We’ve done TV characters a few times, but I can’t find a Shakespeare thread of this nature, so…
Supposing they were real people, which character from a play by Shakespeare (or “Shakespeare” if you’re a doubting Thomas) would you:
A. Marry?
B. Have a brief, but exciting fling with before breaking up and never speaking to them again?
C. Want as a family member? (specify your relationship to them. Parent, sibling, their child etc)
D. Want as a college roommate?
E. Really have hated in high school?
ooooh–my kind of a thread!
Supposing they were real people, which character from a play by Shakespeare (or “Shakespeare” if you’re a doubting Thomas) would you:
A. Marry? Benedick (“Much Ado About Nothing”)
B. Have a brief, but exciting fling with before breaking up and never speaking to them again? Oberon (“A Midsummer Night’s Dream”)
C. Want as a family member? (specify your relationship to them. Parent, sibling, their child etc) Puck (“A Midsummer Night’s Dream”)–he’d be a fun cousin.
D. Want as a college roommate? Rosalind (“As You Like It”)–she’s totally cool.
E. Really have hated in high school? Cressida (“Troilus and Cressida”)
a. Viola, in a heart-beat
b. Miranda
c. Prospero, as a kindly old uncle who teaches you tricks your parents don’t want you to know
d. Mercutio!
e. either Regan or Goneril…the bitches!
A: Marry? Desdemona (Othello) is perhaps the most devoted wife in all of literature. But I think I might be happier with Miranda (The Tempest)… With her upbringing, she’s gotta be a nerd.
B: Brief fling? You just know that Mistress Quickly (Measure for Measure, among others) is good for a few fun nights.
C: Family member? I could say Oberon (A Midsummer Night’s Dream), 'cause if he were a family member, that’d mean that I was a færie too. But that’s cheating, so I’ll go with Portia (The Merchant of Venice), probably as a sister. When you’re in trouble, you can count on her to get you out of it.
D: College roommate? The Fool (King Lear). Just think of the philosophical late-night BS sessions you’d have with him! The other fools would be good, too, but Lear’s is, I think, the best.
E: Hated in high school? Perhaps too obvious, but I would have an extremely low tolerance for Caliban (The Tempest), in any context. On the assumption that he wouldn’t have made it into high school, though, Romeo (Romeo and Juliet). The dude’s a walking hormone.
A. Marry?
Benedick, definitely.
B. Have a brief, but exciting fling with before breaking up and never speaking to them again?
Don John. sigh I love me a broody bad-boy. Oberon would be really, really tempting, but otherworldly relationships never end well.
C. Want as a family member? (specify your relationship to them. Parent, sibling, their child etc)
Beatrice as a sister. (Assuming I can’t be her myself!)
D. Want as a college roommate?
Puck. Can you imagine the hilarity that would ensue? (And penis, prob’ly.)
E. Really have hated in high school?
Polonius. He’d be that really annoying teacher always trying to relate to the students and giving endless pointless “advice.”
Fun one!
A. Berowne, Love’s Labour’s Lost. Less famous than Benedick, but along the same lines. Oh, and better :). He seems to be wordy and self-important, but he’s also very smart and funny, and much more sensible than any of the other comedic heroes. “Um, guys, maybe swearing off women for three years isn’t such a great plan? But while we’re at it, here’s a beautiful, eloquent speech on how love makes us do the wacky.” Oh, darling.
B. Harry. Percy. Henry IV, Part One. drool They don’t call him “Hotspur” for nothing, yanno. The wisecracking and constant snarking on authority figures would be fun for a fling but get old reeeeeal quick. But during that fling? Ah, bliss!
C. Based on her relationship with Celia, Rosalind would make a delightful sister (As You Like It). On the other hand, she would be both “the pretty one” and “the smart one” (Which, I’m middling pretty and smart, but not that pretty and smart), and I don’t think I could handle the competition ;). So – erm, Prospero seems like a good Papa to have. Maybe overprotective, sure, but understandably so, and once Ferdinand “proves himself,” Prospero accedes. Plus MAGIC, dude! “My dad could totally beat up your dad! With his MAGIC AWESOMENESS!”
