Shakespeare Characters’ Dateability, Ranked

You know how other people (some would even say “normal people”) like to talk about the movie or television characters they’d most like to date? Well, book people do that, too. Only instead of arguing over which of the True Blood men is the most doable, we turn to more literary sources. We aren’t always high-brow about it: I’ve played Kill-Fuck-Marry with more than one selection of Harry Potter characters. Sometimes, though, it’s fun to turn to the classics and try to decide whose pantaloons you’d most like to get into.

So, let’s get a little Shakespearean.

I know I'm not the only one who sat in class and at least thought about which of Shakespeare’s characters I'd hit it off with. Have you ever fantasized about Romeo confessing his love to you below your window? Or maybe you’ve imagined getting a little crazy with Lady MacBeth. Hey, this is a judgment-free zone.

I’m not ashamed to say I’ve put a lot of thought into this over the years. Like, a lot of thought. As in, enough to rank 25 of the most notable Shakespeare characters in order of whether or not you should date them, starting with the worst. Spoiler alert: If they murdered someone, they’re probably not partner material.

25. Iago, Othello

Best Boyfriend Traits: None. He’s a sociopath without any of the charm. Worst Boyfriend Traits: Psychotic, jealous, untrusting Bring Home to Mom? Iago is probably the last person on this list that you should bring home, and that includes crazy-pants Lady MacBeth. He’s a life ruiner, OK? He ruins people’s lives. He’s the Regina George of Othello.

24. Angelo, Measure for Measure

Best Boyfriend Traits: He’s better than Iago, but that’s about it. Worst Boyfriend Traits: Resorts to blackmail, will abandon you if you aren’t rich enough, may try to kill your brother Bring Home to Mom? He tried to blackmail a nun into having sex with him. A NUN. If you even consider dating him you have terrible judgment and I want to help you turn your life around.

23. Lady MacBeth, MacBeth

Best Girlfriend Traits: Ambitious, motivated, take-charge Worst Girlfriend Traits: Blood-thirsty, murderous, uses her sexuality for evil instead of good Bring Home to Mom? On one hand, Lady MacBeth is a strong, ambitious woman and we should respect that. On the other hand, she threatens to smash hypothetical children against a wall and stabs people. It’s a tough call, but I’m going to say no unless you like it really, really rough.

22. Petruccio, The Taming of the Shrew

Best Boyfriend Traits: Clever, quick-witted, not afraid of a challenge Worst Boyfriend Traits: Manipulative, a gold-digger, fond of mental and physical abuse Bring Home to Mom? If you’re into Stockholm Syndrome, Petruccio is probably the guy for you. But if you don’t want to be starved, denied clothing, and mentally toyed with, maybe take a pass on this one.

21. MacBeth, MacBeth

Best Boyfriend Traits: Ambitious, capable of feeling remorse, listens to his partner Worst Boyfriend Traits: Murderous, disloyal, easily swayed Bring Home to Mom? When you get him away from his crazy wife, MacBeth’s not such a bad guy. Everyone loves a man with ambition. He succumbs to peer pressure too easily though, especially when that pressure involves killing a lot of people.

20. Othello, Othello

Best Boyfriend Traits: Adventurous, honorable, well respected Worst Boyfriend Traits: Jealous, quick-temper, smothers women with pillows Bring Home to Mom? I understand that he’s a war hero and a great guy that (at one time) totally loved his wife, but let’s get serious. He smothered Desdemona with a pillow because Iago had her handkerchief. Mothers don’t like murderers.

19. Hamlet, Hamlet

Best Boyfriend Traits: Sensitive, romantic, asks a lot of questions about the worldWorst Boyfriend Traits: Neurotic, a little too obsessed with his mother, talks to himself a lotBring Home to Mom? Hamlet is like every guy you wanted to date during your first few years of college: seemingly deep, moody, and probably listens to a lot of Death Cab for Cutie. But remember, we all make a lot of mistakes during our first few years at school. Don’t let Hamlet be one of them.

