Dean: take him home
Sam: take him home
Bobby: shake his hand
Anna: nothing
Ruby: warn her not to turn against Sam or turn him evil
Uriel: SENT TO HELL!!!!!!, cuz i bloody hate him
Castiel: thank him for busting Dean outta hell

Dean: seduce him
Sam: marry him
Bobby: ride shotgun with him
Anna: ask her about Heaven
Ruby: tell her that Sam is on to her, shake her up a bit!
Uriel: ask him if he prefers Hell to Heaven
Castiel: tickle him 'til he smiles. Bonus if he laughs!
:)

Dean: seduce him
Sam: smack him for using his demon powers and lying to Dean
Bobby: discuss supernatural theories with him
Anna: ask her about the impala sex
Ruby: stab her with her own stupid knife
Uriel: nothing
Castiel: tackle!hug him :]

Okay, I'll have another go, :D

Dean: sit and listen to him sing and play guitar
Sam: spend the day at a nudist beach
Bobby: have a backyard barbecue
Anna: ask her if she still would prefer to be human
Ruby: tell her not to show up while Sam and I are at the nudist beach
Uriel: get him to tell me jokes all day
Castiel: iron his trench coat! But he'd have to take it off first. Then I'd offer to iron his shirt, his pants, etc., etc.

Again? Lol!~

Dean: play hide-and-seek with him and not bother to hide
Sam: bodypaint him - FULL bodypaint him!
Bobby: help him bodypaint that beat-up Chevelle
Anna: ask if she's going to renew her relationship with Dean
Ruby: get her to supply the bodypaint and brushes - but that's IT!
Uriel: I'd say to him: "Live by the sword, die by the sword."
Castiel: spend the day patching him up and 'easing his pain', ;) ;), while he recovers from Alastair's ass-whupping

hahahaa! full body paint Sammy...niiiiice!!

Dean: hug him and get him some pie..and then some :D
Sam: ask him for a towel
Bobby: tell him he's awesome
Anna: ask her if she wants to be human again
Ruby: bitch slap her
Uriel: ask him if to tell me a joke, to see if he's that funny
Castiel: tell him it's ok to feel

Ha,ha!!! Ask Sam for a towel, love it!! Castiel: tell him it's ok to feel.........to feel what, Lucy?? bwahaha! :DDD

hehe...not telling, Wendy :D

Hey thanks for the heads up, 67impala! I didn't even know about this game! =D

Dean: hug him
Sam: smack him on the back of the head a la the pilot
Bobby: ask him to teach me japanese
Anna: ask her if she thinks there's a god
Ruby: ask her what the hell her true motives are!
Uriel: ask him if he's ever had sex ;D
Castiel: teach him how to fight

hehe, thanks Wendy, had a clue this was here, but I keep getting pulled away by This or That and Yum or Yuck!

Dean: smack him over the head for some stuff.
Sam: love.
Bobby: clean his house!
John: bring him back to life so I could beat him up.
Anna: fluff her cute wings!
Ruby: don't ask... I could get graphic.
Uriel: sue him for xenophoby!
Castiel: Make him listen to Queen all day!

Ooh, can we add other characters? In that case...

Dean: take him by his leather jacket and shake some self esteem into him!
Sam: hug him
Bobby: borrow his books
John: kiss him
Ellen: call her and ask where the hell she's been
Jo: same as above
Anna: ask her for the sword of lucifer so I can give it to the boys
Ruby: stick her in that devil's trap they used on Alastair and leave her to rot
Uriel: rip out his grace and make him live as a human
Castiel: shoot spit wads at him

Dean: help him prak the ghostfacers (they had it comin')
Sam: cut his hair a bit
Bobby: ask him to teach me how to make a devil's trap
Bela: borrow some stuff that she "took"
Ruby: torture her again like Alistair did
Anna: ask her how does it feel to fly
Uriel: sent him to a strip club
Castiel: buy him a new set of clothes

Yep, I think it'd grow a bit bleh if we just did Dean and Sam over and over again... or not :p

Dean: again and again!
Sam: recite Kylie Minogue's "Wow" to him.
Bobby: cook for him.
John: beg him to teach me to hunt!
Ellen: tell her she's a sweetheart.
Jo: nothing really, she's not the wind that rocks my boat.
Anna: Ask her if she thinks Cas is sexy, too.
Rubes: beat the shit out of her.
Uriel: throw him in Hell.
Castiel: just sit down with him.

Dean: Make use of the backseat of the Impala with him
Sam: Ask to borrow his laptop
Bobby: Move into his demon proof panic room
John: Ask him if he knew that Mary was a hunter
Ellen: Help her rebuild the Roadhouse
Jo: Apprentice her to Bobby
Anna: Ask her what she thinks of Zachariah
Ruby: Send her back to hell
Uriel: kiss him
Castiel: make him wear Bobby's "Kiss the Cook" apron and grill me a hamburger

Dean: Chill out with a brew and some Zep
Sam: Get into a water balloon fight with him. Then we'd just have to sit and, errr, talk! while our clothes are drying.
Bobby: Shoot tin cans off a fence with him
John: Help him clean all his weapons
Ellen: Ask her if she truly forgave John
Jo: Tell her she's too young and immature for Dean
Anna: Ask her about her past with Castiel
Ruby: Ask her what that smirk was all about
Uriel: Tell him I'm kinda sorry he got bumped off so soon
Castiel: Tell him to practice smiling in front of a mirror, ;)

LMAO !!!!!!!!

Dean: ask him if he'll let me drive the Impala (after I've softened him up in the backseat of course!)
Sam: Ask him if he still misses Jessica
Bobby: go on a hunt with him/have him teach me the ropes
John: Ask him if I can drive that big black truck of his
Ellen: set her up on a date with Bobby
Jo: Tell her that now that she's got a few years of hunting under her belt, she should set her eyes on Dean!
Chuck: Ask him WHAT HE SAW!