D. Prince Hal! Henry IV. He’d know where all the great parties are (plus his friend Jack Falstaff can always hook you up with a brew, and Poins can trick you up a fake ID, and Gadshill knows all the bouncers…). And he’s probably spend most of his time at said great parties, leaving me the room to study and sleep. Awesome!
E. Cordelia, King Lear. Hell, I hate her now. The worst kind of brown-noser, the kind who isn’t really brown-nosing (EXCEPT THEY SO ARE). And everybody likes her because she’s so niiiiice and sweeeeet! Argh! I would be so tempted to, I don’t know, shove her in a locker or something. Or at least shun her at lunch. Hah!
I suppose I should give my own answers too 
A. Marry?
Who knew my favorite character was so popular? Benedick is everything I’m looking for in a real life guy, except for the whole being fictional thing.
B. Have a brief, but exciting fling with before breaking up and never speaking to them again?
Hamlet. The brooding intelectual thing would be neat for a while, but then get really old and I’d have to cut him loose.
C. Want as a family member?
Young Lucius. I’d adopt the little guy after his family is obliverated and give him a saner upbringing than he had so far in his grandfather Titus’ house.
D. Want as a college roommate?
Ariel. I know, no one knows Ariel’s gender, but I’ve seen a version of the play where Ariel was a “she” and that’s the conclusion I made while reading the play too, so there wouldn’t be any problems with room assignment. Ariel reminds me of Puck, but less mean and with a larger variety of powers.
E. Really have hated in high school?
Juliet. You’re in love with someone you just met and you’re going to marry him today?! Girl, put the romance novel down and take three steps away from the silly boy now.
It seems to be mostly women answeering this thread, so here goes at a man’s point of view:
A. Marry?
Beatrice
B. Have a brief, but exciting fling with before breaking up and never speaking to them again?
Titania – you know she’s got to be hot.
C. Want as a family member? (specify your relationship to them. Parent, sibling, their child etc)
Richmond, from Richard III, as long as I could be his second son (his first son died as a teenager).
D. Want as a college roommate?
Hamlet – a great philosophiser.
E. Really have hated in high school?
Rosencrantz and Guildenstern – or is is Guildenstern and Rosencrantz?
A) Ophelia–for some reason, I’ve always found nutty girls to be attractive.
B) Titania–OK, green memories with the Queen of the Fae would be very grand indeed.
If it hadn’t been for Claudius’ ambition destroying the Danish royal family and everything around it, Hamlet and Ophelia could have had a long and successful marriage. Ophelia was not always insane: she was only driven that way by Hamlet’s rejection of her and killing her father. That would drive most young women pretty crazy.
Hero from Much Ado about Nothing, as played by Kate Beckinsale. She just looked adorable in that picture.
Ooh, this is fun.
Marry–Benedick, no doubt. I need that bickering element to keep a relationship fresh.
Fling–Petruchio (The Taming of the Shrew). He has potential.
Family Member–I think Mercutio would make a great older brother.
College Roommate–That’s gotta be Puck. As WhyNot said, hilarity ensues. And hopefully penis, because I’d totally go for Puck. 
Hated in High School–Hamlet, the frickin’ whiner.
I have to go with Rosalind. She’s sane and she’s very smart and funny.
You’d have the intensity going with Juliet, but I don’t exactly want the aftermath on my hands. Maybe Kate is a better choice. You’d still get an intensity, but with more maturity and without the homicide.
I’ve always thought Prospero was cool, but on the other hand he’s very controlling. Maybe he’d be better with a son (i.e. my father) than he is with his daughter? If not him, then maybe Hamlet as a cousin I can talk to about philosophical things. Distant cousin, so I don’t get murdered.