18. Romeo, Romeo and Juliet

Best Boyfriend Traits: Romantic, not afraid to express his feelings, literally willing to die for you Worst Boyfriend Traits: Suicidal, stalker-y, fickle Bring Home to Mom? Let’s not even bring up his obvious issues with stalking and suicide. Remember how, in the beginning of the play, Romeo was ALL ABOUT Juliet’s cousin Rosaline, and then forgot about her the moment he saw Juliet? Had they lived longer than their four-day relationship, he definitely would have cheated on her. Can’t trust a player.

17. Portia, The Merchant of Venice

Best Girlfriend Traits: Intelligent, bold, knows a lot about the law Worst Girlfriend Traits: Manipulative, vindictive, kind of racist Bring Home to Mom? Portia might be rich and beautiful, but she has some stereotypical crazy-girl tendencies going on. Remember when she asked for the ring she gave Bassanio just to test him? Plus, that comment about not loving the Moor’s dark skin was not cool.

16. Bassanio, The Merchant of Venice

Best Boyfriend Traits: Romantic, great at guessing games, loyal to his friends Worst Boyfriend Traits: Probably wants you for your money, already kind of in a relationship with Antonio, will definitely give your ring away Bring Home to Mom? I’m iffy on Bassanio, mostly based on his extreme bromance with Antonio. Will you be happy always playing second fiddle to his best friend, especially when that best friend is willing to bankroll all of his crazy schemes and seems just a little too into him? Probs not.

15. Nick Bottom, A Midsummer Night's Dream

Best Boyfriend Traits: Comfortable in the spotlight, confident at all times, will totally go to Broadway shows with you Worst Boyfriend Traits: Arrogant, vain, sometimes has a donkey head Bring Home to Mom? He’s like every overenthusiastic theater kid you’ve ever met, plus a donkey head. But if that’s your thing, go for it. No judgment.

14. Titania, A Midsummer Night's Dream

Best Girlfriend Traits: Could take you to a lot of fairy parties, is a queen, kinky Worst Girlfriend Traits: Maybe a little too kinky, withholds sex for revenge, kidnaps kids Bring Home to Mom? How into animals/role-playing are you? Sure, she was under a spell, but Titania was still pretty enthusiastic about Bottom’s donkey head. Hope you can handle getting a little weird with this one.

13. Juliet, Romeo and Juliet

Best Girlfriend Traits: Will reject her family name for you, incredibly trusting, innocent Worst Girlfriend Traits: Suicidal, overly romantic, poor judge of character Bring Home to Mom? Juliet, girl, I get that you’re, like, 14, but someone needs to tell you that you shouldn’t elope with the first guy who climbs up your balcony (ahem). Caution, potential daters, this one’s a Stage 5 Clinger. After one night she’ll be willing to literally die for you.

12. The Duke, Measure for Measure

Best Boyfriend Traits: Will help you carry out your crazy schemes, just, likes going undercover (no pun intended) Worst Boyfriend Traits: Might try to marry you without your consent Bring Home to Mom? He’s the source of justice in the play and helps Isabella save her brother, which is cool. But he also just decides that he’s marrying Isabella without actually asking her. Consent, bro, give it a try.

11. Jessica, The Merchant of Venice

Best Girlfriend Traits: Willing to do ANYTHING for love (including lie, steal, and turn her back on her family and culture) Worst Girlfriend Traits: The aforementioned lying, stealing, and turning her back on her family and culture Bring Home to Mom? This one depends on how much of a family person you are. Personally, I’m a little iffy about someone who would steal from her dad, throw aside her upbringing, and run off with a guy who’s kind of a dick to her people. Where’s your sense of loyalty, Jess?

10. Desdemona, Othello

Best Girlfriend Traits: Trusting, ignores convention, follows her heart Worst Girlfriend Traits: Too trusting, needs to keep better track of her handkerchiefs, dead Bring Home to Mom? On one hand Desdemona is kind of a rebel, as she runs away with Othello despite the wishes of her father and some pretty awful racist comments. But, on the other hand, if you know your husband is coming to kill you, don’t wait patiently for him to do so. Not smart.

