmao i wouldnt be looking for “a boyfriend” when i approach malfoy.. if ya catch my drift..

  38. Loved it ladies! I just wanna see dear Malcolm Reynolds on the next one. You gals always make me laugh. 🙂

  39. Also, woo! DuelJewel! Thanks for the pointing in the direction of awesome!!

  40. Awesome! Definitely voting for Riddick, Prince Nuada, Ardeth Bay from the Mummy and Wolfy from the 10th Kingdom to be put on this new list! Also,…Loki…yeeeeah…kinda like ‘im. ;D

  41. Don’t forget Damon Salvatore and Azazeal. 😀

  42. Oh, and Lestat. Let’s not forget Lestat. 🙂

  43. sorry ladies but what about Tate from ahs?he totally doesn’t deserve our love

  44. What about Rumplestiltskin from Once Upon a Time? 😛

  45. Oh my god! I totally love Dean Winchester, and let me tell you that though all the reasons that you have given are completely valid but still I can never stop loving him

  46. Hey, you forgot some of the Vampire Diaries guys. Klaus would head my list, but don’t forget Damon and Stephan. They’re a danger in and of themselves.

  47. sigh, Dean Winchester stole my heart around season 2ish. But yeah, he is totally in the closet, in love, with Castiel. and his nerd angel loves him back. But the codependency he has going with Sam… Oi. They need an intervention, even Purgatory couldn’t cure Dean of that. I figure one day Dean will die for good and Castiel will make a little pocket heaven for them to live happily ever after in. 🙂

  48. There is incredible amounts of insight here as you really put your finger on the bad boyfriend material in our culture. (The Doctor being a bad boyfriend is a no brainer. He kissed another woman while being MARRIED for crying out loud.) Thanks for the truth!

  49. Agree with you on all but Legolas.

    You missed the real problem with Jack, though – he will sleep with any sentient being. You’d get alien STDs you never heard of and a lot of heartache besides.

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