Horatio. He’s a very good friend. I think you’d rather hang out with Mercutio a few times a week and then have Horatio in the apartment when you need to pay the bills, or want some quiet to study, or need somebody to take down your dying confession, you know?
Malvolio. He’s a prude and a tool.
Marry: Beatrice? Rosalind? Hard to choose. Smart women always intrigue me, thrill me, attract me, and cause me no end of grief. These two are hard to beat.
Fling: Cleopatra. Good for hot times, and then run as fast as you can. With her, you would want to make your move early–before it was too late. Dangerous, but fun.
Want as a family member: Lear, because he’s damaged and wise.
Want as a college roommate: Falstaff or maybe Jaques. Jaques is maybe a bit too close to a Hamlet, but I like him for his honesty. Falstaff, I guess I like him for his dishonesty. You really need two roommates anyway, so on further consideration, I’m taking both.
Really have hated in high school: Iago. Bastard. He would probably be the third roommate incollege too–the guy who it takes a while to figure out that you really don’t trust at all.
Oooh, fun!
A. Marry?
Sorry to be boring and repeat what everybody else has said, but I’ve got to go for Benedick. Or Berowne.
B. Have a brief, but exciting fling with before breaking up and never speaking to them again?
Edmund from King Lear. (I’ve always found him dead sexy for some odd reason.)
C. Want as a family member? (specify your relationship to them. Parent, sibling, their child etc)
Beatrice would be awesome as a sister, I think. Smart, fun, and fiercely loyal.
D. Want as a college roommate?
Emilia. Just going by that little scene where she and Desdemona are talking trash about men, she seems like she’d be a lot of fun once you get her away from Iago.
E. Really have hated in high school?
Pretty much the entire population of Venice in The Merchant of Venice, with the exception of Shylock and possibly Jessica. Racist yuppie bullies, the lot of them.
She does rob Shylock before she leaves with Lorenzo. Maybe Shylock was an okay guy once, if you believe when he was younger he might’ve been less bitter.
Just for grins, here’s an all Lear set:
Marry: Edgar
Fling: Edmund
Family Member: Uncle Kent
Roommate: Fool
Hated One: Oswald
The one I really want to marry though is the guy who wrote the sonnets.
A. Marry
I think I have to jump on the bandwagon and say Rosalind.
B. Brief Fling
Hmmm…well, Juliet seems to fall for guys pretty damn quick, so she’s probably easy. 
Either that, or Miranda, since the same can pretty much be said.
C. Family Member
Hmmm…an Uncle Prospero would be cool. Although having Gonzalo as a wise, old grandfather would be neat.
D. College roommate
Either Mercution or Trinculo. I had a Benvolio my freshman year, and it was no fun at all.
E. Hate in high school
Romeo and Tibalt. If I were around during the fight, I’d hope they would kill each other so I could go bang Juliet.
Eh, doesn’t matter.
Now, then, let’s think about this…
Marry: There are surprisingly few men in Shakespeare with whom being involved would not cause unpleasant personality transformation, madness, or death, so I’m going to have to join the Benedick harem, probably. Although I have to say, too, that I don’t like Benedick nearly as much when he isn’t Kenneth Branagh.
Fling: Prince Hal, pre-reformation.
Family member: Hrm. Horatio would probably be pretty good big-brother material. On the other hand, having an Aunt Cleopatra would be disturbingly neat…
College roommate: Rosalind, because she’s just cool.
Hated in high school: The four lovers in A Midsummer Night’s Dream. Annoying little twerps. And the entire cast of Measure for Measure. And Jaques, who’s one of those “Look at me, I’m SO PROFOUND” emo types. (So’s Hamlet, but he really is profound so it’s okay. ;))
A. Marry? Sigh. Benedick. I hate being one of the many.
B. Fling? Definately Oberon. Sparks, baby.
C. Want as a family member? Falstaff, the uncle who knows how to tap a keg.
D. Want as a college roommate? Wall, a nice quiet roommate
E. Really have hated in high school? Hamlet