9. Katherine, The Taming of the Shrew

Best Girlfriend Traits: Thinks for herself, independent, outspoken Worst Girlfriend Traits: Abrasive, blunt, kind of violent Bring Home to Mom? Like Miley Cyrus, Katherine can’t be tamed (except by what’s essentially torture). Admittedly she’s a handful, but you aren’t afraid of strong women, are you? Feisty, smart, and not willing to put up with anyone’s B.S., Katherine’s who you date if you like your lady in charge.

8. Falstaff, Henry IV Parts I and II

Best Boyfriend Traits: Surprisingly insightful, funny, cares about his friends (sometimes, when it’s convenient) Worst Boyfriend Traits: Often drunk, fond of prostitutes, lies a lot Bring Home to Mom? This may be controversial, but I’m actually going to say yes to Falstaff. Sure, he’s corrupt, lecherous, and a bit of a joke, but he’s also a lot funnier and a lot more thoughtful than he’s given credit for. If you can get him to quit drinking and whoring long enough to talk to him, that is.

7. Mercutio, Romeo and Juliet

Best Boyfriend Traits: Loyal to his friends, witty, always up for a party Worst Boyfriend Traits: Proud, bad temper, dead Bring Home to Mom? Oh Mercutio, you came so close to being perfect. Charming, the life of a party, and so funny that even his death speech is witty. But he also essentially called Romeo a wimp and died trying to take on Tybalt himself, all for the sake of “honor.” Call me when you calm down with the pride thing, babe.

6. Ophelia, Hamlet

Best Girlfriend Traits: Loyal to her father and brother, innocent, loving even toward people who don’t deserve it Worst Girlfriend Traits: Suicidal, insane, has terrible taste in men Bring Home to Mom? As a beautiful young woman who seems to really care about the men in her life, Ophelia’s actually a pretty solid dating choice. I mean, she does kill herself, but that was mostly Hamlet’s fault. If you don’t yell at her to get herself to a nunnery, she probably could be girlfriend material.

5. Laertes, Hamlet

Best Boyfriend Traits: Loyal, passionate, willing to defend your honor Worst Boyfriend Traits: Quick temper, acts rashly, willing to kill for revenge Bring Home to Mom? Look, the poor guy is just trying to watch out for his father and sister. Sure, he kills a guy, but Hamlet kind of had it coming. I’m just saying let’s all give Laertes a second chance.

4. Viola, Twelfth Night

Best Girlfriend Traits: Has a great relationship with her brother, capable of making the best out of a bad situation, looks good in pants Worst Girlfriend Traits: Sometimes pretends to be a boy, attracts male and female nobility for you to compete withBring Home to Mom? I think you can tell a lot about people's character by the way they treat their siblings, and Viola’s love for Sebastian gives her a pretty good rep. The whole Viola/Cesario thing might get confusing at times, but just roll with it.

3. Rosalind, As You Like It

Best Girlfriend Traits: Looks great in dresses and pants, clever, admired by many Worst Girlfriend Traits: Sneaky, could insist on masquerading as a boy called Ganymede, you might have to compete with a decent number of men and women for her attention Bring Home to Mom? Brave enough to set off into the Forest of Arden, loyal to her family and her love, and looks great in pants. If Rosalind isn’t a Shakespearian catch, I don’t know who is. Plus, she’s all about gender-bending, so if you’re looking for a really progressive girlfriend, she’s a keeper.

2. Benedick, Much Ado About Nothing

Best Boyfriend Traits: Funny, charming, will agree to duel your enemy Worst Boyfriend Traits: Commitment-phobe, bad at expressing his feelings, cynicalBring Home to Mom? I’d be more than happy to enter into a “merry war” with Benedick. A funny, smart guy who appreciates a woman who’s just as witty as he is? Someone please tell me where I can get a Benedick for myself.

1. Beatrice, Much Ado About Nothing

Best Girlfriend Traits: Witty, caring, can be tricked into confessing her love for you Worst Girlfriend Traits: May ask you to kill someone for her, holds a grudge, her humor can be cruel Bring Home to Mom? In my eyes, Beatrice is the most perfect character Shakespeare ever wrote. Sharp-tongued, unafraid to speak her mind, and yet fully capable of expressing her love for those she cares about, Beatrice is the type of person that every man and woman should aspire to be with. Bow down before the best partner in all of Shakespeare.

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