Dean : make lots of little Deans!
Sam : ask him for more evil!sam episodes (he was sooo much hotter!)
Bobby : share a beer
Anna : Help her find a personality...
Ruby : Help her find a new body, as this one can't act ;)
Uriel : Turn him into one of those nodding toys that people have on the dashboard of their cars!
Cas : Make lots of baby angels. Literally hundreds (you have to do your bit to help replace the angels that have died!!)

hahahahahaha
Good one Furrybert :]

lmao, furrybert!!

Dean : Love him
Sam : Play itching powder prank on him again lol
Bobby : Share a beer
John: Bring back for good to help the boys
Ruby : Kill her
Uriel :Punch him over and over again
Cas : Kiss him

Dean: Be best friends with him and have a car race with him.
Sam: Finish Stanford with him, marry him, then lots of other things that are on a need-to-know basis, and make lots of little Sammies that aren't hunters, just like he wanted!
Bobby: Talk to about supernatural lore
Anna: Ask her where she got her hair dyed, and can I get mine like that too?
Ruby: Torture her with her own stupid knife, then end it by stabbing her stomach, where she'll die...nice and slow.
Uriel: Kick him where it hurts, then let Anna take care of him
Castiel: Try to get some emotion out of him.

Dean: Have his baby
Sam: Have an affair
Bobby: becomes friends
Anna : Make sure she out of the picture
Ruby: Kick her ass
Uriel: first have him torture Ruby than turn him over to Anna
Castiel: Try to get him to laugh or at least smile

Dean: ask him if I can be just like him.
Sam: love him, marry him, have kids with him, and hunt with him.
Bobby: after what he said to my sammy, kill him.
Anna: be friends.
Ruby: kill her. she's a liar.
Uriel: kill him.
Castiel: tickle him. lol.

im going to another one

Dean:Marry him
Sam:Punch him a few times for nearly killing dean
Castiel:Bring him to the whorehouse again lol and congratulate him for becoming more like dean
Bobby:Cheer him up while he is in the hospital
Uriel:Continue punching him

Dean: kick demons' and ghosts' a*s
Sam: take him home and lock him in my closet so I'll have him forever

Haven't seen any of the other guys yet.

I'm making another one.

Dean: comfort him and love him.

Sam: marry him, have kids with him, hunt with him, and love him.

Bobby: kill him after what he said to Sammy in Sympathy for the
Devil.

Ruby: kill her.

Anna: kill her cause she wants to kill Sammy.

Castiel: tickle him till he laughs or smiles (I wanna see more of Castiel smiles) and hang out with him.

Uriel: kill him.

Dean : Ummm... lock him in my closet and never let him out.
Sam : Let my friend Sebbie have him. We made a pact.
Bobby : Ask him to teach me all his awesome knowledge.
Anna : be nice, because it's kinda sad...
Ruby :torture
Uriel : let he demons have him. They'll do a better job than me.
Cas : hug... steal his trenchcoat.

Dean : Love him and well.... let's just say the rest are not appropriate for a public website....

Sam : Cuddle up to him - its bloody cold here and that sasquach could keep me warm =)

Bobby : Chat and get him to teach me stuff

Anna : Hmmm...... use that blood things and send her back to heaven then run away with my Dean so she can't find him hehe

Ruby : Kill

Uriel : Kill

Cas : Hang out with and possibly a little angelic lovin? tee hee hee

Gabriel: Hang out with forever, have fun with his powers, and maybe some more angelic lovin..... hello Casa Erotica anyone? lol ;) I'll have me some of that lol

Bela: Get her to teach me the tricks of the trade =) oh and how to do good accents lol

Hugs all around! ;D

Dean: Hug him and tell him he's a good man and that he doesn't have to punish himself anymore.

Sam: Hug him and tell him he's a good man and that he did the right thing.

Bobby: Hug him and tell him that he's the best father in the world...especially because they aren't even his sons.

Adam: Ask him how they made him say yes to Michael...and hug him.

Castiel: Hug him and tell him he made the right choice when he backed Dean and defied Heaven.

Gabriel: Hug him and tell him that he's the bravest angel ever for standing up to Lucifer.

Crowley: Um...not gonna hug him. Ask him if Bobby's soul is really his own and if so, why did he give Bobby his legs back? Sure as hell wasn't out of the demonic goodness of his black heart.

Anna: Hug her and tell her that I forgive her and understand that she was just trying to do the right thing.

Ruby: Sure as hell not gonna hug her either! Make her watch as Sam kicks Lucifer's butt and throws his ass back into his cage.

LOL I like yours fanfly XD hugs all round is always a good way to go!

Dean: Go cruising in the impala with him
Sam: Sammy is also cruising with us but I'm riding shot gun ;)
Ash: Ask him to teach me enochian over a few beers in his blue heaven
Castiel: Go on a bender with Cas and laugh at his jokes because "it's funnier in enochian"
Bobby: Tell him how Super Mega Awesome he is (because it's true)
Gabriel: Go pranking with him xD (Nothing fatal of course)
Anna: Tell her Michael will roast her if she goes after Sam. Save yourself Anna!! :D
Ruby: Let Alastair torture her (he's the best right?)
Andy: Tell him to stay away from Ava!!

Can I make a new one, this time with more than two guys?

Dean: Drive me across the country in the Impala
Sam: Make out with him
Bobby: Have him teach me how to hunt every freaking thing in hell and on earth
Ruby: Stab her with her own blade
Cas: Make him teach me Enochian
John: Slap him upside the head and tell him not to make deals with devils!
Azazel: Keep the damn Colt and shoot the batard
Bela: Let Dean shoot her (just "not in public")