Sergeant Cortez might be fun, although I think the heavy from TF2 would be cool also.

...Now that I think about it, I think I would want to chill with The Dopefish. If you don't know what The Dopefish is, then go taunt happy funball for all I care.

Sarge so we can beat those dirty "frontstabbers" the blues!
(If that technically doesn't count)
Imperial Guardsmen and train. For the Emperor! (Dawn of War :p)

Travis, Snake, Marcus Fenix, Kratos, Master chief, and (this is gonna sound so weird.) Mei Ling or Naomi Hunter.

Phoenix Wright in his hobo version: laid back and kinda sexy ;)

SimpleReally:
Duke Nukem

Me too. Dude knows how to fuckin party. "Shake it, baby."

Anyone from the Zelda games.

Preferably Midna. She's hawt.
Well, I don't think of myself as a fanboy...

Maybe The King of All Cosmos, just to see how weird the conversation would get when your talking about an ordinary subject.

Martin, from Oblivion. Its good to hang out with fellow emos.

TommyGun465:
Martin, from Oblivion. Its good to hang out with fellow emos.

On the other hand, could you imagine getting trapped in a lift with one of the beggar characters who just walk around the block and repeat the same thing to the same people over and over and over again? **shudders...**

TheIceface:
Sergeant Cortez might be fun, although I think the heavy from TF2 would be cool also.

Goddamn, how did I forget about Cortez? The most manly character in any video game, ever, just barely ahead of Duke Nukem.

Genis Sage from Tales of Symphonia. It'd be like having a kid brother who I actually enjoyed hanging out with. If you can play through Tales of Symphonia without laughing at something Genis says, you have no sense of humor. Oh, and his ability to manipulate the forces of nature virtually at will is always a bonus.

I'd love to drink grog with Guybrush Threepwood

that or go to stinky's diner with Sam & Max

i'm a big lusacarts fan

Max Payne. That guy feel off a cliff and got shot in the back, and is still alive. Nuff' said.

I'd say Duke Nukem just because I think he would be great to take to the pub.

mmh, that'd be postal dude for me, i might die in a horrible and painful way, (after being pissed on, and set to fire) but it'd still be awesome

The Engineer from Team Fortress 2. I want to learn how to make those sentries.

A white mage - free health care

Dude. totally Mr. Game & Watch lol

jackie esticato from the darkness garalt from the witcher or nieko from GTA4

Wavra:
Dude. totally Mr. Game & Watch lol

I have a friend who is a lot like Game & Watch. It's hard to explain, but he does some really random stuff. Like, you're in class, and you just watch him walk by from the left to the right. Then two seconds later he'll walk by from the left to the right again. I swear he has teleportation abilities. Also, whenever we play Smash Bros., he always tends to just randomly explode at random intervals. We usually play with items off, and occasionally we just see Kirby (his character) fly off the screen for absolutely no reason. Usually he's running towards a guy and he'll just go sent flying out of no where.

There are plenty of characters I like ,but the first one that I thought of when I read the question was HK-47. That guy is a riot.

My pick would probably be either HK-47 from KOTOR, or Wrex from Mass Effect, or GLaDos from Portal.

male_07 from Half-Life 2.

Apollo Justice and Trucy Wright. They are such a riot when they are with each other, and I'd love to see Trucy's magic, and just talk to Apollo.

CodeChrono:
Apollo Justice and Trucy Wright. They are such a riot when they are with each other, and I'd love to see Trucy's magic, and just talk to Apollo.

Where are they from? Just call me "Captain Oblivious", but I actually don't know where they're from.

Stammer:

bodyklok:
Gordon Freeman just for the conversation.

"Gordon?"

"Are you there?"

"HELLO?!"

"TALK TO ME!!" - At this point, officers, I just had to beat him to death with his gravity gun.

Good luck taking the thing from him.

Video Game character?
Hurm... I'd be fairly safe hanging around the big brawny Overwatch administration network, but then again, look at Breen.

So I have to agree with

Arntor:
HK-47

I'd have to say Yoshi, if anyone pissed me off I would have him eat em....either that or em at someone

or Navi from Ocarine of Time
"Listen!"

"Hey"
She could help me fight anyone who gets in my way....just press the Z button

I want to hang out with Doughnut from Red Vs. Blue. He's a video game character, right?

Yeah and for me it would be Kane from the C&C games I would just walk him around just to see peoples reactions.

Reasonable Doubt:
Yeah and for me it would be Kane from the C&C games I would just walk him around just to see peoples reactions.

You know, if you ever see Joe Kucan (the guy who plays Kane), and call him "Joe" instead of "Kane", he'll give you $10.

huntedannoyed:
I want to hang out with Doughnut from Red Vs. Blue. He's a video game character, right?

no.

No I am serious I am talking about Kane from the game not the actor his personality is odd and that would make my day to see what peoples reactions are to what he says.

Carmine from Gears of War

Well that would be interesting as I hear Cliffy B said he was alive after being shot in the head.

Reasonable Doubt:
No I am serious I am talking about Kane from the game not the actor his personality is odd and that would make my day to see what peoples reactions are to what he says.

I know. Just saying that if you ever saw Kucan...

Kane would be awesome to hang out with. I'd definitely ask him if I could be in his Inner Circle. Command an army against one of his finest to see how I would fare, then torture some GDI captives. Hell yeah.

I would personally like to be in his inner circle and see what was in that one room at the end of C&C 3 Tiberium Wars Nod ending.